Selling Intelligence (formerly Selling the Cloud)

General Episode Description:In Part 2 of this conversation, Jared Zelman, Founder and CEO of Othello AI, explores what happens when AI moves beyond helping individual sellers and begins transforming entire sales organizations.Jared shares his perspective on the future of sales management, explaining how AI can handle repetitive coaching, call analysis, and execution consistency while allowing managers to focus on higher-value leadership activities. The conversation examines how AI-powered coaching systems are changing the role of frontline managers and why sales leaders must rethink how they develop and scale teams.The discussion also dives into Jared’s founder-led go-to-market journey. From cold-emailing executives, investors, and industry leaders to building relationships with some of the most influential business figures in the world, Jared explains how disciplined outreach, persistence, and deep personalization helped accelerate Othello’s growth from startup to seven-figure ARR.The episode concludes with practical lessons for founders, CROs, and sales leaders on scaling efficiently, shortening sales cycles, achieving product-market fit, and balancing the art and science of selling in an increasingly AI-driven world.  What You’ll Learn:• The Future of Sales Management: How AI changes the role of frontline sales leaders.• AI-Augmented Coaching: Moving from repetitive coaching activities to strategic leadership.• Founder-Led Sales at Scale: How deliberate outreach can build customers, investors, and mentor networks.• Product-Market Fit First: Why founders should focus on learning and validation before scaling teams.• The Art and Science of Selling: Understanding what AI can teach and what remains uniquely human.Key Topics:• Managing AI-augmented sales organizations• The future role of sales managers• AI-powered diagnostics and coaching• CRM automation and systems of record• Salesforce versus next-generation CRM experiences• MEDDPICC automation and sales process intelligence• Sales velocity as a growth metric• Founder-led go-to-market strategies• Building relationships through cold outreach• Howard Schultz and executive networking stories• Product-market fit versus revenue growth• Shortening sales cycles• Why founders should delay hiring sales teams too early• The science versus art of selling• Human trust and relationship-building in sales• Scaling enterprise SaaS companiesGuest Spotlight: Jared ZelmanJared Zelman is the Founder and CEO of Othello AI, a real-time AI sales coaching platform designed to improve sales execution before, during, and after customer conversations. Prior to Othello, Jared founded Cicero, an AI-powered celebrity avatar platform. Through Othello, he is helping organizations scale elite sales behaviors while preserving the human elements of trust, empathy, and relationship-building that drive long-term success.  Resources & Mentions:• Othello AI• Salesforce• HubSpot• Notion• MEDDPICC• Howard Schultz• Steve Ballmer• Sam Altman• Paul Graham• Dale Carnegie• Costco• Lenovo• Science of Scaling by Mark Roberts• Entrepreneur.comKey Takeaway:AI can automate coaching, surface insights, and improve execution consistency, but it cannot replace the human side of selling. The organizations that win will combine AI-driven discipline with authentic relationships, strong leadership, and a relentless focus on understanding customers.🎧 Listen now and subscribe to Selling Intelligence for more conversations on AI, sales leadership, revenue growth, founder-led scaling, and the future of enterprise sales.KK Anderson (00:38)Okay, so you are, and we're gonna wrap up the second topic here with this question. You're reporting 10 to 15% win rates improvement, 8 to 10% reduction in sales cycle length, which is huge. ⁓ a lot of AI tools are making, some some pretty large claims like that. so like generally speaking, just w help us understand a little bit, like what what are you measuring over what time period?Jared Zelman (00:51)Crazy.KK Anderson (01:02)how was work to some of your success?Jared Zelman (01:04)Yeah.These are like guess depends, because ⁓ like some of these numbers are pointing time numbers, some of these are ⁓ like over a period of time. so if it's a period of time, these are like over a course of twelve months. what's unique is these are all for large enterprise, these are for Fortune one hundreds. When you see AI companies quoting crazy growth or performance metrics, it's because they're selling to a two person business in YC. in other words, bullcrap.Right. ⁓ these are metrics that are proven at some of the biggest companies in ⁓ multi-sectors. that said, the bar for the expectation the expectation of buyers these days is kind of ridiculous. frankly, if you're a sales tool and you're affecting win rates and you're not improving them by over 10%, that you're a failure.our minimum is like fifteen, we're aiming for like twenty five, thirty in some cases. Yeah, I mean w the buy the buyers are just so damn pro snickety these days. People's standards have gone through the roof.KK Anderson (01:49)wow.Mark Petruzzi (01:57)Beautiful. All right, let us move from topic two to topic three. Topic three is from rep consistency to overall CRO intelligence and how that impacts the overall management of an AI augmented team. And the first question I have on that is once your technology is levered across a team.What what changes for the manager? Because if the AI is handling execution consistency, prompting the right questions, catching objective handling in real time, the manager's job needs to change as well. So what does a great sales manager do differently when they have a productive and effective AI layer between them and the team?Jared Zelman (02:43)So we try to do three things in a closed up cycle. So we try to diagon it's kind of similar to like a I'll use like doctors as an analogy. We try to diagnose what's working, what's not working. So pretty much diagnosing what happens in sales calls, that stink. We then report that right back to the ⁓ to the managers and we give them a prescription. We'll actually give managers direct suggestions on what they should be doing differently to coach their team. Specifics, because managers they need specifics, they have a lot of other stuff going on.We will then actually implement that prescription. We'll then create the cure, hopefully, and reinforce those best practices in every single call. Right? And that system goes on, it's a close-up system. The way the manager job changes though is threefold. They now don't need to do all the diagnostics, they don't need to listen to 300 call recordings to identify the trends and what's working and what's not working.They don't even need to then draw the conclusions to how to fix that. Right? They can always be a human diluent director, but they don't have to do it from scratch anymore because of Thela's helping. Most significantly, they don't need to reinforce that training. They don't need to actually be sitting there coaching reps every single day, every single day. I mean, sorry, every single week. Because Thelo is doing that for them. So it's it's threefold. it's interesting. It's a point solution in that it's focused on sales calls.but it's doing every single part of that cycle such that the manager's job is similar, but it's not menial anymore. There is very little repetition in the manager's job when they have effectively an AI agent that is doing their journey work for them.KK Anderson (04:05)I would think that, as someone who has managed sales teams for many years, I find myself saying the same things, and as a sales coach, right, with our clients, I find myself saying the same thing to this, over and over again, like a broken record. And ⁓ it could be really interesting if you have to take away some of the fundamental that some of the repetitive stuff, like you said, it could be really interesting how those how thatvalue of that coaching conversation would change. So ⁓ and I'm curious to get your take on this as we're evolving. Like what do you see the future of of CRM? Right? We know every salesperson, hates logging CRM. I had this conversation with the CRO just today, like, our CRM is a mess. And it's it but it's still the crux of everything. I imagine that what you're what you'reJared Zelman (04:29)Yeah.KK Anderson (04:49)the notes you're pulling and the insights you're pulling on these calls are are feeding into CRM. Like what do you see the future of of CRM? Is it gonna be more in the background? Is it gonna be a big part of of the future?Jared Zelman (05:02)I think a system of record in general will always be a very important part of the future. It's also a good data layer which you need then to use AI on top of. ⁓ so it will always exist. I do think it'll look different. I will think it is good. I do think it will be one of the l last things to change though, and evolve. ⁓ I just like one prediction is ⁓ like look at Notion. I don't know if you guys have have you guys used Notion before? Great. we started to use Notion as our CRM. We use Salesforce and Notion. Kind of for different things.KK Anderson (05:08)No.Yeah, yeah.Mark Petruzzi (05:22)Do.Jared Zelman (05:27)Notion, although you cannot do 95% of the stuff you can do Salesforce, and you can do Salesforce with, ⁓ the 5% that you do have overlap is the most important 5%, which is like the standard, CRM part. ⁓ and it's so goddamn easy. Like, there's gotta be a way to have like notion level experience, but with the level of like complexity that you can have like a CRM today, like maneuver with. Like, I think thatKK Anderson (05:50)Give me an example.Jared Zelman (05:52)Like like here, like with Notion you can just copy and paste like a ton of content into. Like in Notion, you can even speak into it or like type into like a you can query it and it will then take that plain text query and create a database or input like content ⁓ into a database for you. Like in Salesforce, you can't even press enter and skip into a different field. You have to manually move your mouse or do a keyboard shortcut.KK Anderson (06:14)Yeah.Jared Zelman (06:16)Like that's insane. Like you need to like off in three times to get into Salesforce. We counted. We had to take on average nine clicks to actually make something happen in Salesforce to like actually start getting value. Like that's nuts. Nine clicks to get value? Are you kidding me? Like I have to off in to my CRM every 35 minutes. Nuts. ⁓ I digress.KK Anderson (06:18)Mark, are you listening?Yeah.Yeah. That's so interesting.Yeah. And so does it like how does how does ⁓ using a platform and a tool, a data layer like Othello Othelio, am I saying it wrong? Othello, Othello. How does that like how does that help the serum? Does it help with with forecast accuracy or pipeline or cleanliness orJared Zelman (06:47)No, a fellow, a fellow. Spam.Mark Petruzzi (06:49)Hello.Jared Zelman (06:57)Yeah, w we automatically sync notes into the CRM for you. We haveunlimited custom field mapping, unlimited custom objects. we're not trying to reinvent the wheel. I'll put that like put that out there. We are not changing your CRM forever, but we are reducing CRM note taking time by like eighty percent. Like I'll give you an example.KK Anderson (07:08)Yeah.Jared Zelman (07:14)We have a customer that's on a call, they're a medpic shop. Othello will automatically listen to the conversation, identify if MedPIC was achieved, the specific notes for each acron letter in the acronym, and we'll sync that into custom MedPIC fields in Salesforce for you, or HubSpot for that matter. That's great. Like that's a great next step, but like the future of CRM will be different entirely, I think. Like I would much rather in five years time my sales horse be completely like call it redesigned to look and feel like notion.KK Anderson (07:30)It really is.Yeah.Mark Petruzzi (07:39)Yeah,I'm with you on that one, Jared. ⁓ so we've seen a lot of AI tools adopted by individual reps. They'll they run off, they see something, they bring it in, and interestingly, many of those get abandoned a few months later because the overall workflow change was too high. Wasn't really, it was there was a shiny object that attracted them, notSomebody doing a real evaluation of what that product can do for the overall productivity of the team. So what does successful Othello adoption actually look like inside a sales organization? And what does the CRO or sales leader need to do structurally to get the team to use it consistently enough that the data really does become meaningful?Jared Zelman (08:27)So I like to we we actually have we're in a temporary office right now, but in our in our primary office in Israel we have a sign that says, You can lead a horse to water, but you can't make it drink. ⁓ words to live by when you're building tools for salespeople.Salespeople like me are not necessarily the most excited when it comes to new tools, especially when they're kind of being given to you by management. So it has to be super easy to use. Othello ⁓ is not there's no website, it's a desktop app. Automatically turns on when a call starts and starts listening. You don't have to click anything. There is no like look you how I said like Salesforce would click like eight times to actually interact with the product? Othello tr genuinely like zero clicks. Like you don't have to click anything.Mark Petruzzi (09:02)For sure.Jared Zelman (09:07)for it to be on and used in calls. So all the managers would need to do Mark is just download it onto their computers. And then Othello does the rest. You just need to read. Like I'm sure every seller in America is hopefully highly literate. All they need to do is be able to read the poppers of their screen.KK Anderson (09:21)Well, they better be if they're ⁓ the ⁓ core of our GDP here, our five million APs. ⁓ Okay, that's right. Okay, let's move on to our fourth topic. And this is the one that I've been most excited to dig into you with dig into with you. ⁓ and that's around the founders go to market playbook. And you have gone from zero to one million ARR in six months, which is awesome. Congratulations.Mark Petruzzi (09:22)Beautiful. All right.Jared Zelman (09:26)Yeah, it's ⁓ you know, the backbone of America. Yeah.KK Anderson (09:48)And so you tell the story, and I saw your write-up in entrepreneur.com about how you built Othello's early investor base through cold email, right? That you would email the CEO of Costco, the CEO of Lenovo, Howard Schultz. Like what walk us through that process that you followed. what you're describing is really contrary to what is prevalent out there right now, which is a lot of spray and prey, which has created so much noise and⁓ made it so much harder for our backbone of America to be able to sell successfully. So like tell us tell us about that. It's tell us about the discipline, the research, the kind of just tell us about your approach.Jared Zelman (10:20)Yeah.Yeah, so and look, there's goods and there's there's positives and negatives to my approach when it comes to getting in touch with the you want to get in touch with, because that's what it is. It's not just sales, just getting in touch with the people you want to get in touch with. ⁓ the bad of my approach is that it's a very direct. and I don't it's not pushy, but I don't miss words when I reach out to somebody and I'm very willing to follow up repeatedly. The good thing, I mean, you could say those are also positives, depends how you look at it.Right. Like if I want to get in touch withFor example, like the CRO of Microsoft or something like that. I don't even know if they have a CRO, but the CRO of Meta who I want to buy my product, like I will hustle like a mother, right? Cold emailing, cold calling him, sending gifts to his his office, his freaking home, get custom, Golden State Warriors jerseys for his kids with their names on it, some shit like that, until he responds, right? So to me it is like high pressure, it's full court pressure, right, to follow the basketball ⁓ reference.A lot of people don't subscribe to that. They support more of like a hey, like if you build it, they will come type of methodology. I don't believe in that. I don't have time for that. So when I was starting ⁓ Cicero and Othello, I said, screw it. Let's reach out to the people. And if they find value, they'll invest. And it was that cycle, actually. And it wasn't just for investors, by the way. It was our initial customers, investors, but like primarily I did it purely for mentors and to learn.KK Anderson (11:35)So howYeah.Jared Zelman (11:42)Like I was doing this throughout college. I didn't have a company to invest in. I just did it because I actually wanted to learn from like Sam Altman. I didn't think they'd really answer. Then I figured out they do.KK Anderson (11:50)Who'syour who's your the most shocking person that responded to you? Tell tell me that story.Jared Zelman (11:55)Say Maltman is a shocking one. I don't know if he's shocking. He responds to a lot of stuff actually. He's he's he's a I suggest you reach out to him cold. He's like known for responding to cold contact. Steve Bomber was a cool one. He was aKK Anderson (11:57)Yeah.Jared Zelman (12:06)That I looked up to for a long time. Howard Schultz was a cool one. So Howard Schultz didn't respond to me. And then he cold called me. don't know what it's cold called. He called me a few times. So I remember I was on the way to class in college and I got kept on getting a call for this freaking like Seattle number. And I thought it was some salesman. So I answered like a kind of a jerk. I'm like, who is this? is this Jared? I go, no.KK Anderson (12:25)Yeah.Jared Zelman (12:25)And Igo wait, who is this? It was so it was hilarious. It was like the stupidest thing ever. It was Howard Schultz. And I was acting like an idiot. And he found that to be also pretty funny. ⁓ so I was saying Howard Schultz co called me. It's kind of the same. Yeah. Yeah.Mark Petruzzi (12:26)Ha ha.KK Anderson (12:35)my goodness, that's amazing. Yeah.Mark Petruzzi (12:38)And Jared,KK Anderson (12:39)I bet you wishMark Petruzzi (12:40)there'sKK Anderson (12:40)you had a fellow then to tell you exactly what to say.Jared Zelman (12:43)Yeah, I feel like I I don't