The Transaction

Carilu Dietrich & Maya Spivak joined Craig, Matt, and our amazing audience of GTM leaders at our GTM Tailwinds event this spring for a live recording where they shared insights on building founder and executive organic social media as a primary demand channel, why startups need to develop speed as a marketing skill, and why going viral on social doesn’t amount to what it seem for B2B companies.Carilu is the author of the Hypergrowth Leadership SubStack and is an all-star advisor and startup marketing leader.Maya is the Founder & Chief Marketer of Marketing.fan, a brand and creative marketing agency, and former VP of Marketing at Gretel.ai and Mux. Critical TakeawaysInvest in taste, or find someone who has it, before spending on out-of-home ad campaigns. Out-of-home advertising in major markets is constrained supply with non-trivial costs, and a mediocre creative execution wastes every dollar and actively damages brand perception at scale. Before committing budget to OOH, have someone with genuine creative discernment review the work, and if that person doesn't exist in-house, find them in your network before the media buy clears.Consistency beats virality for pipeline generation. Marketing teams should resist chasing one-off viral brand moments and instead build sustainable content cadences. Allocate budget and headcount to rhythm, not lottery tickets.Real differentiation for brands is about timing and originality, not just quality. The frameworks your competitors are copying right now are already losing their edge, and the window to do something genuinely surprising is always narrower than it seems.The pace of AI innovation and product development means that GTM leaders need to operationalize speed as a marketing capability. GTM teams need pre-built rapid-response playbooks for product launches, because the window to capitalize on a launch is now measured in hours, not weeks. For example, Carilu's product marketing team had 32 hours notice from OpenAI before a major LLM launch and shipped a full campaign within that window. Teams that don't have templates, approval chains, and asset libraries ready in advance will consistently miss the moment when momentum is highest.Edutainment is the new table stakes for B2B events, content, and advertising. Marketing teams should interrogate every content format and event experience against the question: is this entertaining enough to earn attention before it earns trust?Chapters00:00 Episode Preview00:50 Introducing Carilu Dietrich & Maya Spivak03:04 Are Viral Moments Worth Chasing for B2B Brands12:02 Real Market Momentum Starts with Product13:48 Edutainment Marketing Wins14:12 Building Out Bold Billboards Campaigns for B2B Brands16:29 Copycats and What Not to Do17:52 Examples of Marketing Creativity Beyond Billboards20:12 Startup Founder Social Media Playbook for B2B23:19 LinkedIn Organic Content Marketing Drives Enterprise Revenue27:29 Amplifying Customer Stories That Work31:26 Zig When Others Zag33:50 When B2B Brands Should Involve Influencers & The Need for Fast Launches37:49 Out Of Home Advertising Taste is CriticalJoin our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“The real problem that earlier stage companies have is they don't need advice. They need be able to do the work.” - Carilu Dietrich“If you're gonna spend the money, do it right. Make sure you have some taste.” - Maya SpivakConnect with CariluLinkedIn: https://www.linkedin.com/in/cariludietrich/ Carilu’s SubStack: https://www.carilu.com/ Carilu’s Past Episode: https://open.substack.com/pub/thetransaction/p/advisor-avengers-assembling-your Connect with MayaLinkedIn: https://www.linkedin.com/in/mayagrinbergspivak/ Marketing.fan Website: https://www.marketing.fan/ ShoutoutsGTMshift: https://gtmshift.com/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