know, sometimes like the innocence of being y young is enough to get these people to give you time of day.KK Anderson (12:48)Yeah.Mark Petruzzi (12:49)So Jared, there's definitely some irony here. ⁓ you are the founder of a company that teaches reps to sell better. And you grew your company by being an exceptional seller yourself. So how intentional was that and what did building a fellow teach you about the craft of selling that you just didn't know before you started?Jared Zelman (13:00)Trying to be.Art for science, again, let's touch back on that. when it comes to selling, the art aspect of it I think is sorta summarized by falling in love with the person you're speaking to and getting them to fall in love with you. I could speak on both of those two points for a long time, we'll put a pin in that. So that's the art of selling. That's something that comes very natural to me. I wouldn't say I'm a good seller, I would say I'm good at that. Or at least I was good at that.After founding Othello, I realized the entire science aspect of sales. You can't teach art, but you can teach science. So we focus on doing that. And I've learned ⁓ just through building Othello so much more about running a proper sales process, how to run say real discovery that is structured as opposed to just being super interested, which is great, but it's not enough. So I wouldn't say I was a master salesperson. I would I'm not today. I was art,Sales artist, perhaps. Now I try to be a whole lot more than that.Mark Petruzzi (13:56)what, Jared, you're you're kind of defining a little bit of of my journey in sales where and even in from the standpoint of of a couple books that I've written. The first book, Selling the Cloud, was all about the art of sales. And that's really where I wanted to go first in in my writing. However, the s second well, a little background, I was actually ⁓Jared Zelman (14:02)Okay.Mark Petruzzi (14:20)Talked into and maybe even manipulated into writing a book. I'll share that story with the audience and the and ⁓ you as well another time. But I wasn't someone who wanted to write a book, I guess is the first thing, until we released the first book, Selling the Cloud. And then I could not wait to get to the science of selling, because that's really, as you put it, that's where theThe impact comes from, it's kind of there's only so much you can do to make someone who's not comfortable doing what you just described, building a relationship with someone, falling in love with them, having them fall in love with you, want to do business with you. that's that's harder to teach, but the science is pretty easy to teach when you really get it into play.Jared Zelman (15:11)The yeah, we don't really try to teach you the art of sales. We try to teach you the science of sales. Like and that's the human element by the way. That's why I think humans will always be in sales, at least B2B sales. Is for the art aspect of it. The science you can replicate, the art you cannot.KK Anderson (15:18)Yeah.Yeah, that's really interesting. And ⁓ at when as you perfect the science, then it gives the confidence and the bandwidth and the room for the art to really shine.Jared Zelman (15:36)Look, in theory, every extremely as I said, like the art of sales, I think is falling in love with somebody and getting them to in love with you. There's a lot of lovely people out there that can't sell for their life. but they they're they'd probably be great at the art of sales. So we try to get them to be more ⁓ more aligned with the science and best practices of sales.KK Anderson (15:43)Yeah.Yeah.Okay. So you went from Cicero, the AI Celebrity Chatbot Company. That sounds interesting. AI Avatars of Celebrities. Okay. And then now to Othello, you you did a hard pivot as you were describing. and you did it from scratch and you got to a million ARR in six months. Like tell us like how you did that. How did you validate I mean I you you talked a little bit about the research, but tell us tell usJared Zelman (15:59)Yeah, AI AI Avatars are celebrities.KK Anderson (16:18)Give us all your secrets, Jared.Jared Zelman (16:19)⁓ so I can tell you about Cicero as well because I I mean we did a million there. it comes down toKK Anderson (16:22)Sure.Jared Zelman (16:24)Look, it really is a it's a function of sales cycle length, is what it is. Like if you want to get sciencey about it. you could build the world's greatest business, but if your sales cycle like twenty-four months, and sometimes the world's greatest businesses do have really long sales cycles, the nature of their business model, then ⁓ you can't grow that fast on paper. like a lot of the fastest growing companies in a burgeoning industry are consumer because the sales cycle is like one minute.But in our business model, it was it's it's like four months and we were able to get it down to like a month. ⁓ so we could really juice the hell out of sales velocity because sales cycle was only a month. Maybe this that's ex that's like the hard part, and people don't think about that.KK Anderson (16:54)And how'd you get it down to a high?Jared Zelman (16:58)⁓ we like really workshopped the shit out of our sales process. We broke down everything across every sales process we were in at that point and prior to that looked at every commonality and we just started cutting out nonsense and built very strict SOPs, like extremely strict SOPs. ⁓ and we were surprisingly able to reduce it from four to one, which yeah.KK Anderson (17:18)And aren't you gonna say that you useyour own platform?Jared Zelman (17:21)Yes, but s but our platform helps with sales cycle lengths. It does. ⁓ but a b a bigger driver, at least of our type of business when it comes to sales cycle length is actually the stuff that happens off calls. Right? It's ⁓ touch points with InfoSec. how quickly can you get the business decision maker to actually sign something? Like that alone, like like contracting is the longest part of our sales process, or at least it was. How can you juice that?KK Anderson (17:24)Yeah.Mm. That takes forever. Yeah. Security.Mm-hmm.Jared Zelman (17:43)Yeah,I mean that's this is like sales. Like people try not to get into the science of it, right? But the speed at which you can close a deal is as important as your win rate in many cases.KK Anderson (17:48)Yeah.Mm-hmm.Mark Petruzzi (17:53)Excellent. So in general, Jared, you ⁓ especially after Cicero, you had lots of VCs that you could get to invest in your company. But yet you you did it a little more on the angels side, very famous angels nonetheless, people like Craig Jelinek and Howard Schultz as we described. But when itJared Zelman (18:14)How Howard SchultzHoward Schultz did an angel. He was a mentor. He did an angel. He missed the round program.Mark Petruzzi (18:19)Yep. Perfect. Cool. So having that, those relationships, ⁓ what's the one thing you would tell a founder in the audience who's at that pre product market fit stage and trying to figure out like what do they do? How do they if they're not a sales inclined individual, how when do they hire a sales leader and can you be a ⁓Jared Zelman (18:21)Never forget.KK Anderson (18:23)Ha ha ha.Mark Petruzzi (18:45)an inefficient founder selling sales organization for a period of time or to do you just need to make sure if you're not the sales leader that you bring one in right from the beginning.Jared Zelman (18:58)Yeah, I I I I strongly recommend against hiring for sales too early for thousands of reasons, many which are well documented already from people out smarter than me, like Paul Graham. ⁓ I think to determine when you want to hire a sales leader, it's funny, like people always say like hire the sales hire your first sales person like when you have not like no time on your hands but sales. That's actually misleading because it's very easy to fill your calendar with bullshit sales calls.It all comes down to reducing sales cycle to make it more efficient. I think you need to run that analysis on your sales process first, cut out all the fat. For example, if you're taking 30 meetings to close a deal, you need to understand if that's truly the minimum. I betcha it's not. And then once you have an efficient sales process, if you still have an absolutely full calendar, that's when you hire sales. Do not letFor example, like non-decision makers or like non-stakeholders waste your time. it'll convince you that you need to hire people because you're too busy, but you're not busy with anything meaningful, you're busy with time-wasting activities. So that's like the first trigger. Again, long way of answering pretty short questions. So I apologize, Mark, but it's important to get to the nuance.KK Anderson (19:59)Mm-hmm.Mark Petruzzi (20:01)No, it was a good one though.Jared Zelman (20:03)Also, and this is something that's I learned across all my businesses, is when you're launching a product for the first time, the objective is PMF, it's not sales, it's not product buyer fit, it's product market fit, which means post-sales defines success, but not actually the dollars in. ⁓ which means you want a short sales cycle, obviously, and you want a short time to value or renewal cycle. That's another way of graphing time to value. So you can determine PMF faster. ⁓ I highly recommend it before building a product that has a long experience cycle.You understand if you're really willing to take that risk. If it takes a year for you to prove value, you're at risk of investing a year in a product that will never have PMF, no matter how successful you are at executing. ⁓ that's one thing that you can control before you start a business. And I I implore you to think deeply about that if you're starting a business.KK Anderson (20:48)Jared, have you read ⁓ Mark Roberts' new book, Science of Scaling?Jared Zelman (20:52)I haven't I've been recommending that book a thousand times, I think, so I may just read it to start saying yes. Yeah.KK Anderson (20:54)It's so good. It's so it's sogood. Go on Amazon and get it. He ha he was on our podcast and a few months ago before the book released. But it's wonderful. We got to we got to do a pre read of it before it went to market. ⁓ but it talks a lot about product market fit and when to scale and yeah, it's really it's really great. Some good insight.Jared Zelman (21:11)He's great.I thinkyou need to have like made mistakes to learn this stuff. ⁓ and you almost have like need to have done it before. So that's like a good that's like a good like it's an underrated thing, like making mistakes. I would say like failure is super underrated. Yeah.KK Anderson (21:17)Yeah.yeah.experience. Yeah. It'sMark Petruzzi (21:29)huh.KK Anderson (21:29)whatit what makes it's what makes you stronger because when you come out the other side you're you've learned a lot of lessons. Okay.Jared Zelman (21:35)Yeah, you just wannamake sure you come out like yeah, still spry, but go ahead.KK Anderson (21:38)So so for our last few minutes together, we're gonna do our favorite section. ⁓ it's an audience favorite anyway. We call it rapid fire. And we've got a few questions and we'll ask them fast and give us kind of your in your first instinct and we'll go through it and I'll start. Jared, what's the first thing you've ever sold?Jared Zelman (21:56)ketchup sandwiches. Straight up, yes, honestly ketchup sandwiches, triple decker ketchup sandwiches.KK Anderson (21:58)Okay, I gotta hear about that.When you were a kid, ketchup sandwiches watched the neighbors at the swim meet? What?Jared Zelman (22:02)Yes.everywhere. ⁓ mainlyneighbors. ketchup sandwiches when I was like two years old. They were viral. And not in like the cool way, like viral isn't like viruses it's just very, dirty and I made them without washing my hands. Emphasis on gross. Yes. Emphasis on gross. For sure.Mark Petruzzi (22:13)So Jared, you really learned about gross margin really really early in there. I love that. You were you were just like I am notgonna over over ⁓ engineer this, that's for sure.Jared Zelman (22:26)They're actually delicious, by the way. I know that sounds terrible, but like, okay, you know what? I'm not even gonna I'm not gonna convince you. Trust me, if anybody some four two year old kid offers it to you in the street, give it a try. ⁓ sorry, that's not round of fire, but that's my answer. Sure. And like a lot more bread. Yeah.KK Anderson (22:37)It's just like a hot dog without a hot dog.Mark Petruzzi (22:40)Cool.All right. One one metric every CRO should add to their weekly dashboard that for most CROs is not there right now.Jared Zelman (22:52)Ooh, wow, I wanna think deeply about this one, actually. This is a fantastic question. You have to sue enough people and you build the best like weekly like deal agenda.I would I'm very much focused just the nature of our business on like sales velocity. ⁓ so it it it would be ⁓ leading indicators of sales velocity. And that's a that's business specific, but it would be a leading indicator of sales velocity. It could be something as simple as to touch on the InfoSec experience we were talking about earlier, KK. ⁓ the amount of times you had a touch point with an InfoSec contributor, or the amount of red lines you responded to in the course of a week. ⁓ that's something that like we we try we track that.KK Anderson (23:23)Interesting. Yeah.Okay, so Jared, who's the sales leader or founder that you admire and respect the most?Jared Zelman (23:33)Jesus Christ, these are crazy questions. I'm gonna offend a lot of people, depends on who I answer. if if all of my buddies watch this. Like I'll give you one, like ⁓KK Anderson (23:39)One of, one of.Jared Zelman (23:41)Like w we're doing we're doing work with Oder.com. ⁓ Kyle Norton, long before I started working with him, is like way long before, is a sales mentor of mine. Like he's a goat, so to speak. Dale Carnegie, when it comes to the art of sales, is a freaking legend. So I love Dale Carnegie. Though that'd say like those two are like opposite sides of the same spectrum.KK Anderson (23:58)Yeah.Good stuff.Mark Petruzzi (24:02)Beautiful. So ⁓ last rapid fire question. Hiff What's the biggest misconception CROs have about what real-time AAI coaching can and just cannot do?Jared Zelman (24:15)Well, the main thing is they don't know that it exists. so if they know it exists, ⁓ the conception misconception any of them would have is that it's ⁓ something it could become a crutch, right? Like if it's truly that good, why do we need salespeople at all? Why can't I just put like a the twenty-one year old kid in front of a camera to read off their screen?I think that conception is a misconception, because as we all discussed earlier, ⁓ you still need to have trust, you need to have empathy, it doesn't matter if you're using Othello or not, you can't replace the human element. So you can't you can't throw some random in front of a colleague's button perform well.KK Anderson (24:49)What you have shown us is that the best technology is built by founders who are great practitioners first, right? At the very skill that they are trying to scale. so if this episode, shifted how you are thinking about your rep performance or your AI coaching strategy, share it with your team, share it with your CEO, your VP of sales.We will put all of Jared's contact information and LinkedIn profile and link to his website in the show notes. We'll also reference the various books that we refer to in the in the episode. and you can find us at get-ags.com or anywhere, podcasts are found, Spotify, Apple, et cetera. And we're thrilled to have you, Jared. And until next time, thanks for joining us on Selling Intelligence.Jared Zelman (25:32)Thank you both. Talk to you soon.Mark Petruzzi (25:34)Thank you, Jared. Cheers.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Glenn Poulos joins Mark and KK Anderson to break down what truly drives success in complex enterprise B2B sales. With over 40 years of experience selling technical solutions across telecom, wireless infrastructure, and power utilities, Glenn shares the practical frameworks behind building trust, mapping decision processes, and creating repeatable sales performance.Drawing from his book Never Sit in the Lobby and decades of hands-on leadership, Glenn explains why buyers in complex sales are not simply purchasing products. They are buying safety, trust, and confidence that their decision will not backfire. The conversation explores how to slow down early, uncover real risk, build consensus across multiple stakeholders, and implement disciplined follow-up that keeps long-cycle deals moving forward.If you are leading an enterprise sales team or looking to scale predictable revenue in complex markets, this episode delivers actionable insight you can apply immediately.What You’ll Learn:• Why complex buyers prioritize safety and trust over price and specs• How to build trust early by slowing down and asking better questions• The importance of mapping decision makers and influencers in enterprise deals• How to prevent deals from stalling due to unseen stakeholders• The habits that create sales repeatability and predictable results• Why disciplined follow-up is a competitive advantage• How to coach sales teams before, during, and after every call• Glenn’s philosophy of greed-based learning and how it accelerates product masteryKey Topics:• Trust-driven selling in high-risk B2B environments• Mapping enterprise decision processes• Mutual action planning and consensus building• Sales discipline and behavioral consistency• Curiosity, preparation, and active listening• Scaling sales teams through repeatable behaviors• Coaching frameworks for enterprise sales leadersGuest Spotlight: Glenn PoulosGlenn Poulos is an award-winning author, sales expert, and serial entrepreneur with more than four decades of experience in complex B2B selling. He is the co-founder of Gap Wireless, which he scaled from startup to a multi-million dollar distribution business serving North America’s mobile broadband and wireless infrastructure markets.In 2022, Gap Wireless was acquired by the organization, where Glenn stayed on as Executive Vice President and General Manager to help integrate and grow the combined entity, now operating as NWS Canada.Today, Glenn serves as President of ProgUSA, supporting US power utilities and service firms with electrical test and measurement equipment. He is also the author of Never Sit in the Lobby, a practical guide to winning and sustaining success in complex sales environments.🎧 Listen now and follow Selling the Cloud for more conversations with leaders shaping enterprise sales, go to market strategy, and revenue growth. Subscribe wherever you get your podcasts.Mark (00:31)Welcome to today's episode of Selling the Cloud podcast. I'm excited to welcome Glenn Poulis, an award-winning author, sales expert, and serial entrepreneur with over 40 years of experience in complex B2B selling. Glenn is the co-founder of Gap Wireless, which he built from startup to a multi-million dollar distribution business serving the mobile broadband and wireless infrastructure markets.KK Anderson (00:57)and the infrastructure market.Mark (00:59)of North America. In 2022, GAP Wireless was acquired by Network Wireless Solutions, NWS, a portfolio company of green management. stayed on as the executive vice president and general manager to help integrate and grow the combined entity, which is now NWS Canada. Today, Glenn is president of Prague USA, a company that supports US power utilities and service firmswith electrical test and measurement equipment. Thanks so much for joining us here, Glenn, and welcome.Glenn Poulos (01:31)Thanks, Mark. Great to be here.Mark (01:32)Cool, so today we'll explore four critical themes. First one, the core of complex B2B selling. How deals really get done and when the product is technical and the risk is high, how do you make sure that you build very strong efficiency into your selling model? Building sales repeatability. The habits and systems that make results predictable.Scaling and distribution business. We're gonna go a little deeper in that than we normally do. But really from startup to exit in the telecom and technology sectors. And then AI and technology and sales. Using tools without using the human connection.Topic one, just start with the B2B selling model as a whole. Glenn, your book, Never Sit in the Lobby, is full of field-tested wisdom from 40 years in technical sales. When you're selling complex products, whether it's wireless infrastructure, equipment, or power utility testing solutions, what fundamentally determines whether a buyer says yes or ultimately walks away?Glenn Poulos (02:32)Great question. So, and we're talking about complex sales, right? So, right. Okay. Yeah. So, you know, complex sales is a little different than just, you know, box selling or when you're just selling commodities like printers and computers or something. And, you know, when, when someone's buying something that's complex, right, they're not really buying a product.Mark (02:36)We are. Yes.Glenn Poulos (02:52)I always like to tell our people they're buying safety and solutions, right? Like they've got a problem. It could probably be solved in many ways with a complex solution, right? And it, and they're buying the safety that it, the, that decision will work, won't blow up in their face. No one's going to get fired. That's where the old, nobody got fired for buying IBM or Hewlett Packard came from, right? And that someone will stand beside them when things get hard, right? The specs matter.but trust matters more, right? That's the most important thing is the trust. And if a buyer doesn't feel safe saying yes, price doesn't become an issue, product doesn't become an issue, you're kind of dead in the water. And that's just a little,Looking back, it's like that's why a lot of times people would say to them, so I can't believe I didn't get the order. Like I had the best product, I had the best price, I had the best delivery, but they didn't trust you. rather, and again, I love saying, nobody got fired for buying IBM, right? They knew IBM was going to be there even if they were twice the price. And it's like, you know what? I'm going to buy IBM. Then I don't have to worry about it. I can say, Hey, I bought IBM. What do you want from me? Right? So that's kind of my first part of it.so the question is like, how do you build safety and trust, right? That's the key, you know, and so one of the key things that I always say is, you build it by slowing down early, right? You got to ask better questions.Listening more than talking the old God gave you two ears and one mouth you do the math, right and ⁓ the so listening more than talking, know, and you want to you want to be open honest and upfront about the risks, right and Challenge them with the risks a little bit so that they're out there and you're discussing the real risks that are in play and when the buyer you were trying to establish report to the point where the buyer feels feels you're helping them and not pushing them to buyRight. And so that's, that's, that's one aspect of it. Right. And, you know, some of the biggest mistakes people make are, you know, pushing price too early, trying to dive into specs for bigger, faster, wider, deeper, 20 % cheaper, you know, all those kinds of, you know, salesmen kind of things. Right. And pitching before understanding. And yeah. So.KK Anderson (04:53)So in a complex sale where it could go on for six to nine months and there's lots of dollars at stake as we were just discussing, what are some tricks or ways that you teach or talk about building consensus as you go through the sales process, as new people are added on into the conversation, as complexities increase?you know, everyone's got a different opinion. Like what are some ways that you build, build consensus, if you will. ⁓Glenn Poulos (05:20)Okay, soor get to the order or whatever, right? I guess is yeah. So first, you got to understand the risk, right? Like that's the you got to present it to the customer, you got to present what the risks are to them and getting the job done. And you have to understand what the risks are to you and presenting your product at like your solution. You know, as being the as being the solution, right, you have to always remember early on and throughout it that buyers are not afraid of the price.And that proves itself out by just looking on the road and there's people that are driving Toyota Corollas and people that are driving Mercedes Benz S-Class, right? And so clearly some people just want to spend more on a car, right? And so they're afraid of being wrong, making the wrong decision. So you got to ask questions that uncover ⁓ what failure would look like if they make the wrong decision and who gets the blame if it happens, right? You're trying to identify that kind of stuff, right? And then second,This is so important, right? You wanna map the decision process, who influences, and there's many models and sales strategies out there. I don't teach these, but like the challenger model and what have you, where you're identifying the technical buyer, the financial influencer, the key decision maker and what have you. But you need to know, ⁓ especially the way I explain it to people is you have to look at the dollar value of the solution that you're selling.Let me, it's 50 K 500 K 5 million, 50 million. Right. And you have to say in the company that I'm selling it to who's signing that check, who's signing the PO, the authorization, the final, where does the buck stop? Right. Because if you're selling something that might be, you know, let's say, you know, 250 K and it's a $5 million company, it's probably the owner that's signing it. Right. But if it's, if it's a 250 K deal, but it's a $5 billion corporation.with offices around the world, chances are some vice president, regional manager, finance guy, whatever you need to map out and know exactly where you got to go to, find out why and where it's stuck. Right? So you're mapping the decision making who's the influencers, who decides and who could stop the deal. And, you know, and most of the time the complex deals fail because you ignored.the person you didn't know about or you were surprised late in the game who that was and that you never talked to. And sorry.KK Anderson (07:32)I think the key wordI'm hearing you say, Glenn, here is mapping. And we are huge fans of the idea of a mutual action plan or map, right? And so, and what's great about that is that not only are you mapping out the strategy of what's going to happen over the next six to nine months and who needs to be involved and who can say yes and who's going on vacation when, so you don't, you're not shocked at the end of the quarter when you're not getting a signature because you'reGlenn Poulos (07:42)Nice. Yeah, good. Yeah.KK Anderson (07:58)You know, the signer is in Barbados, right? But the trick I would think is, and I believe, is making sure that it's mutual. And so to the extent that you can really build trust by saying, hey, here's our plan, you know, when you have a champion, I think that action of creating a mutual action plan helps to really build that trust and build that relationship. And then as you're bringing new people in,it becomes easier because you're all singing from the same song sheet.Glenn Poulos (08:23)yeah, for sure. The there's a funny story in my I always like to say shameless plug for the book, right? But in my book, right, there's a story about a guy that sells high value tow motors, right? Like our forklift, some people call them. And these things are massively expensive machines, right? And $120,000 or whatever. And so, in the stories about a guy who shows up, he and he's trying to sell a companytow motors, right? And he works for Toyota. And so he looks at the organization and he says to himself, so they need like four machines. That's like half a million dollars. It's probably the CEO that's gonna, that could be the CEO that signs off on that, right? So what does he do? He calls the CEO and he says, hey, it's Glenn from Acme tow motors, right?You know, we want to show you the, these tow motors, they, know you're using Kawasaki, but you know, we'd love to get these in for a trial or whatever. the guys, what are you talking about? Glenn? says, I don't get involved with tow motors. the vice president of warehousing is responsible for all that stuff. That's Jack. I'm like, all right. Okay. Yeah. Fine. No problem. Let me give Jack a call. So call Jack.Jack, it's Glenn. was just on the phone with the CEO. He told me I really needed to get your attention. We've got these tow motors, right? We know you're looking at a few, you know, know you're a coil stock user. We want to show you the Toyota. says, Glenn, stop wasting my time. says, I don't get involved in that stuff. Right? I've got a director of warehousing. That's Bob. Right? Why wasting my time? Bob, Bob, I've been on the phone all day with the CEO, the vice president. They told me if I don't get these machines in front of you, you know, lickety split.Mark (09:41).Glenn Poulos (09:53)He's going to have my head. Right. And so, and he's like, glad, come on. I'm a director. I don't have time to look at tow motors. You got to talk to the warehouse manager. You know, that's Jack. Right. So Jack called Jack. Yeah. Of course, Jack refers you to the shop steward or whatever the floor manager or whatever. And before you know it, you're bringing in the tow motors. You say, look, I've been on the phone with the CEO, the vice president, the director, the manager, the, you know, the foreman. And now, you know, here they are. Right. So then you bring the machines to the, to the work.The whole idea behind that story is that at any point you can call anyone in the stack and figure out where the deal's stuck, right? And so, and one of the things I always like to do, and again, this is a metaphor, right? But it's very valuable and I've used it my whole life, right? Is he call the CEO and you say, look, I know you don't get involved in this stuff, but I got to, you know, I know you're putting half a million dollars of machines on the floor. got my machine down here and we're doing circles around Kawasaki right now. Like you need to come down here and have a look at this. And he's like,I need two minutes. That's it. And you know what the guy's saying? I'm tow motor ripping around my warehouse, brand new, whatever. I'm going to come have a look. And the CEO walks in and the, you know, all these people are like, what the heck's the CEO doing here or whatever. Right. And, but at any point you can call the CEO and say, why is my deal stuck? And then he says, well, Glenn, he says, I forgot to tell you, know, we have a deal with the national deal with Kawasaki and it doesn't expire until 2027 andAnd I mean, you want to figure that out from that guy as soon as possible. And hopefully before you delivered a demo or whatever. And, ⁓ but I like to try to give people real world examples of how it plays out and, what happens on the opposite side when people don't do it right is, you know, your sales guy says, ⁓ I, you know, I got an appointment to do the demos and it's now with the powers that be. Right. He, gave his report to the powers that be.He sent it upstairs, right? And all that stuff. I'm like, when salesmen tell me that makes me want to like blow my brains out, right? I'm like, who's the powers that be? You know, the people upstairs, right? And I'm like, no, those are the people that are buying your competitor. And you're going to come to me in a few weeks and tell me you lost, right? If you don't know that everyone in the chain and you can't call them, then you blew it. And the problem is you have to start at the top.and go down because you can't like start with the foreman and then he gives you the old powers that be and then start calling up the stack and alienating the guys below, right? You want to be pushed down, not up, right? And because, you know, it's like, how dare you call my boss, you know? And, and so that's like a real world ⁓ scenario of how it can play out in a way that people can relate to, right? So, and ⁓ yeah.And so I kind of got a little off topic. The other thing was, you you were asking me about, you know, how do you, how do you ramp it over time? Right. And, know, you, you always want to make sure all the trust is built before the brochures in the, and the pitching and the, know, you want to be sharing your insights and then you want to be playing to what you've learned. And you want to, you want to demonstrate and, and prove out only to that. Cause oftentimes mistakes I see guys make.is like a good example would be myself, but don't make the mistake of using yourself as marketing data because you'll probably be wrong. But when it comes to cars, I love Mercedes-Benz, but Mercedes-Benz is known for the speed and the AMG ⁓ motors in the car, and there's a lot of ⁓ very fastand very powerful cars, but that's not why I like Mercedes, right? I don't drive them fast. I mean, I do whatever the, whatever the proportional amount over the speed limit I'm able to drive is that's what I set the cruise at. And I, and I never, don't, you know, I'm not worried about dropping it down into third and going, you know, I'm what I like is the luxury and the comfort. I don't care about the speed. So, but most salesmen would start laying on 500 horsepower, dual torque, overhead cam, dual turbos, you know, new zero to 60. don't care.I'm already lost and I already know that you've not built rapport with me. Right? So how is it, he's not presenting to, you know, to sell $120,000 car to someone, you know, in the right way. Cause he didn't figure out what part of it's important to me. I don't even need to hear about the speed or the motor size. I don't actually care. You know, and it's the same with many, many things, you know, and, but people arethey're scared and nervous. And so they kind of like want to drop back to like the training, the bullet points they learned in the training class. You know, we do this, we do this, we do this, we do this, right? Whereas you want to be stopping talking and start listening. What is it you need to do with these? Why am I here? What is your biggest problem you're trying to solve? You know, is it quality throughput, timing, speed, you know, power, you know, accuracy, know, resolution.Whatever, you know, so sorry, I rambled. I said it.KK Anderson (14:40)makes perfect sense. It really does. Andlike it, this kind of is the perfect bridge into our second topic, which is around building sales repeatability, right? And the habits, you talk a lot about habits. As a matter of fact, on LinkedIn, I reposted one of your posts this morning around the habits and the systems that make results predictable. And so in your book, you outline57 winning sales factors and that's a lot of variables. And so when leaders hear that, their first reaction is probably something along the lines of how do I make 57 factors repeatable? So if you had to distill it down, are there three to five that are the most? Yeah.Glenn Poulos (15:07)Yeah.Sure. Yeah. I love him. Yeah. Yeah, sure.Yeah. yeah. And so, and just to touch on the 57 and the number, and I mean, obviously I'm not gonna run off 57 of anything on the show, but the...KK Anderson (15:31)Yeah.Glenn Poulos (15:34)But these are factors that cover the whole litany of things you have to do during the day and throughout your career in order to be successful running the business and in sales, right? And so it's selling and so it's how to get act and stay in front of your customers and be a pleasure to do business with always, right? And yet you have to be a pleasure to do business with because most big customers are repeat customers. And so it's not a one and done, right? It's not like, you can be cranky with them and get the deal and then you're good because you got the deal becauseAll the customers I work with, they're 20 year investments of time, right? They buy with for me forever, right? And the company Gap Wireless, I started in 2007 and the first call I made, you know, was a lady named Arefa and I was still making calls to Arefa the day I left, 20 years later, 18 years later, right? and so the...And so then another insight into the 57 is these are rules that I always follow. I don't break my own rules. Right. And so, and the book never sit in the lobby. That's one of them never sit in the lobby. Right. And we can talk about that later. If there's time. Why, why I say that. but the habits to be repeatable, I guess would boil down to as first as you want to be