The vast majority of companies that think they are running ABM (Account-Based Marketing) are not actually running ABM. Not only that, they wouldn’t recognize a real ABM strategy if one came up and slapped them in the face with a stack of direct mailers.Davis Potter is the CEO & Co-Founder of ForgeX, a research and advisory firm that helps B2B companies modernize their Account-Based Go To Market and AI strategies. Davis joins co-hosts Matt Amundson and Craig Rosenberg for an exploration of the current state of ABM (Account-Based Marketing), what it takes to drive impact of using AI in GTM Execution, and how to right-size the B2B marketing tactics to each account. Also, Craig uses a ‘Matt-ism’, Matt distinguishes cuddling from canoodling, and Producer Sam fixes a problem with his face. Critical TakeawaysThere are three core account-based marketing models: Enterprise ABM (1:1 and 1:few), Growth ABM (1:many at scale), and Deal Acceleration (targeted support for individual opps).Shift from short, one-off marketing campaigns to holistic, always-on programs that run continuously throughout the year. Build a playbook of ABM tactics (e.g., webinars, executive dinners, personalized landing pages, LinkedIn ads) and deploy them based on account tier and industry segment. This enables ongoing engagement and better adapts to complex B2B buying cycles.Select and tier accounts based on informed revenue potential, not just logo desirability or gut feel. Analyze first, second, and third-party signals, as well as customer LTV and microsegments, to prioritize accounts for deeper personalization and resource allocation. For example, reserve direct mail and executive engagement for tier one, while using scalable digital tactics for lower tiers.Unify your target account lists across sales, marketing, and customer success to drive alignment and efficiency. Instead of each function working from separate lists, create a single Go-To-Market account portfolio informed by revenue potential and engagement signals. AI can dramatically accelerate research, content personalization, and account list building, but only if you have a clear strategy first. Many companies are underutilizing AI or using it without a defined goal, leading to mediocre results.Chapters00:00 - Introducing Davis Potter, Founder of ForgeX08:00 - Quick Coldplay Concert Conundrum Recap10:00 - Davis’ first ABM Webinar horror story16:00 - Redefining Account-Based Marketing: Beyond the traditional pyramid18:00 - A new ABM segmentation model24:00 - The case for a unified Go-To-Market account portfolio27:00 - Growth ABM tactics that actually scale31:00 - Where AI fits into an ABM strategy (and where it doesn’t)39:00 - How shadow AI is reshaping GTM45:00 - Reporting, the board deck problem, and the MQL hangover49:00 - What your Revenue Team needs to measure in modern ABM53:00 - Replacing the Market Qualified Lead industrial complexJoin our Newsletter to never miss an episode & get bonus content: https://thetransaction.substack.com/Epic Quotes“One practitioner can't cover 50 accounts and actually leverage one-to-one.” - Davis PotterConnect with DavisLinkedIn: https://www.linkedin.com/in/davispotter62/ ForgeX Website: https://www.forgex.ai/ Revenue Xchange: https://open.spotify.com/show/7v2449do8UGuLAbilezi29?si=1a56c9a9a18d4550 ShoutoutsDemandbaseSangram Vajre: https://www.linkedin.com/in/sangramvajre/Sam McKenna: https://www.linkedin.com/in/samsalesli/ Sam McKenna’s Episode: https://open.substack.com/pub/thetransaction/p/social-selling-secrets-to-supercharge Dan Gottlieb: https://www.linkedin.com/in/danielpgottlieb/ Dan Gottlieb’s Episode: https://open.substack.com/pub/thetransaction/p/triple-t-pov-with-dan-gottlieb?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false Kerry Cunningham: https://www.linkedin.com/in/kerrycunningham/ Jon Miller: https://www.linkedin.com/in/jonmiller2/ Jon Miller’s Episode: https://open.substack.com/pub/thetransaction/p/building-trust-and-reputation-in

Even with all the newest, shiniest AI tools out there, successful, sustainable B2B sales growth is still built on nailing the basic sales skills.To provide a refresher on those basic B2B sales skills and more, we’re thrilled to introduce Tom Murtaugh, the Portfolio Operations Director at Nordic Capital, a leading sector-specialist private equity firm. Tom joins co-hosts Craig Rosenberg and Matt Amundson to discuss the importance of maintaining deal control, why revenue leaders need to understand the key activities that drive outcomes, and how to get your sales managers up to speed as they become more valuable with the implementation of AI.Plus, Tom helps Craig and Matt perform an autopsy on the failure of the sales enablement movement.Also, Craig once again references TOPO and Matt gets envious of a warm male embrace while also imparting the joys of parenthood.Critical TakeawaysWhat are the handful of activities that have a real impact on moving a deal forward for your company? While most organizations cannot empirically state which activities drive revenue, using modern data tools and call analysis, sales leaders can and should run correlation analyses to pinpoint and scale what top performers do.Sales leaders should be directly involved in late-stage enterprise deals, ensuring there is a clear, actionable joint execution plan for each opportunity. Top-down focus and hands-on deal reviews with sales leaders is critical to exceeding targets, even when the forecast looks grim. This level of engagement cannot be delegated or replaced by process alone.AI can accelerate analysis and experimentation, but it cannot define your core GTM motions or fix broken processes. If you haven’t figured out what works, AI will only amplify confusion. Go-To-Market leaders must first establish and validate the key behaviors and activities that move the needle before layering on automation or analytics. Sustainable revenue growth comes from robust GTM infrastructure, such as processes, platforms, and RevOps, that persist beyond any single CRO or sales leader.Sales enablement programs often fail when led by people without quota-carrying experience, devolving into classroom-style training that sellers reject. Shift to “sales excellence” roles, where former sales leaders who coach reps in the field, ride along on calls, and provide practical, trusted guidance. The most powerful enablement tools are those that let reps learn directly from top performers, such as reviewing Gong calls or shadowing high achievers. Tom shared that new reps who proactively sought out and emulated top sellers ramped faster and performed better. Make it easy for your team to access and learn from real sales conversations, not just static content.Chapters00:00 - Episode Preview03:51 - Introducing Tom Murtaugh, Portfolio Operations Director at Nordic Capital10:09 - How Improving Deal Control Turned Around a Terrible Quarter for Collibra21:02 - Understanding the Key Activities that Really Drive Outcomes in B2B Sales28:21 - Why Training First Line Sales Managers Needs to be a Priority for B2B GTM Leaders42:29 - Why the Sales Enablement Movement Ultimately Failed in Improving B2B Sales Orgs51:21 - The Role of RevOps in Building a Sustainable Infrastructure for the Revenue OrganizationSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“Any type of conversational analytics tool is the most powerful enablement tool that's out there right now, and people just need to use it.” - Tom Murtaugh“ Your sales manager is be going to become incredibly, even more important than they are today, because they're going to be the ones that even with a little bit of change, are going to have a lot of leverage over a lot of people.” - Tom MurtaughConnect with TomLinkedIn: https://www.linkedin.com/in/tom-murtaugh-1729b09/ Nordic Capital Website: https://www.nordiccapital.com/ ShoutoutsAmanda Murtaugh: https://www.linkedin.com/in/amandabuck143/ Ralph Barsi: https://www.linkedin.com/in/ralphbarsi/ Philip CardiNeil Harrington: https://www.linkedin.com/in/neildharrington/ Scott Albro: https://www.linkedin.com/in/scottalbro/ Jeff Goree: https://www.linkedin.com/in/jeffgoree/ Andy Byrne: https://www.linkedin.com/in/byrneandy/ Michael Hargis: https://www.linkedin.com/in/mhargis/ Pablo Dominguez: https://www.linkedin.com/in/pabtexas/ Echo Valley on Apple TV+ Starring Sydney Sweeney & Julianne Moore (Only rated a 6.3/10 on IMDb)Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

The old go-to-market playbook is broken, but in this episode we have a B2B SaaS founder who has actually figured out the new GTM playbook to grow in the current market.This SaaS savant is none other than the one and only David Boskovic, the CEO and Founder of Flatfile, which is the AI-powered data migration solution trusted by enterprise customers like ClickUp, HubSpot, Amazon, ADP, and Toast. David joins co-hosts Matt Amundson and Craig Rosenberg to outline how he and the GTM team at Flatfile developed their new AI-first go-to-market strategy, which is handling ten times the capacity of their previous GTM motions.David shares which of the 3 ways AI is being deployed works best, why you need to hire for individual contributors based on a candidate’s tastes, and why every Rev Ops team needs to hire an AI Engineer in order to stay ahead of the curve.Plus, David regales