prepared. Right. And so you've done your research, you know, you're selling this kind of a system to this kind of a company.What does this company do? How does this company make its money? Because they don't care about your system, right? They care about whatever goes out their back door and with the invoice and what they get paid for doing, right? And so again, a quick story. I always like to put this in the real world so people understand, well, what do you mean, right? Or it's not just hyperbole that I'm saying. It's like Xerox, right? You're calling on Xerox, right? Well, Xerox makes photocopiers.And so I need to figure out about, you know, how they can make better photocopiers. No, that's actually not what they do. They're a bank, right? They're a finance company. They make all their money, you know, on either one leasing you a machine or two, selling you costs per page, right? They don't come and tell you that that photocopier is 40 grand. They tell you it's four cents a page, eight cents a page, nine cents a page, minimum thousand pages per month, you know. And soYou need to understand how the company makes money. So you want to be prepared, right? ⁓ You know, so, and you want to keep and always be prepared, right? Second thing in the repeatability stack is, you know, discipline follow up. And so this is where people get scared, lazy. They're just averse to it. Right. And so, so often you say to him, like, did you follow up? And he's like, yeah, I, I, I call them.And okay, did you call him? Okay. Did he answer? No. I left the voicemail. Okay. Did he, what'd you say on the voicemail? And you know, maybe he says it and again, there's rules on leaving voicemails in the book, but, then I'm like, okay, well then what'd do? He says, well, I sent him an email. Okay. Okay. Did he reply back? And no, no, he didn't reply back. And so I'm like, okay, so let me get this right. So you emailed the guy, didn't reply. So you call them, left a voicemail. He never phoned you back. And so, so basically you'd never talked to the guy.Right? Kind of thing. But you have to, you have to be able to figure out ways and means to be able to follow up and stay on top of it. And what ends up happening is, is, know, you call him, he doesn't answer. So you send him an email and then you say, follow up Monday, right? Monday comes at a fight with your spouse. You're not in a good mood. You didn't get enough coffee. You don't really feel like making the call. You snooze it to the next day. And then the next day you have meetings. You're like, I didn't do the call. Damn snooze it to the following Monday. Now you're two weeks away.Right? Like, I mean, that's not discipline, it's avoidance and it happens like a thousand times over every week with a thousand salespeople. Right? And so you want to be disciplined. and whatever that means. Right. And, you know, and the deals are always one after the meeting. Right. And so, third, you want to be taking good notes. You want to be, and then reflecting on what's happened, what's happening.you want to be reviewing sort of the conversations and then looking insights. And that's where I teach, sympathy, empathy and compassion, right. And trying, trying to put yourself in the customer's shoes, figuring out what they're dealing with, et cetera, right. And applying the right technique at the right time. and you want to be reflecting on those conversations, like I said, and taking the notes and following them up. Right. And then, and so those are sort of the keys, but some of the other elements, you know,was curiosity and ⁓ you never want to assume, you know, there's the horror story where I in the book about me assuming something about a guy and I just made him so mad by my assumption. And I was just very difficult to establish rapport after that. Right. And and you want to be consistent. Right. You want to always be a pleasure to do business with, even when they say you're not getting the order.because you'll get the next one or you had the one before or you want to be called back in a year from now because you don't want them to not call you because they know they upset you and they're scared of you, right? It's like, I'm not calling Glenn. Pardon my language. He snapped the last time we, you know, we couldn't buy from him because of a, you know, a minor issue and, you know, a technical anomaly or whatever, right? So that's how I beat repeat. That's how I build repeatability.Mark (20:22)Yeah.Perfect, good, well, yeah, those are some good thoughts and ideas. So Glenn, you've built multiple companies and have hired and managed dozens, maybe even hundreds of salespeople over the years. When you're trying to scale a sales organization, when you're trying to bring these principles into a team, how do you transfer what's in your head and in your book to the team? How do you make your processyou know, more easily teachable.Glenn Poulos (20:50)So.Well, you know, how do I transfer? mean, you have to break it up into the behavior that you want and not just the talent, right? So repeatable behaviors create talent of itself, right? That's why when you look at sports people and all that, they're always doing the basics, right? You know, it's like, they're like NFL players. Why do they have to keep doing that same thing with the running with the legs and the tires? And because, you know, because they're building, they're building the talent through a set of behaviors, right?So, and you you wanna be teaching what you do before, during and after every call, right? So we're gonna go in there, we need to figure out what it is the problem is, know, da da da da. So then you're trying to coach them during the call. And then after the call, you're like, Jack, what went wrong on that call?Right. ⁓ I was talking too much. didn't, I saw there was an opening. didn't take it. You know, we could have got a referral to that. You know, he kind of deflected that it was another team was involved, but you didn't get any names, you know, so you want to be, you want to be, coaching before, during, and after. Right. and you know, I always like to say, you know,Like the methodologies are the frameworks, but the winning factors are the behaviors that you follow. And you can follow a methodology and still lose because you, I would say you ignore the basics like respect, timing, preparation, follow up, what have you, right? And they all build on each other and compound into being more of a disaster the more you fail at that, right?And so, you know, and then you're like, then the question is like, how do you pass, how do you teach people and how do you pass it on? Right. And so one of them, that's a highly personalized ones, it's from the book, right. It's my, my philosophy of greed based learning. Right. And so, and again, I hope, hope I'm not going on too far if I'm spending too much time on each one of these topics, but, greed based learning is the key to how I've sold technical products for 40 years. Right. And I, and I realized that.you know, a long time ago and, and I allow it to, I allow it to, to work in my day to day, you know, behaviors, right? So what greed based learning is, is that, and again, I use an analogy, I love to use buying car analogies because everyone has a car. And soLike I told you earlier, I don't care about the horsepowers and stuff on cars or whatever, right? And don't even actually care. I just want to be comfortable in a nice car and whatever with the gadgets and the cruise and all that. Right. But, you know, and so I don't really know a lot about cars where other guys know every spec off the top of their head. Right. But every four years, you know, I get a new car or something like that. Right. Well, you can bet for the, for that very small snippet of time. And for me, I'm probably going to be looking at, you know,Mercedes, BMW, Volvo, something like that, right? And you think I can't go home and talk to my spouse and spout off every speck of those cars that I'm looking at off the top of my head with little need for memory, right? And it's a thing that I call, that's why I call it greed-based learning because my greedy little nature knows I'm getting a car at the end of it, right? And I'm able to absorb those facts painlessly and effortlessly.Right. Because I'm getting something at the end of it. Whereas if someone just said, here's a 40 car manufacturers in the, or, car companies in the U S right. Learn all the, learn all the facts about all these 40 cars or whatever. be, it would be categorically impossible for me. There's no win in it for me. Right. And so, what you want to do is you want to sort of defer your learning until it's relevant to something where there's something in it for you. And then it becomes effortless. Right.You're selling a million dollar system to a company you can bet that you're going to be able to remember the facts because you know what your commission is on it. Right. And so I show these guys how to allow greed based learning and gals to in their, in their career. Right. And so it's just a little, a little gamification on the, on, on learning that I do. Right. and if I have an important call with an important piece of equipment on a company and I don't really know the box,And whatever I'll call the manufacturer, I'll call the product manager. I'll say, give me the five things they need to know in order to be a rock star with this product. And if I get stuck, I'll call you from the, from the customer site. And, and they're like, well, it's this, this, this, this, and this, right? And I'm like, look, I'm not the expert, but these are the things, you know, and then you're again, you're probing and learning and what have you. Right. So, that's the basics of it.Mark (24:52)No, thinkSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Mark Petruzzi and KK Anderson are joined by Jason Baumgarten, Global Head of the CEO and Board Practice at Spencer Stuart, to unpack what truly separates sales leaders who advance into CEO and board roles from those who remain stuck at the functional level.Drawing from more than 250 CEO and board transitions, Jason shares a rare behind-the-scenes perspective on how boards evaluate CROs, why ambition alone is not enough, and what sales leaders must change as they move from execution to enterprise leadership. The conversation explores founder-led transitions, boardroom presence, customer lifecycle thinking, and why sales excellence alone does not guarantee executive readiness.This episode is essential listening for CROs, founders, and revenue leaders who want to move beyond quota and operate at the highest levels of leadership.What You’ll Learn:From CRO to CEO: The mindset shifts sales leaders must make to be considered for top executive and board rolesBoardroom Credibility: How sales leaders can show up as strategic business operators, not just revenue ownersFounder Transitions: When founder-led selling breaks and what must change to scale the organizationSystems Thinking: Why understanding the full revenue and customer lifecycle matters more than pipeline aloneExecutive Readiness Signals: What boards look for when evaluating senior sales leadersHiring at the Right Time: Common board mistakes when transitioning away from founder-led salesKey Topics:Evolving from sales operator to strategic executive CRO presence and influence in the boardroomFounder-led sales versus scalable go-to-market systemsRetention, lifecycle metrics, and long-term growth signalsBoard governance and leadership transitionsWhy sales is not always the answerGuest Spotlight: Jason BaumgartenJason Baumgarten is the Global Head of the CEO and Board Practice at Spencer Stuart, where he leads executive search and board advisory engagements for companies ranging from early-stage ventures to multi-billion-dollar enterprises. He has advised on more than 250 CEO and board transitions, with deep expertise in founder-led technology companies, succession planning, and board effectiveness.Before joining Spencer Stuart, Jason was an Associate Principal at McKinsey and a Program Manager at Microsoft. He holds an MBA from Stanford Graduate School of Business, serves as Chairman of the Board for IslandWood, and is a frequent contributor to Harvard Business Review, including his article How CEOs Build Confidence in Their Leadership.Resources & Mentions:• Spencer Stuart• Harvard Business Review: How CEOs Build Confidence in Their Leadership• Mark Roberge: The Science of Scaling🎧 Listen now and follow Selling the Cloud for conversations with leaders shaping the future of go-to-market, executive leadership, and board-level decision making.Mark Petruzzi (00:37)Welcome to today's episode of Selling the Cloud Podcast. I'm thrilled to welcome Jason Baumgarten, Global Head of the CEO and Board Practice at Spencer Stewart. Jason leads Executive Search and Board Advisory for one of the world's premier leadership consulting firms. He's completed over 250 CEO and Board Transitions.across companies ranging from early stage ventures to multi-billion dollar enterprises. His expertise spans CEO succession planning, board effectiveness, and leadership transitions, particularly for founder led technology companies. Before Spencer Stewart, Jason was an associate principal at McKinsey and a program manager at Microsoft.He holds an MBA from Stanford's Graduate School of Business and serves as chairman of the board for Island Wood. His thought leadership appears regularly in the Harvard Business Review, including a recent article, How CEOs Build Confidence in Their Leadership. What makes Jason's perspective uniquely valuable is his vantage point. He's interviewed thousands of sales leaders and observes whatseparates those who successfully transitioned to CEO and board roles from those who just can't get there. Today we'll explore four critical themes. The sales leaders evolution from operator to strategic executive. Founder transitions building a leadership capacity beyond the go-to-market motion. Board governance for sales leaders. Why thinking like an investor makes you better at your job.and landing your next role, what really matters at the senior executive level. So I guess a couple of things there. You really don't work hard enough or really haven't accomplished most in your life Mano man, Jason, what an amazing career you've had already.And I'm sure you're not going to be slowing down anytime soon. So thank you. Thank you for joining us and joining us here on Selling the Cloud podcast.Jason Baumgarten (02:40)Well, thanks for having me. And I felt a little tired listening to it, but it was all fun in the moment and delighted to try and share some learnings from the many, many, interviews and board discussions and CEO discussions with your listeners.Mark Petruzzi (02:53)Yeah, and Jason, we have an audience of mainly CROs, some of the best in the business. And, you know, there's a number of them that I've already prepped to make sure that they've watched this because they're looking at the things that you do. ⁓ And I have many CRO friends who join us as well that have made this transition. So I love the, I love where we're going here and excited.to dive in. Topic one, the sales leaders evolution. How do you evolve from somebody who's great at sales to configure out management and understand leadership, and then they really have to move to the next level as a strategic executive, often without the background, not to say an MBA or a more prominent type of... ⁓educational background gives you all the recipe to do it as well, but many of them, you know, just they feel like they don't have that. So in your interviewing of thousands of sales leaders, what fundamentally distinguishes those who you feel can successfully transition to the CEO role or to board roles from those who just you feel maybe we'll struggle with that?Jason Baumgarten (04:04)Yeah, it's a great question, Mark. I mean, first of all, it sounds perhaps silly, but I start with do they really want it right? And the reality is not everyone really wants to be a CEO once they learn what that role is all about. ⁓ And so you have to start with not wanting it for ego reasons or control reason, but really do I want to do that job more than the job I'm doing today? So that's sort of step one. It's important. A of people breeze right through it, but I'm like, no, actually, do you really want it? And why do you havethought out reason why. The second thing is, you know, sales, ultimately, I think have a sales leaders have a couple of critical advantages. One great sales leaders have real industry and customer intimacy, and great organizations are built around solving customer needs. And so if you can really lean into that proximity, that superpower, that's super helpful. The second is most sales leaders are great people leaders.And so if you're really thoughtful about how do you lead a team? How do you lead people? That's another thing to lean in. What are the areas they tend to be less good at? Well, the first is genuine curiosity, right? One of the challenges with sales is one can become quite transactional. How do I hit my number? How do I move the sale along? How do I move the conversation along? How do I get what I want done, done? And the reality is great leaders are deeply curious. They're deeplyinterested in learning about other functions, other aspects of the company. So the first thing I'd say is tap into your innate curiosity to learn about what's going on in finance, what's going on in legal, what's going on in product, what's going on in marketing, what's going on in customer success. So that as you evolve your thinking, you understand more about what's happening in other functions. The third thing is actually rising up.and doing two things. First, think as a systems thinker about how do all the pieces of the puzzle fit together to make revenue and profit happen and get knowledgeable about that system. And then two, ensure that you are not coming across as somebody who believes sales is the answer or the cause of all problems or solutions. So those are a few of the things that I'd share. We can go into more depth on any of them.But there's some of the high-level things if I had to add a final one, I'd say humility I always laughed that if I interview all the top sales leaders at a company that revenue will beat will go up at