Matt and Craig with potentially the greatest story that’s ever been told on The Transaction, perhaps even better than ‘Maggots on a Plane.’Also, Craig threatens someone with having to wear a raccoon costume, Matt reveals the secret of what makes Craig great, and Sam the Producer experiments with some AI artwork.Critical TakeawaysWhen segmenting your ICP, segment into micro-verticals of 100–500 accounts, so you can then build tailored value propositions, demos, and collateral for each. AI allows this “luxury” level of personalization, which was once reserved for top accounts, to be applied to all targets. This dramatically improves first-call resonance, increases conversion rates, and differentiates your solution in competitive enterprise sales cycles.AI now allows you to turn things like costly enterprise-grade research into a commodity. Using tools like ChatGPT’s Deep Research or Perplexity you can produce insightful 40+ page market and account reports in hours instead of weeks. Validate quality by testing it with actual prospects. This “luxury” level of diligence, previously reserved for only top-tier accounts, can now be applied to every target at low cost.Having a CRM isn’t good enough. You should use AI to index every past customer/prospect interaction and extract key insights (budgets, pain points, workflows). Make this context instantly available to reps so every future conversation builds on a rich historical foundation.Every RevOps team, regardless of size, needs an AI Engineer to rapidly prototype and operationalize AI tools internally. If you want to remain ahead of the curve, you can’t be beholden to the slow development and innovation of tools from other SaaS companies.Operationalize everything in the company like a product. Treat your revenue org like a software system, debug bottlenecks, design orchestrations, and continuously iterate. The faster your GTM processes can be updated, the faster you can capitalize on new AI capabilities as they emerge.There are three main ways AI is deployed, Automation/Replacement, Augmentation, and Amplification. Amplification gives you the largest potential outcomes. To use the Amplification approach, deconstruct every GTM role into component tasks, give repetitive or low-value ones to AI, and keep humans focused on peaks of expertise like judgment, taste, and relationships.Chapters00:00 - Episode Preview01:32 - Introducing David Boskovic, The CEO & Founder of Flatfile02:49 - The Crazy, Raccoon-Filled Story Behind David Starting His First Company11:35 - Building an AI-First Go-To-Market Engine Internally from Scratch 15:07 - AI Lets You Do The ‘Unscalable’ At Scale with Quality and Affordability22:02 - Why Segmenting Prospects into Micro-Verticals Increases Your ABM Strategy’s Effectiveness33:26 - What it Takes to Spin Up an AI-First GTM Strategy & Why RevOps Teams Need an AI Engineer39:57 - Where is Software Going & Which of The 3 Ways to Implement AI Works Best47:12 - Why You Should Be Hiring Individual Contributors Based on Their Judgement51:34 - Sam Debuts Some Interesting AI Artwork of DavidSign up for our Newsletter: https://thetransaction.substack.com/Epic QuotesIt is incredibly hard to be optimistic enough about what’s possible” - David Boskovic“Dream your wildest dreams and see if you can make them happen. And if not, put them on the shelf, not for a year, but for a few weeks.” - David Boskovic“Part of what makes Craig great is his curiosity. He’s a lifetime learner.” - Matt AmundsonConnect with DavidLinkedIn: https://www.linkedin.com/in/dboskovic/ Website: https://flatfile.com/ ShoutoutsRory O'Driscoll: https://www.linkedin.com/in/roryodriscoll/ Scott Albro: https://www.linkedin.com/in/scottalbro/ Endgame: https://www.endgame.io/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Imagine you created a sales process so amazing that it was the only one customers actually enjoyed. Impossible? Today’s guest says no.Returning once again to grace this humble GTM-focused podcast with his immense intellect and immaculate presence is Brent Adamson, the co-author of The Challenger Sale and the upcoming new release, The Frame-Making Sale. Brent is back alongside Co-Hosts Matt Amundson and Craig Rosenberg to share how sellers can help B2B buyers become more confident in their own buying decisions, why “frame making” needs to be part of every seller's mindset, and how to tell