least a thousand percent from the interviews alone when you just add up all the numbers and of it is there's an amazing quality of confidence and You know that a lot of sales leaders have but recognize that when you're interviewing for a CEO role or for something else you've you've got to temper that a little bit withMark Petruzzi (06:24)Yeah.Jason Baumgarten (06:40)that empathy, that curiosity, that humility.Mark Petruzzi (06:42)KK, I think you're on mute.KK Anderson (06:43)Well, that's a first for a podcast to land. Jason, really interesting what you're saying. And you've said that board members can sometimes be like Christmas lights. Like, you know, they turn on once a year, right? And so for a CRO walking into, you know, a board meeting, like, and thinking about how, how...Mark Petruzzi (06:46)Yeah.Jason Baumgarten (06:46)Yeah.KK Anderson (07:05)What advice do you give? Maybe they're not aiming to be CEO, but what advice do you give them around not just being seen as a salesperson? Talk to me about that. Talk to me about a CRO walking intoJason Baumgarten (07:15)Sure. Youknow, first and foremost, it's think about your stakeholders and most salespeople do this really well. So think about who's around the board and what matters to them. What are they thinking about? What's their what did they show up worried about or excited about in that board meeting? And I don't mean conceptually and for all time Memorial, but like in that meeting, what's on their mind? What's going on in their companies? What's going on in their investment groups? If it's a public company, what's going on in their day jobs or their other boards?What is the context? know, are you, are they walking into a new product launch being announced at your company? Are they walking into a bad quarter? So the more you start with who am I presenting to, who are these people on the other side, not just in the singular dimension of them as your board member or investor, but also the rest of their lives. So that's sort of step one. Step two is to your question of how do you appear as more, you know, how do you present a more holistic perspective? You know, I thinkIt really comes from that ability to connect the dots between what's going on with your customers and the market, you know, competitive point of view, you know, customers need shifting product evolution, technology evolution. So that's one. And then the other is being able to connect the dots inside the company. You know, we did this thing on, ⁓ our customer support initiative. It had this impact on renewals. This then led us to be able to change the way we're going after new logo.The more you can stitch together narratives that are multidisciplinary, the more they start to see you as not a one-trick ⁓ answer. And the other thing I'd say is know when the answer is not sales. One of the most powerful things any functional leader can do is to say, that's a great question. I actually think the answer is in marketing or is in HR or is in finance or is in customer support.You could give us more resources and sales, but that would be the worst place to put the capital to solve that problem. Because showing that shows that you are stepping out of your functional role to really think about what's best for the company and how you as a systems thinker would apply that capital or that resource.Mark Petruzzi (09:15)Jason, so in general, when should a CRO start thinking about building the capabilities beyond the pure sales, execution, sales leadership side? What's the signal?Jason Baumgarten (09:27)So I think there's two things that are working in tandem. One is their ambition, right? Do they have ambition to do more bigger, more complex, even sales roles or CRO roles that are broader than sales? And then have they mastered where they are? So at a very simplistic level, do they feel like they've kind of got the, you know, the training wheels off in their current role? You know, do they have sales ops team leadership, you know, forecastingKK Anderson (09:37)it in thatJason Baumgarten (09:49)all those key skills down, if they do, it's a perfect time to now start to think about how do I broaden? If you haven't got those mastered, you know, probably need to spend time there. But if you feel like you've got your quote unquote day job in good order, it's only going to make you better in your day job. And that's I think one of the things people often forget is they think, I'm doing this to become a CEO or to become a board member, or to take on more, it will actually make you much better in your day job.because you'll start to think about ⁓ other levers you can pull with your colleagues to help move revenue beyond what's in your control. And that influence in your leadership team, you will be more effective because you won't be seen as somebody lobbying for your team's resources, but for solving, know, every function wants more revenue, more profit. So when you start solving for that, you become an enlightened sales leader who,everybody wants to pull into their opportunities, their, you know, their initiatives, et cetera.KK Anderson (10:46)Isn't that the truth? Yeah. Jason, let's move on to the second topic and talk a little bit about founder transitions and building, as you've been discussing, that leadership capacity beyond just the go-to-market motion. And you have worked with many famous founders, ⁓ and you've had the ability to see a lot of these founder-led companies up close. And so I would love to hearyou know, maybe a story or two about some of your, your favorite famous founders that you've led. and then specifically like when, when they stopped becoming the primary salesperson, right. And the company starts to scale. I'm curious, like what usually breaks first, right. And just talk, talk us a little bit about some of your, favorite famous founders.Jason Baumgarten (11:30)So I think I've worked with almost all of them in some form or fashion. ⁓ You know, I would say that what tends to break is sleep. If I'm realistic, it's, it's the thing is you just only, no matter how amazing somebody is, they only have so many hours in the day. And so that's one. I think the other thing is that, you know, and you know, this as well as everybody ⁓ who really is an expert in sales, the one-on-one connection of an individual can only scale to so many people.KK Anderson (11:36)Okay, there we go.Jason Baumgarten (11:54)And so I think what starts to happen is that while they typically are doing more of a business development motion, more than a real scaled sales motion, they start to realize, I need some channel sales. need some indirect sales. need some marketing driven conversion. I need more tools in the basket. And then they start to build a sales team beyond them. Now, I think the early sales leaders of many companiesare individual contributors themselves. And so there's almost two evolutions. There is the first, you know, it's the founder being the salesperson, and then there's the first salesperson being the only salesperson. And then it's you as a sales leader kind of going to the next level as a ⁓ building a team, building a, you know, a model of sales. So I think that's often the trajectory these companies go through. I would say the other watch out isMark Petruzzi (12:28)ThankJason Baumgarten (12:42)founders who have a couple of really good early deals and think, boy, this sales thing is easy. And then they start to scale it. And they realize that that was just friends and family. And people thought it was great. Or they got some early pilots and it's not easily replicable. And so I think when you really ⁓ move from founder stage to a growth stage is when you can replicate that journey, when you know that you can hand this to someone else and Mark can go sell.just as well as I can. Founders are always going to have a special edge, right? The reality is if a founder calls a company, they're always going to have a little extra time. It's a little easier to get through to an executive, but until you can replicate it, you really don't have a repeatable sales process. ⁓ You know, I would also say that what we're seeing now is a real evolution in how people are thinking about it, because you are also seeing ⁓ much more complex sales motions.And in some cases that's complex because we're seeing them look more like consumer sales motions. And in some cases, much more like consulting or professional services. So we're seeing more bifurcation than for a while we were into the fairly low complexity SaaS sale, you know, and that is on the edges starting to fray a little bit in terms of just the complexity of, the heterogeneity of all the different types of products and services we're seeing in technology.So maybe avoiding a particular person, but, you know, I think everybody goes through that wave and, you know, I worked with one leader who his startup was in the sales technology space. And that was perhaps the most incredible cause he was one of the best salespeople period. And he was one of the best salespeople for that company, even when they were at, you know, several hundred million dollars in revenue. But he realized he had other things he had to do. And if he spent all his time selling,So what he started doing was spending more time teaching and making sure the right process was in place to scale as opposed to saying, I could do that better. Because of course, but he also couldn't do everything. had to, he had to pick what he was spending his time on.KK Anderson (14:38)Especially if he wanted to sleep, right?Mark Petruzzi (14:40)Now that Jason, that is spot on. So in some of your publications, articles that I've read, you mentioned two critical dimensions. Building the right go-to-market engine as one aspect of it. And then at the same time, readying the organization for when it's not founder led sales anymore. And they're not spending 50, 70 % of their time on sales.How should boards in particular approach these transitions? What responsibilities do they have in all of this?Jason Baumgarten (15:13)Yeah, it's a great question. It does depend on this on the type of board and this, even for startups, what's the type of startup and the ambition of the startup? You know, I think the thing that boards should spend the most time on is what is the theory of the sale? Like what is the theory of the sales system that the company is starting to move towards when it goes from an individual to a system? Second, based on the data, you know, the early returns early data,is that hypothesis or theory holding true, right? So for example, if we say, we're going to sell into this ⁓ type of executive, we believe it's get a demo, show the demo, do a pilot, you know, whatever the the march you're taking people through, is that actually proving out in the early data? And then the third thing is, is the company continuing to appropriately experiment and test whether they have the right model? Because I think it's probably the mostdangerous thing is to very early and we see this when an executive comes in and says well I've heard it I know the way to sell is XYZ and I'm gonna bring that into this startup and it isn't the right model right something is off either the ideal customer profile is off or the literal ⁓ you know Approach is off or the pricing is a little bit off Something in there is a little off and instead of catching it early. They catch it really late That's really bad for that sales leader, but it's also really bad for thisfor the company. so board members can really try to make sure there's a crisp hypothesis as to here is how we're going to sell. Here is the data that's going to show us that we've got the right model. And then three, are we seeing reinforcement that we picked well, or lessons learned that maybe we've got something off and what are we doing to adjust. ⁓ And then you can start to diagnose what's going on if you're not hitting or beating your expectations, you can say, we had something wrong. And that's okay. I thinkThe worst thing is to double down and say, we just aren't trying hard enough. It usually is a strategy or a process problem, ⁓ not a try harder problem. You know, unless people are just flat out lying about what they're doing, but I don't find in, especially in startups, people are usually pretty excited to grow the company. And so they're showing up, you know, trying to kill it. The other thing is not recognizing that whatever works early is probably not the forever model. AndFor example, there was years ago, an enormous number of SAS companies that had very low cost direct models. And they realized that that wasn't going to scale that they needed to get a more enterprise motion. And yet they built teams that were so well oiled for a particular model that when the when the growth rates started to slow down, they didn't they weren't as quick to transition or try new things. And that's a failure. The know, it's a failure of the leadership team. Buteven a failure of the board because the board should have been asking those questions earlier than the executive team because the board's role is to try and look ahead of where the executive team is is reacting to right now because the executive team might be You know 70 % reactive 30 % planning the board should be the other way around and should be able to say hey I think this is going to come and hit you in a year or two years. How are you prepping for it? Now? What are you doing now? How are you learning now? So that's how I think about that board interaction early onKK Anderson (18:14)You know, we were just interviewing Mark Roberge this morning on the release of his upcoming book, The Science of Scaling. And he was talking a lot about, you know, an early, you know, indicator of retention around, you know, customer success. And so for a sales leader, you know, they are a CEO might be thinking like, hey, just get us more leads, you know.get it, we just need more pipeline. Pipeline will fix everything, especially in these early stage companies. And Mark's argument was actually, what you really should be focusing on is your retention. Like, are you hitting those benchmarks that show that people, your customers are staying and you have, you know, product market fit, you have go-to-market fit, your customers are there and they're coming back and they're renewing. So, you know, talk to me a little bit about kind of your perspective onon that idea and what are some, like when you see founders, you know, start to show maybe a lack of leadership or like you're like, I want to coach them to increase their acumen as their companies grow and scale. And you need to take into consideration things like, you know, the retention metrics, you know, more so than the sales metrics. And you said earlier, recognizing that sales isn't always the problem.Like what does all of that make you think of? what's your perspective there?Jason Baumgarten (19:24)Yeah.I mean, first of all, I think he's spot on and I'd go so far say, you know, you want your metrics across the whole consumer lifecycle, you know, the whole client customer lifecycle, because it may be showing up in retention, it may be showing up in a lack of cross sell, it may be showing up in different areas. And the point is not to say we did a good or bad job, let's understand what's going on. It may be that you're got great conversion, but with all the wrong clients. And the real issue is you're going after the wrong clients, the wrong customers.not ⁓ that you are incapable of turning those leads into opportunities. So I think the first thing is I'm a big believer in capture the data across the whole life cycle so that you can understand what's going on with the sales approach, you know, depending on the type of product we're talking about, the, you know, the onboarding, the services side, the customer support side, et cetera. So I think that whole life cycle is critical. I think that when, ⁓You know, when founders are finding themselves stuck, usually the answer is go talk to people who have done who are a little further along in the journey than you are and ask them for advice and counsel about what worked for them. And don't take one person's advice. Don't say, well, you know, one investor told me the answer is this metric. So I'm going to go chase that metric, triangulate different people, get a good kitchen cabinet together.and ask different people and don't just ask peers, don't ask other founders alone, don't ask other CEOs, ask people who are in CRO roles, ask people who are individual salespeople, ask people who are in other parts of the ecosystem so that you're hearing perspectives from, you know, the person who might be junior entitled to you, but much higher than you in scale. You know, I always laugh, you can be CEO of your own business, just pop a magnetic sign on your truck and drive around and Mark's got Mark and Co.He's a CEO done. You don't, you don't need to actually have a company to be CEO. Same thing with the sales person, right? If you're selling lemonade, you're a sales person. But if you're, you know, you could be a very junior person selling millions of dollars in a very complex way for an enterprise SaaS company, or you could be a founder who's got a big title and a lot of sense of importance, but you're selling half a million dollars. And that doesn't make you more sophisticated as a sales strategist and the person who's aMark Petruzzi (21:09)Mm-hmm.Jason Baumgarten (21:36)senior manager at a big SaaS company. So don't just think about your peers. Think about, you talking to people in different roles and different scope and scale? And to me, that helps you understand what's going on. It also gives you empathy because when you start thinking about things like incentive plans or how to inspire the team, you also are thinking about, wow, how does that work when you've got 40,000 people?I've got five, how does it work at 40,000? So I think the more they can get out of their own atmosphere, it helps a lot.Mark Petruzzi (22:08)So Jason, I'd like to take you back to the board perspective for one more question here. So what mistakes do boards typically make in the timing and structure of hiring professional sales leadership as they move from a founder led selling motion?Jason Baumgarten (22:26)Well, I think that I think the two biggest mistakes I've seen is they don't do it early enough. Right. There's a sweet spot. If you do it too early, you don't, you don't have product market fit. There's no point in bring on your professional sales leader. If you wait too long, things get pretty calcified before somebody has a chance to think about your incentive design, your partner design, your channel design, all those things. I would say the other piece of the puzzle is hiring somebody who is going to bring theAnd if you don't, you know, you can either start with a very open mind, you know, classic beginner's mind and say, I don't know what model, but I'm going to use this recruitment to help figure that out. Or you can do the work to say, we've actually figured it out. I figured it out or your team has figured out. And we now know what kind of sales leader you need, because if you believe your PLG and you're really not, you can hire the absolute wrong person. And that's not good for anybody. And I'm a big believer that there's, there'sthere's not good and bad sales leaders. There's not good and bad leaders is actually people who are the right fit for the right time. And so you need to make sure that the fit of that sales leader is what you need. ⁓ The third thing I'd say is sometimes they just over, ⁓ you know, there's a desire to sometimes signal a Rolodex and get somebody who's got a big Rolodex. And maybe because I'm in the Rolodex business, I always laugh. like, listen, if you've got a product that's solving real problems,getting access and the Rolodex will be the least complicated thing. And people want problems solved. And so if you really have a good solution, you will find a way to those people. That is probably the least value in most industries. That's probably the thing I would not get hung up on early. And yet I think a lot of founders think that's the magic unlock. The reality is most human beings at best,best have 100 to 150 relationships. And that's actually overstating the real quality of most of those relationships are ⁓ not preferential. Meaning if you and I have the same product and we both go, I'm not going to win it just because I have that relationship. It's really going to come down to who is the better product. And so I would say don't over bias to that concept of access.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Cherilynn Castleman, enterprise sales leader turned strategic coach and Harvard instructor, joins Mark Petruzzi and KK Anderson to break down what AI fluency really means for modern sales teams.Rather than treating AI as a shortcut or replacement, Cherilynn reframes it as an amplifier of human strengths like perspective, empathy, and trust. She shares practical, Monday-ready routines that help sellers show up with stronger points of view, deeper buyer relevance, and clearer deal strategy.This conversation also dives into the science of trust in a noisy, AI-saturated world. Cherilynn explains how the questions we ask and how we listen directly influence buyer confidence, especially inside complex buying committees. From discovery to prospecting to executive conversations, this episode focuses on how sellers and leaders can create credibility without adding more noise.What You’ll Learn:AI as a Daily Sales Discipline: How a simple 15 minute daily AI prep routine helps sellers develop POVs, anticipate change, and continuously improve.POV Development at Scale: A repeatable framework for triangulating industry, company, and persona insights using AI.Making AI Revenue Relevant: Why leaders should evaluate AI through insights, context, and business impact instead of activity metrics.Trust in the Age of AI Noise: How better questions and deeper listening create credibility when buyers are overwhelmed with automation.High Connection Discovery Questions: How to use AI to reframe discovery questions that trigger trust, openness, and buyer engagement.Prospecting Without Pitching: Why offering value through insights, case studies, and tools beats asking for meetings.Navigating Modern Buying Groups: How to adapt when new stakeholders like CFOs enter late-stage conversations.Financial Fluency for Sellers: Why precise numbers, not rounded estimates, matter when speaking with executive buyers.Key Topics:AI fluency as a mindset, not a toolsetDaily AI routines for sellers and managersPOV creation using LinkedIn profiles, 10Ks, and industry analysisRelationship selling and the science of trustDiscovery questions that increase buyer confidenceAvoiding buyer defensiveness and ethical AI useExecutive conversations and CFO expectationsFinancial storytelling with insight, context, and impactGuest Spotlight: Cherilynn CastlemanCherilynn Castleman is an enterprise sales leader, strategic coach, and Harvard instructor focused on helping sellers become trusted advisors through AI fluency and relationship-driven selling. She is the creator of highly rated AI and sales programs available on Udemy Business and leads large learning communities through weekly live sessions and workshops.Cherilynn is on a mission to equip one million women in sales and leadership with the confidence, fluency, and playbooks needed to thrive in modern go-to-market roles.Resources & Mentions:Course: Smart Tips Sales – Master Relationship Driven Selling via AIBook: Post-Pandemic SellingResearch Reference: Dr. Jane Dutton on High Quality ConnectionsConcepts: AI fluency, POV selling, high connection discovery, financial storytelling🎧 Listen now and follow Selling the Cloud for more insights on modern sales leadership, AI-driven GTM strategy, and building trust at scale.Mark (00:31)to Selling the Cloud. Our guest today is Cheryl Lynn Castleman, an enterprise sales leader turned strategic coach and Harvard instructor as well. She helps teams become trusted advisors with practical AI fluency and relationship skills. She also builds accessible learning at scale as a new to me creator. Her course, Smart Tips, Sales,Master Relationships Driven Selling Via AI is super highly rated and available versus a via Udemy business. Her programs focus on outcomes you can see on Monday morning. Better discovery, cleaner deal strategy, clear next steps. She has coached thousands of sellers and leaders, lifted promotion rates through hands-on coaching.and built a large learning community through weekly live sessions and workshops. She teaches simple operating rhythms that free time for customer conversations rather than adding more dashboards. And she's on a mission to equip 1 million women in sales and leadership with the fluency, confidence and playbooks to thrive. Here are three topics we'll cover today. AI fluency as a daily mindset.How to use AI to amplify strengths and turn prep into a repeatable routine that shows up every day in results. Relationship selling and the science of trust, the questions and behaviors that build credibility fast with modern buying groups, and leading as a CRO in a time of extremely rapid change. How to focus to team, communicate change, improve impact without adding any additional noise.Sherlyn, we're so happy and proud to have you here. Welcome to Selling the Cloud.Cherilynn Castleman (02:13)Thank you, Mark. Thanks, KK. I'm thrilled to be here today.Mark (02:16)All right, we're gonna take you right into our first topic. And our first question is, you frame AI as an amplifier for what sellers already do well. If a CRO asks you to install AI fluency in 30 days, what would reps and managers need to do each day and each week? And what early results would you expect by say week four?Cherilynn Castleman (02:38)So first of all, I would start with a 15-minute AI prep session for every rep. I would have them spend 15 minutes asking AI, first of all, one, to develop a POV, a point of view, which I know we're going to talk about a little bit later, for each of their clients. It's something they can do very quickly to triangulate and develop their opinion, because as you know, state of sales reports from LinkedIn and Salesforce told us that 87 percent ofB2B buyers expect us to show up as trusted advisors, meaning we have to have a POV. So use AI to develop your POV. Second of all, spend five minutes using it to look around the corner. Where is my industry going? Where is my product going? Where is my company going? If you ask those questions every morning, you're going to get insights. And the final thing is, what can I do better? What can I, what am I missing? How can I, so for example, I'll say,How can I be a better coach? How can I connect better with my audience? What is a new training insight I can try? What's a new engagement I can use on Zoom? I am every day getting better. They spend 15 minutes every day amplifying what they already do. They're going to accelerate deals. Number two, I would encourage managers to add to their weekly minutes, teach me something in five minutes. Have every rep teach something to the rest of the team.once a week. That means by the end of four weeks your team has learned five AI insights. Over the course of a year they will learn 50 AI insights. And I had a client who was in the middle of the pack as a manager for a Fortune 100 fintech company and she became the number one sales manager of the year within six months just by doing that one exercise. That will free upAnd what you will see is you will see about 30 minutes a day freed up from your reps. That 30 minutes, if you have 50 reps and they're doing about $100,000 per deal and they're doing one deal a month, if you take that math out, that will give you an additional $4.5 million in new revenue that and no additional headcount.KK Anderson (04:44)Wow, it's really fascinating when you put it that way and you break it into numbers.Cherilynn Castleman (04:47)Yeah, and that is one of the biggest takeaways, I think, that sales leaders and chief revenue officers can look at is when we first started using AI, people were talking about how to use it for email and how to ⁓ sound better. And what the most recent research is coming out is you have to ⁓ apply what I call ICB, insights, context, business impact. How is it driving revenue?How is it saving you money? How is it increasing operational efficiency? How is it increasing your ROI? Those are the questions that leaders want to start asking every single week. This is what my reps are doing. How is that making me money, making me more money, or saving meKK Anderson (05:28)And it's interesting because you need the leaders, the L1s and the L2s asking AI those questions and using the data to get smarter. But the sellers as well, like you said, use it to look around the corner, research your competition, your customers. And we know and have known for a long time that our customers are much smarter when they get to us. They know more about our product than we probably do.Cherilynn Castleman (05:48)It used to be there were a ⁓ couple of months ago we had about 79 % usage today. B2B sellers are 98 % using AI. Customers are 100 % using AI. So your customers are using AI and 100 % they know your company, they know your competitors, they know your product. They probably have done more research than you have. So that's why you have to show up.Mark (06:02)ThankCherilynn Castleman (06:12)with a POV, you have to connect with them, you have to build trust with them. People want to do business with people they know, like, and respect. Period. And we can leverage AI to do that.KK Anderson (06:24)And so where I was gonna go next was, I actually, I kind of thought people were getting over this idea that AI is cheating until I was in the car with my kids of all people. And one of my daughter's friends was like, AI is cheating, I can't believe AI, it's just not fair. And it's interesting, do you hear that still in your trainings and your classes that people feel like it's a cheat?Cherilynn Castleman (06:47)And with a lot of women, Harvard did it. There was an article that was recently said how AI is impacting women's career. And they discovered that women use AI in business 10 to 40 % less than men. And when they asked them what was the real reason, women said, because it's cheating. And so I tell people, just reframe it. I said, take what you already do well.What is your superpower? What is the one thing that you're better at that AI will never replace? AI will never replace your authenticity, your ability to care, ⁓ your ability to connect with people and ask AI to help you elevate that, to amplify that. Take 15 minutes in the morning and say, I'm a great listener. How can I be better?I ask great discovery questions. How can I do better? I'm meeting with this client. We don't seem to connect. How can I connect better with this type of client? My client's very analytical, very amiable, very expressive. A trick that I tell people is write a simple email and then ask AI, rewrite this for an analytic, rewrite this for an expressive, rewrite this for a driver, and rewrite this for an amiable. They're different as night and day. That alone will help you connect.with your clients, just reframing that. Another example is if you go to LinkedIn, go to the three dots, and it says PDF this profile. PDF the profile, attach it to the AI tool that you're using, and say reframe this email specifically for this person. And it will say, they're very innovative. They're very amiable. They're very analytical. And it will reframe it. You will connect with them. That's the power of AI and connecting with people.Mark (08:24)All right, well, that's very cool. So please help us to make this a little more Monday ready. Let's say a rep has a discovery call this afternoon with a new account. Walk through the 15-minute AI assisted prep that produces in your mind the most useful point of view for the call and how you coach them. How do you coach them to bring that into the conversation? We've discussed a little bitthis here, but take us a little deeper if you would.Cherilynn Castleman (08:51)Absolutely. So what I always coach my clients to do is to triangulate your POV. It's something that AI, generative AI tool does so well. So first of all, research your client. Pull down their LinkedIn profile. If they're an executive, pull their bio and that's number one. So you want to triangulate. want three things, industry, company, person or persona. So if you can't find the person, do a persona.Pull down several CFOs in that industry. Pull down, if they're a Gen Z, pull down Gen Zs in that industry in that job role. So the better you can micro-segment, if you can't do the person, do the persona. That's number one. Number two is company. My favorite company document for publicly traded companies is a 10K. The Form 10K, as your listeners know, I'm sure, comes from the Security Exchange Commission. You can get it onthe investors page of any publicly traded company, and the third one is an industry analysis. My favorite place to get it is Value Line. Value Line is free on every public library. If you work for a large enterprise company, they have this information for you. They have an industry analysis. They have company analysis. Pull it in and ask AI to triangulate this for you.and it will pull the three together and develop a POV. And then you just say to somebody, Mark, if I said to you, I have an idea I want to run by you, what would you say? People say, yeah, nobody's going say no to an idea. And that's all it is is an idea. Even if you're wrong, you get credibility because you showed up with an idea. So show up with an idea. This takes 15 minutes. This used to be an eight-hour workshop that I did on howMark (10:15)Yeah.Cherilynn Castleman (10:31)to research and how to read a 10K. Value Line has the ratios in there, so it can pull it and it has the ratios in there for three years. It will do a financial analysis POV, it will do an expressive one, any way that you want it. Fifteen minutes.KK Anderson (10:46)And then you take that information and you turn it into a value hypothesis for what outcomes your customer wants to achieve and what's going to get in the way and how you can help.Cherilynn Castleman (10:54)Yes.Right. So if it's a first interview, those are the three things. If it's a second interview, I include the discovery document with it. And whether you are going into a meeting and saying, have an idea to run by you, and you're starting your meeting that way, or you're sending a follow-up email, or you're going into your solutioning, or you're doing a demo, it doesn't matter. You always want to show up with your opinion. I'm the trusted advisor. I have an opinion.And that's what it is. And you could say, how does this land with you? Or this is what I'm discovering in the industry. How does this resonate with you? You're asking their opinion, but you're showing up with somewhere to start other than just with open-ended questions.KK Anderson (11:35)So let's, we could stay on this topic forever. Let's move on to the second topic though, relationship selling and the science of trust. And what's interesting is I was listening to a podcast just this morning about how, thanks to AI, right? And if you, I mean, you see it every day, you scroll LinkedIn and it's like emojis and dashes and it's just a bunch of chatty-bitty trash, noise. Let's call it noise. I wouldn't say all of it is trash, right?And so, and people are used to seeing that now. And so it's like the trust continuum is getting longer than it used to be. Like it used to be, like if you had a really slick website, you know somebody dropped 10 grand to build a really slick website or way more than that, right? You you used to be, and now an AI tool can turn that on and you know, 30 seconds flat. And so it's harder for people out there to know who they can trust and what's real and what's not real. And so,you teach that trust shows up in what we ask and in how we listen. you know, AI is making that harder. Like how, like, how do you balance that? Like how have you added that whole dynamic and that change into your teachings and your coaching?Cherilynn Castleman (12:41)So the first thing that I do is I ask my clients to pause for a second and tell me what is it about their client that they really care about. You have to give a damn about your client. There's no AI tool out there that's ever going to do that. And that's where you start. So if you really care about your client and you pause and say, what is