powerful, emotionally engaging stories.Also, Craig confronts his own fleeting mortality, Matt says he likes “the big pullout”, and Sam the Producer contributes by swearing.Critical TakeawaysModern B2B buyers are overwhelmed and uncertain. Top-performing reps succeed by helping buyers build self-confidence in their decisions, not by pitching harder or throwing more whitepapers at them.The biggest predictor of successful SaaS deals isn’t objection handling, it’s whether the buyer believes they’re making a good decision. Sales teams should focus on guiding internal alignment and validating the decision process.Stop selling like you’re the expert and start selling like a guide. SaaS buyers want to see and hear what similar companies are doing when in their position. Social proof beats thought leadership when it comes to moving deals forward.Customer indecision is the real killer of your pipeline. B2B Buyers who feel overwhelmed delay action, your job is to make progress feel easy and safe.GTM leaders should train reps to speak with emotional clarity, using language that reflects how buyers feel, not just what they need to know.AI can’t replace human trust in B2B sales. Even as automation takes over task work, the real differentiator in SaaS GTM will be emotional connection and the ability to de-risk complex decisions.Vulnerability builds trust. Whether it’s storytelling, deal coaching, or just acknowledging awkward moments, honesty closes more than clever pitches.Sponsored SegmentInterested in becoming a sponsor of The Transaction? Contact transactionpod@samguertin.comChapters00:00 - Episode Preview02:05 - Introducing Brent Adamson & Reliving the Maggots on a Plane Story06:40 - Brent Recounts a Near-Death Experience, Courtesy of United Airlines12:26 - The Origins of Brent’s Latest B2B Sales Research16:15 - Why B2B Buyers Want a Rep-Free Buying Process & The Importance of Human Connection in Selling19:35 - Customer Decision Confidence is the Biggest Factor in Driving High-Quality, Low Regret Deals26:50 - B2B Sellers Need to Help SaaS Buyers Learn How to Buy Solutions Intelligently31:26 - Sales Psychology will Play an Even Larger Role in B2B Moving Forward37:49 - SaaS Sales Reps Need to Become Buying Coaches for their Prospects41:18 - How to Increase Customers’ Confidence in Their Own Buying Decisions48:32 - The Key to Telling Compelling, Emotionally Engaging Stories53:25 - How Addressing the Elephant in the Room, like Bloody Eyeballs, can Create Better Human Connections Sign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ When things like that make you nervous, uncomfortable, you don't run away from them you have to run right at 'em.” - Brent AdamsonConnect with Brent AdamsonLinkedIn: https://www.linkedin.com/in/brentadamson The Framemaking Sale: https://a.co/d/iQhqSzq Website: https://www.brentadamson.net/ A to B Insights Website: https://atobinsight.com/ ShoutoutsBrent’s Last Episode: https://open.substack.com/pub/thetransaction/p/reframing-b2b-sales-to-drive-buyerCoffee with Brent Adamson & Matt Heinz: https://www.heinzmarketing.com/events/podcast-coffee-with-brent-adamson-matt-heinz/

In the second episode of 'The Direct Deposit,' Matt Amundson and Craig Rosenberg dive into the astonishing growth of Cursor, a startup providing an AI code editor for software developers, that has secured three funding rounds and achieved $500 million ARR in less than a year—all without a traditional marketing strategy. Matt & Craig explore how Cursor's product-led growth go-to-market model and simple SaaS pricing tiers contribute to their success in both raising new funding rounds and recurring revenue. Plus, there's a debate over the relevance of a traditional Go-To-Market team for such early-stage startups creating AI products. We also briefly touch upon Matt's favorite movie, John Carpenter's 'Big Trouble in Little China.'Join the newsletter to get new episodes straight to your inbox! Join here: https://thetransaction.substack.com/Enjoy this episode? Share it with a friend!Believe it or not, even in the tech-fueled world we live in, the number one way podcasts grow is word of mouth. So, if you learned something, lost your cool at something, or laughed at something from the show, give us a hand by sharing this with someone else who will get that same value from the show, regardless if it's education, entertainment, or outrage-inducing.