it you care about? What is it that's important to them? And if you don't know, that's the first place you start, because that's what you have to start from.is you have to care about your client and what's important to them. Once you care about them, you can craft discovery questions that are high connection questions. And for example, and AI can help you do this. again, it's a tool to amplify and elevate you. So Dr. Jane Dutton at the University of Michigan has done a lot of research on high quality connections, HCQ. If you go in and ask AI,to reframe your discovery questions as high quality connection questions, what you're gonna do is you're gonna trigger what I like to call the love hormones. It is the oxytocin. It triggers the hormones that makes clients trust you, like you, want to do business with you. For example, I had a client who was in the financial services industry.And she used to ask her clients, tell me about your insurance policies or your insurance that you have. you how you feel when somebody asks you that. Her second appointment rate was around 17%. When she asked AI to refrain that, the question was, what is it about insurance that scares you? Can you see that just that little switch there makes somebody connect with you? I have another client, she's a career coach, and she used to say, tell me where you want to be in three to five years.And she was coaching women and AI suggested that she ask, when was the last time you cried at work? Because if you're a woman and you're going to look for a coach, it's probably because something is upsetting you to tears. And so you can ask little questions that just connect with people. have a client that she sells ⁓ data to, she sells data andAll of her clients are data scientists. And she said, Sherrilyn, data scientists don't have feelings. I can't ask you questions. And I said, hear me. Just for one week, let's just try it. She came back, and her clients now know her as a data therapist. Because she started asking them, what does it feel like when your company asks you to change the algorithm real quickly to come up with something? And this frustrates and angers, and they don't have the right data. And so her solution helps.resolve this and she's like now all my clients want to start with how they feel every time we meet. So she connects with them. She was able to renew more accounts than she ever has just by starting asking those types of questions. ask better discovery questions. Two of my favorite ones are either first or finance. What was it like for your first podcast, KK? Can you remember your very first podcast?KK Anderson (15:38)Yeah, the instant emotions, instantCherilynn Castleman (15:39)Okay,you see the emotion, you see what happens? Versus telling me about what's it like to have a podcast as a first question. Or if I asked you, Mark, what was your finest podcast? So first and finest questions are great connections to connect with people. You can make these very technical, very financial, very industry specific, but an AI can help you do that.KK Anderson (16:01)And I know Mark's gonna jump in here, but I gotta ask one more question. That's brilliant, by the way. I absolutely love that, first and finest. What about in prospecting, when you're trying to get the meeting? How are you breaking through the AI noise and building trust?Cherilynn Castleman (16:15)So just bottom line, offer value, offer value. Offer case studies, offer assessments, offer checklists. People are doing research. People want knowledge. And so I say leverage social proof. AI, anybody can go out in AI and say, I am a great coach, or I am a great podcaster, or I'm a great ⁓ strategist. Use.LinkedIn or whatever platform you use or emails or whatever, however you're doing your outbound to demonstrate that you can prove you do this. So offer social proof. Here's a case study where I helped a client like you do this. Here's a checklist that I use with my clients. Here's an assessment that you and your team might want to take. I have an AI assessment tool that I give out and I'm constantly saying, do you want to see where your team is for AI fluency? Take this AI fluency assessment. It is just a free tool.Here's a handout on how to prompt like a pro. Give value. Once you give the value, then I always say, if you have more questions about this, jump on my calendar. People know how to book meetings today. You don't have to book them. You can wake up every day with new clients on your calendar by offering value and insights. I ended up with ⁓ a huge client from a major retailer who said,KK Anderson (17:19)Yeah.Cherilynn Castleman (17:27)She just, she used all my free resources for six months and finally she's like, okay, now we gotta bring Sherrilyn in.And she just got on my calendar, so we want to hire you. It's just that quickly. so what it is. The trust is there. Here, give value, give value. Stop saying, hi, I read your post and let's have a meeting. never, don't ask for meetings. Just give value. And again, if you can't think of what to give away, AI can help you come up with tools, resources. You have case studies. I've got clients who've gotten job offers.and ended up earning six figures more than they ever had just by posting case studies on LinkedIn. Here's what I did with a client anonymously. Here's what I did with the top 10 airline. Here's how I helped them and the percentage I helped them did the case study. And I had a woman, the chief revenue officer called her and said, I want you to come in and be my head of sales ⁓ and went around HR and didn't even look at a resume. It's like, whatever you did with that client, I want you to do that for us.Because it's proof, it's a social proof, a lot helps you do that.Mark (18:29)Right on. Sherilyn, that's so you've taken us through some of the things that you want to say and things that add value to the full discussion early on. Let's talk a little bit about things that that you want to make sure you don't say or things that could actually trigger things like buyer defensiveness. And in general, like what two behaviors that do you see thatyou know, that you can then do the lower that threat and increase that openness right away.Cherilynn Castleman (19:01)So one of things that I call is don't be cringy, okay? There's so much information out there. It is so easy to take someone's information and abuse it. Don't do that. Just treat people the way you want to be treated. So number one is don't be cringy. Don't take the data, don't share somebody's information. Be respectful, be kind if given a choice betweenYou know, right and kind, choose kindness, just always be kind. I always say a fool with a tool is still a fool. There are fools out there with AI. Just because you have AI doesn't mean that you have to abuse it. Be ethical, stop and think about does this make sense? Is this ethical? The other thing is you will know if you're not triggering the trust and the love hormones, you're triggering their amygdala. And what happens when you trigger their amygdalais you see fight, flight, fawn, or freeze. If you're seeing any of those with your clients, they're fighting with you, they're arguing with you, they are freezing, they are not showing up, they are stalled, they are fawning. You ever ask a client a question and they sit there and they look at you? Well, they are fawning. just, you know, that's where they are. Or they just ghost you. Any of those say, okay, I've done this, it's time to stop, and AI is a great tool. I tell people,open a Word document, dictate just in your own voice what happened and ask AI to help you analyze it and say, what did I do wrong? What could I have done better? What made my client freeze? And learn from it. Another thing I see is that you mentioned it. So people try to sound ⁓ more intelligent or more technical. And how do you feel when you're around people with pretense? How do you feel when you go to that Thanksgiving or holiday mealand your in-laws or somebody has a girlfriend or boyfriend with them and they're just putting on airs. Everybody knows it. They can't stand it. Well, we don't want to do business with people like that. So the best way to be authentic and have your authentic voice come through is to just dictate. I use Word because it's not intimidating. I tell people just go into Word, hit the dictate and just dictate the email. Dictate the script. Dictate what you want to do and then drop it in. AI will use your words.they will use your intonations and you will sound like who you are. So those are a couple ways to avoid triggering the amygdala and have somebody go into fight flight freezer form for you.KK Anderson (21:27)I'm a big follower of Rory Vadin. I don't know if you know him. He runs Brand Builders Group and he wrote the book, Take the Stairs. And he says, my gosh, I feel like I've been quoting this every day. He says that in today's age, your humanness is now your uniqueness because everything else is,Cherilynn Castleman (21:34)Okay?KK Anderson (21:46)AI generated, like you have to leverage your humanness as your uniqueness. That's, that authenticity is still, is now even more than ever, you know, paramount. So buying groups are larger, they're complex. Very often, in these times, leaders who used to have decision-making authority now have to get the CFO involved and, and, and they're.Cherilynn Castleman (21:51)Yeah.It is.KK Anderson (22:09)more constrained than they've ever been. And so how are like, on this theme of building trust and authenticity and triggering the love hormones, I love that by the way, how do you do that when you've got like a buying group that's constantly changing? Like you're halfway through your sales process, you're on a, you have a meeting to negotiate or talk about terms of something and then next thing you know, boom, the CFO is there and you've never met him before. Like what are your kind of tips on that?Cherilynn Castleman (22:36)So a couple things. So first of all, I always ask at the beginning of any meeting, whoever's there, because like you said, buying committees are much larger. They used to be three to five people. Today they can be 12 to 18 people on a buying committee. Regardless of how large the buying committee is, at the very beginning, always go into the meeting asking each and every one, if you could get one thing out of this meeting, what do you want out of this meeting? Because...That may change the direction of the meeting. So you don't want to guess where the CFO, the CFO could be there because they're looking for operational efficiency, cost savings. They could be there because they're looking to drive revenue. They could be looking to improve the pipeline. You don't know why they're there. And so ask, and so I always ask, even if there are 15 people in the room, I'll take 15 minutes and say, real quickly, what's one thing you want at this meeting? And I note those down. Now I have the direction of the meeting. That's number one. Number two.Do your homework and do like I said, so do a POV for the chief marketing officer, do a POV for the CFO, do a POV so that you have those. So you're not changing the agenda, you're just changing the lens. And number three, executives want to talk about numbers. Develop your financial fluency. Understand what the key numbers are. Are they interested in what's driving revenue?and be able to tell stories. And the stories, again, is the insight, what is the number, what does this number mean, and where is this number going? How will it impact us in the future? So is it the cost of acquisition? Is it the cost, is it the life, the cost, the client life cost of, you know, of maintaining the lifetime value of that client? So.Know those numbers and be able to speak to them. And one other tip I always tell people when a CFO is in the room, take your numbers out three digits. Never say 50 million. Say 47.2 million. Know your numbers by three digits. CFOs will dismiss you if you round your numbers as a salesperson. So know your numbers. I'm sorry, what? Yeah, if you talk to CFOs, they'll tell you, I hate it when somebody says 15%.KK Anderson (24:33)That's a good tip.So that's a good tip.Cherilynn Castleman (24:42)Because nothing is exactly 15%. It's 14.7 or 15.2. So know your numbers, know them out three digits, know your numbers and tell financial stories with them where you can talk about the insight from the numbers, the context, and what it means to the business. And be able and have a financial point of view in your back pocket so that you're just changing the lens, you're not changing your agenda.Mark (25:07)Well, you know, Cheryl Lynn, that is also it's like speaking with someone who's bilingual and, you know, speaking in the language that they may be struggle with the whole time and maybe touching it for a second. You know, CFOs, are they are bilingual. And one of the items is numbers. It has to be. So that makes a lot of sense.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of Selling the Cloud, Mark Petruzzi and KK Anderson sit down with Mark Roberge, founding CRO at HubSpot and author of The Sales Acceleration Formula, to unpack why most companies scale at the wrong time and with the wrong signals. Mark introduces a stage-specific, data-driven framework for moving from product market fit to go to market fit, and explains why managing to readiness and retention beats chasing top-line revenue alone.Mark breaks down how founders and boards get trapped copying outdated playbooks, why product market fit is often misunderstood, and how to define it through value realization, not just revenue. He also shares a practical approach for finding a leading indicator of retention, then translating unit economics into clear operating KPIs that make scaling repeatable, profitable, and measurable.What You’ll Learn:Why scaling “scientifically” requires managing to readiness and retention, not just revenue growth.The difference between market-message fit and true product market fit.How to define product market fit using retention and value realization.How to build a leading indicator of retention using a simple “P percent do event every T time” framework.Why startups should delay scalable processes until product market fit is proven.What go to market fit actually means and how unit economics define it.How to translate LTV:CAC targets into practical KPIs like quota, close rates, and meeting volume.How to diagnose pipeline problems as readiness issues vs volume issues using conversion patterns across reps.Key Topics:The danger of copying borrowed playbooks from past unicornsReadiness pacing vs hiring based on fundraising timelinesProduct market fit as value creation, not revenue milestonesLeading indicators of retention and early customer success signalsGo to market fit and unit economics as the profitability testTurning unit economics into a repeatable go to market formulaQuick tests for pipeline issues: lead quality vs sales executionWhy small funnel improvements compound faster than single big swingsGuest Spotlight: Mark RobergeMark Roberge is the founding CRO at HubSpot, where he helped scale the company from zero to IPO. He is co-founder and managing partner at Stage 2 Capital, a Harvard Business School senior lecturer focused on sales and go-to-market strategy, and the best-selling author of The Sales Acceleration Formula. His newest book, The Science of Scaling, distills decades of research into a stage-specific roadmap for scaling with measurable readiness.Resources & Mentions:Book: The Science of Scaling (pre-order available)Book: The Sales Acceleration FormulaConcept: Product Market Fit vs Go to Market Fit vs Growth and MoatFramework: “P percent of customers do event every T time”Example: Slack’s activation benchmark (high-volume team messaging)SaaS Metrics: Retention, Leading Indicator of Retention, LTV:CAC, Payback PeriodReference: Winning by Design and compounding funnel improvement🎧 Follow Selling the Cloud for more episodes on building durable GTM systems, improving sales execution, and scaling revenue with confidence.Mark (00:00)Welcome to Selling the Cloud. Our guest today is Mark Roberge, founding CRO at HubSpot, who has helped lead the team from zero to IPO, a beautiful IPO. He's now the co-founder and managing partner at States2 Capital. He's a long time Harvard Business School professor of sales and entrepreneurship and go-to-market. And he's the best-selling author of the Sales Acceleration Formula. Mark's new book,the science of scaling distills 25 years of research into a stage specific data driven roadmap for moving from product market fit to go to market fit and ultimately to growth and mode. Personal note, Mark and I have known each other for a few years here and he is a great person to know as a friend and certainly as a business colleague with all the incredible success he's had throughout his career.So let's jump into the four topics we will cover today. also just to remind us all to make sure we cover a little bit of the amazing things that Mark does for McLean Hospital and for mental health and in general throughout our country and the world. Four topics, why scale scientifically? The failure patterns leaders repeat and how to replace borrowed playbooks.with a measurable readiness model. We're go deeper into product market fit, defining ICP, instrumenting a leading indicator of retention that proves value creation and learning how to run fast learning loops within your organization. And then what does it mean to go to market fit and deeper there, how process hiring, demand gen, pricing and compensation.evolve to make revenue consistent and profitable. And then the dream, the growth and most, when you're pacing head count, choosing scalable channels, raising price with confidence and appropriateness, and running a metrics cadence board, an approach that drives trust throughout the entire organization. Mark, thanks so much for joining us. Welcome to Selling the Cloud.Mark Roberge (02:14)Hey, thank you, Mark. Thanks, KK. Appreciate all the preparation in that wonderful intro.Mark (02:20)Beautiful, thank you, Mark. So yeah, topic one, why scale scientifically? We see teams copy a hot playbook, know, ramp up spend, and then they learn six months later in many cases that renewals are soft. So they kind of work on the first side of the equation, but they really don't do the right planning and approach in making sure that they're really able to build long-term client relationships. The science says,manage to readiness and retention, not just the top line. We all know that companies are feeling that for the first time in a number of years as we move from the pandemic to a little more of a specific focus on making sure the growth is there and also that we get to profitability with many of these early stage SaaS companies. So what changes when a founder manages to the readiness and retention?instead of just revenue only. And what is one decision you would stop immediately when the data is noisy and contains more clutter than signals?Mark Roberge (03:25)Yeah, there's a lot to unpack there. So really a lot of the origination of that question comes back to my time after HubSpot before starting stage two. I had this interesting five year period where a lot of this work was originated. ⁓ I honestly did not intend to write another book, but sometimes you do a speech or write an article that⁓ becomes something bigger, I suppose, and people want more. And then you can start to see the timeliness and also the abstraction by which some of the framing could be applied. And so at the time I was teaching full-time at HBS, but also had a lot of time to participate in the startup ecosystem. As a board member, angel investor, advisor, I basically chose one company every quarter.to spend a day a week with and help them build out their opening sales org. ⁓ At the same time, I was a senior advisor at BCG and I was working with these massive global conglomerates on launching new products to drive revenue, top line growth and EBITDA. And I just found in both situations that there was an unnecessarily high failure rate because this concept of like,when you were ready to scale, like you got your product, you got your beta, you got your whatever. And like the time that you were ready to scale and the pacing was not analyzed strategically well enough. And that's what made me kind of start to reflect on these things on like ⁓ how can you use your own data to figure that out? In the startup arena,Pretty much it was aligned with like when they raised capital. They just happened to convince ⁓ VC to give them some capital and then that was the time that they were ready to scale supposedly because they had capital. And the pacing was essentially like copy whatever some other unicorn that just went public. What did they do 10 years ago the year after they raised their seed round?Mark (05:47)ThanksMark Roberge (05:47)Which like is, it doesn't make any sense. The contextual differences are so, so off. And then on the, on the big company size, it was like, Hey, we're going to launch this new product and engineering, you build it. We're going to launch it at our customer event in nine months and marketing, change the website and get the collateral going and sales, train all the salespeople and customer support, get all your scripts ready. And then they launched and wasted tons of sales motions on a product that didn't haveproduct market fit. So it's like two different diagnoses with the same issue. And that's what led to the research and understanding why some of these went, some of the companies that I'd worked with did an IPO, a billion dollar outcome, some went bankrupt. And what was the difference in their plan? And it was this three sequence framework of product market fit, then go to market fit and growth and moat is whatOver last decade, we've been coaching people to at State Shoe Capital and my work at Harvard Business School with my founders to have a more scientific approach to that. Now, to your point, Mark, you're asking about a focus on customer value creation. And I said the first step is product market fit, which isn't like profound. Normally when you go into like a classroom and ask like a bunch of 30 year old founders, how do know when you're ready to scale?they'll say product market fit, which is a great answer and a term that didn't exist in the year 2000. I think it was popularized by Eric Reese at Lean Startup or Steve Blank. it's like, the term caused us to progress as entrepreneurs. It's fantastic. But what's weird right now is when you turn around and ask those hundred entrepreneurs, what is product market fit, you get a hundred different answers. And half of them are like correlated to revenue and customer count.we have product market fit when we hit a million in revenue. We have product market fit when we have a ton of inbound leads. We have product market fit when we have 15 customers. Mark KK, we all know that like great sellers can sell ice to Eskimos. They can. ⁓ But Eskimos don't need ice. You know, when you can sell, you have market message fit. It just means you're going out there, people get interested and they buy.Mark (08:02)Yeah. Yeah.Mark Roberge (08:12)But the essence of product market fit means that whatever you promised them came true. It means they realized the value. It means they succeed with your product. And in a lot of the businesses that we work in, ⁓ that's best quantified by customer retention. Right? So that's really the backstory mark on your question of like, you know, why do we have to root the opening stages here in customer value creation and retention as opposed to top line revenue growth?And it's just because like acquiring a customer, generating revenue is just a step in the end process ultimately to get to the value realization.Mark (08:51)Mark, you've given us so many things to unpack here and we're gonna dive into all of those. Before I do though, I wanna make sure I cover one item you mentioned there that really, so many things hit me, but this one hit me directly. This concept of like taking the last similar company that went public or had a great exit and trying to replicate the plan there. That would be like Harvard Neuroscience researchers.saying we're going to start a new study, but we're only going to use information of 10 years old or longer. We're not going to look at anything in the last 10 years or five years. We're going to start from there. And we all know where that would bring us, and really not bring us in.Mark Roberge (09:33)And even worse thanthat, Mark, it's not just like someone doing a neuro study today and copy what was done in 2015, but also that they were in the potiatry department in 2015. That's really the fair analogy is like the context is so different. It's like, oh, we are bringing, you know, a cyber security AI agent to finance departments today.Mark (09:46)Yeah, that's a better one.KK Anderson (09:47)youMark (10:02)Right.Yeah.Mark Roberge (10:03)So let's copy what HubSpot did in 2010 as they brought marketing software to landscapers.Mark (10:11)Perfect, that is perfect. That is much better, love it. All right, KK, let's take us on. We're going upward.Mark Roberge (10:12)Ha ha ha ha ha.KK Anderson (10:19)First of all, Mark, thank you so much for giving us a pre-read of your book. I can already tell that it's going to 100 % become a Bible in our industry. I was just reading the other day that I think just this year alone, there were something like 2000 AI businesses that started up. So it's very timely. A lot of founders.Mark Roberge (10:22)You bet, KK.KK Anderson (10:39)starting up and they're going to be going, as I was reading this, was thinking of our clients and thinking, I wonder if Mark will let me forward this onto our clients because it's just, it's on the mark every step of the way. ⁓ retention, you talk about retention, I couldn't agree more. But that's lagging, you that's a lagging indicator. And so we need an early signal thatMark Roberge (11:01)Yes.KK Anderson (11:05)that actually helps us kind of figure that out. And so you talk about in the you know, that the framework and figuring out that that leading indicator of retention. So what is likeTalk to me about how you figure that out. It's a chicken or an egg. You need revenue, but you need retention. How do you, in those early stages, how do you do that?Mark Roberge (11:19)Mm-hmm.Yeah, that'sa great tee up on where we left off here, KK. So, you know, what we've got so far is like, okay, that makes sense. I have my product and I need to figure out my first North Star. And we're arguing so far that like, don't get in front of your company and say, we got the product. Let's get to a million in revenue. We're saying we got the product. Let's get to dozens of customers using this and being successful. Let's have our percent conversion fromsign customer to successful customer would be really high. And we're measuring that with retention. To your point, KK, like we can't, like a lot of times we don't really have a sense of the retention on the customers we signed up this month for like a year. You know, like, or at least like many, many months. And that's just too much time in startup world. So we need to pull that measurement back to right now.And that's where we come up with the term leading indicator of retention. this is a term that's been talked about for 20 years. I think we probably framed it at State Shoe Capital in this way. I think in sort of the B2C to B PLG ecosystems, they talk about it. was like the aha moment, even in like some consumer environments. ⁓ and what this is essentially, what can we observe of our customers experience with our product in the first month? That if we observe it.In the long term, they'll be with us forever. And if we don't, they're a significant risk of churn. That's essentially the leading indicator of retention. And I go so far to, I haven't found that there's a universal right answer, like wow, Dow ratio, weekly active user to daily active user ratio, or like time and product, like lead, you know, there's all these different ways of measuring. We can speak about how to come up with it for you. And this is one of those cool, like creative.elements of entrepreneurship is like you get to find this unique thing about your business that's magical. But let's talk about a framework around it. We talk about as P percent of customers do event every T time. So P percent of customers do event every T time. So now we just have to work on three variables. All right. So Slack has a famously documented example. Eighty percent of their customers send 2000 team messages every month.Wonderful. Right, like just imagine like the early days of Slack, there's like 10 people in the room, mostly engineers and designers, and the CEO says, we did it, we're launching. The first goal is to get to a million in revenue. You can imagine like what actions occur. Higher salespeople generate tons of leads, but versus the first goal is to get 80 % of our customers to send 2000 team messages every month.It's just such a healthier foundation of the business. And hopefully through that narrative, we understand that like how we can pull this back to measure this on a week by week, month by month basis. So we can go at startup pace. Now to your point, KK, there's this tension between maximizing revenue and maximizing customer success. This is not necessarily the same.We certainly like, I bet if the CEO of Slack stood up and said, let's get to a million in revenue versus let's get 80 % of our customers to send 2000 T messages every month, they probably would have gotten a million dollars in revenue faster, but it's highly likely that that customer base and revenue base would not have been as healthy. And that in the former situation, they probably would have ended up with a churn rate somewhere between20 and 40 percent. But by rooting it in the leading indicator of attention, they end up with a churn rate of five to 10 percent. So if I had to choose between getting to a million in revenue in two quarters, but ending up with a 30 percent churn rate versus getting to a million in revenue in three quarters with five percent churn rate, that's a no brainer.the latter's better. And so it just helps us like find that trade off is like revenue growth is critical in the success measure of a business, but it has to be healthy. And we have to have the right guard rails in there to check it.Mark (16:00)Yeah, very, ⁓ very cool. So, okay, so when a CEO says we're missing our number and the first thing they do, CEOs, even boards, we need more leads, we need more pipeline. And you've said in the past that that's rarely the right fix. And it's often this issue is that the system isn't ready to convert the leads it already has. How do you quickly test if that's true?Mark Roberge (16:14)Haha. Yeah.Mark (16:30)And if you can give us a few examples, stories of some fast checks that you use or any founder can use that they can run this week to decide if the problem is readiness versus volume.Mark Roberge (16:37)Yeah.Yeah, okay. So that progresses our discussion to the next phase of go to market fit. Okay, so what we have is like, we have a clear understanding, duh, the first thing we need to do is to get product market fit. But we have a much clearer definition of what product market fit is. I think if you go into Wikipedia and Google, know, or JackGBT, you know, product market fit, you get like a lot of like, it's just a feeling you know.So hopefully now we've like really quantified it and we know what we need to achieve. However, when we're sitting here and it's like the third month in a row and we've closed 10 customers and nine out of 10 customers have hit their leading indicator of attention, we are calling success on product money fit. Are we ready to scale? No, because of what Mark just asked. All we've proven is that we're gonna sign up 10 customers and 90 % of them are gonna be super successful in our product.We're not ready to add 10 salespeople because we still have a lot of questions. Like what's the process? How do we feed them? ⁓ What's the quota? What's the price of the product? I actually don't care that much about these things during the product market fit phase. I just care that these people are taking it seriously and they see success. But like now we have to figure out all these things out, like what Mark is saying around like, is it the lead flow of the process? So we call that go to market fit.Right? like product market fit is I'm, I'm confident that when I sign up a customer, they're going to be successful. Go to market fit as I can do that profitably. Now, when we talk about profitability here, we're not talking like gap accounting profitability out of your income statement, because that accounts for like your entire business, your, your, your office, your, your C-suite. These are some of these things don't necessarily scale with revenue. We want to isolate profitability here.to what scales with revenue and we often in our world talk about that as unit economics. So we need good unit economics. There's a lot of ways to measure unit economics. People that are listening here, you might say LTV to CAC. Lifetime value divided by customer acquisition cost greater than three. That's been a popular one for the last 20 years in SaaS. You might say payback period. How much does it cost to acquire a customer divided by how much do they pay us every month? There's burn ratio.There's a bunch of different like you and economics. And so like, let's just talk about LTV to CAC greater than three. Technically when a salesperson joins your company, picture a 27 year old account executive joins your company. And like, what's my job? The perfect answer is to generate an LTV to CAC greater than three. That would cause a 27 year old account executives had to explode.Like what, is that? How do I do that? So that's where we have to do the work. And we've kind of implicitly done this is we have to algebraically extract that target back to more understandable KPIs. Like how much is the contract? What's the close rate on leads? ⁓ how many, how many leads, how many meetings per month do I need to generate? Right. So that's, that's, you know, we can do that algebraically, you know, to extract it back to like, okay.Cost per lead, number of leads, close rate on leads, et cetera, et And so that's what our go-to-market formula becomes. And now all these things become important of like, how much are we charging for this thing? ⁓ What is our sales process? Do we have a scalable demand gen channel? I don't need one during the product market phase. I do need one now. And that's really what Mark's asking about is trying to get that like math and formula down.KK Anderson (20:29)really what we're asking about terms of.Mark Roberge (20:34)⁓ So now we're like through that process, we've got three or four salespeople. We have a quota. You know, we're generating, each of them is like either each salesperson is either generating or marketing is helping or SDRs are helping, but they're ending up with like 10 new meetings a month to start off. But the close rate isn't high enough to get to their number. How do we know if it deletes or the sales? That's what Mark's asking. That's really tricky.⁓ when you're at greater scale, it's a much easier answer. And this is an area that very few boards look at, which is individual rep performance and conversion rate. Cause if I have a team of 10 and four salespeople are constantly achieving a conversion rate of 30 % on their qualified meetings and other salespeople are converting 10%, then I know this is a sales process issue.Now, put aside like to changes in territory and all that kind of stuff, you got to make it fair for everybody. But like that helps me understand that it's, it's some sort of lead, you know, it's a sales process issue versus if I have 10 salespeople and they all have relatively the same conversion, despite probable variances in their skill sets, then, ⁓ you know, we probably have a lead volume or quality issue. And that's where I'd look, but the bottom line is like,You kind of attack both. know, our friend, Jaco at Winning by Design, like famously talks about like, you can do a 10 % improvement in every stage of the funnel. Like it's like, it's not like we're either going to double lead flow or double lead conversion. We, let's attack both and we're probably not going to be able to double both, but we probably can increase one by 10 % and one by the 20 % and the cumulative impact is massive.Mark (22:31)Incredible, incredible.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.