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From 10 epsHost
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Recent episodes
How We're Building Granola Into the Most Beloved Product in AI w/ Bardia Shahali, VP Sales @ Granola
Jun 23, 2026
Unknown duration
How To Hire Sales Reps Like a Moneyball GM W/ Navid Zolfaghari, Chief Sales Officer @ Zapier
Jun 16, 2026
Unknown duration
How The Best Salespeople Are Building Agents in GTM w/ Roy Mathew, Head of Sales @ Gumloop
Jun 9, 2026
Unknown duration
Every Startup Is Lying to You, So Here's How to Pick the Right One w/ Glenn Rachlin
Jun 2, 2026
Unknown duration
How Harvey Scaled GTM to an 11B Valuation w/ Rob Saliterman, VP of Sales @ Harvey
May 26, 2026
Unknown duration
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 6/23/26 |  How We're Building Granola Into the Most Beloved Product in AI w/ Bardia Shahali, VP Sales @ Granola | Bardia Shahali is the VP of Sales at Granola, one of the most beloved products in tech right now, where he's turning a product people are obsessed with into a real enterprise GTM motion.He's spent his career betting early on the right companies. He learned to sell as an AE at BlackLine (which went public), moved to San Francisco for Intercom, then joined Teleport as its first sales hire at seed stage and helped take it from $0 to $20M ARR and a $1B valuation. In early 2024 he joined Fireworks at Series A and helped scale it, before landing at Granola. Along the way, he's advised a number of 0-to-1 companies building their first go-to-market engine.He met his wife at Intercom, sold his house and moved his family (plus two dogs) back to SF so he wouldn't miss the AI wave, and talks into Wispr Flow so much his wife says it's "what old people do." He's also a prolific writer on sales and GTM, and once got rejected from his dream MBA program and decided to go build startups instead.Timestamps(00:00) Intro(01:22) Welcome to the Crew Podcast + Sponsor(02:47) Granola: One of the Most Beloved Products in Tech(03:13) The Booth Rejection & Bardia's Career Arc(06:18) Moving Back to SF for the AI Wave(08:03) What Actually Makes Granola Special(10:31) Is the Entry-Level Sales Role Dead?(12:06) Killing the Busywork, Not the Job (Claude Co-Work)(18:29) Build Your GTM Org Around Your Sales Cycle(24:22) Why $100M ARR Doesn't Mean What It Used To(26:42) The Hiring Mistake That Wrecks AI Companies(32:38) The AI Tools Bardia Can't Live Without(35:34) The Steak Dinner Is Dead(40:13) How To Choose the Right Company in AI(45:23) Founder-Market Fit, Market Pull & TAM(48:10) Interviewing for Mindset Over Mechanics(49:39) The Outreach That Stood Out(52:10) The GTM Orgs Bardia Admires (Figma & Cursor)(54:11) The "Order Taker" Debate(57:27) Why 90% of AI Unicorns Are in SF(01:00:56) Granola's Roadmap & What's NextAbout The Crew PodcastThe Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies.Every week, host Chris Balestras, partner @ Crew (an advisory, recruiting, investing, & media firm for seed through series C AI-natives) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today.No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.About CrewCrew is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.Where to Find CrewLinkedIn: https://www.linkedin.com/company/crewgtmYouTube: https://www.youtube.com/@thecrewgtmNewsletter: https://www.withcrew.blog/Website: https://www.withcrew.ai/This episode is brought to you by Salesgraph.Enterprise deals don't usually slip because of effort - they slip because the technical gap didn't get caught in time. A champion goes quiet, an objection never got handled, procurement shows up late. That context lives in your calls, Slack threads, and top reps' heads, and it doesn't transfer when you hire.Salesgraph pulls from your Salesforce, Gong, Granola, docs, and Slack, then writes the things that move deals forward - gap analyses, champion business cases, and pre-call briefs. It's like a company-specific GTM brain. YC-backed, built by founders who lived this at Mintlify.Get a free GTM audit → salesgraph.com/gtm-audit | — | ||||||
| 6/16/26 | How To Hire Sales Reps Like a Moneyball GM W/ Navid Zolfaghari, Chief Sales Officer @ Zapier | Navid's BackgroundNavid Zolfaghari is the Chief Sales Officer at Zapier, where he's leading the push to move one of PLG's most iconic companies up-market into the enterprise.Before Zapier, Navid spent six years at Branch, joining at roughly $500K in revenue and helping scale it to ~$100M. He then went to Metronome to go deeper on usage-based pricing. Early in his career, he was at a retail analytics startup and before that he co-founded a company focused on micro-location data and beacons.Navid got his start at Wildfire, which he joined at ~20 people and watched grow to 400 people before it was acquired by Google. He spent a couple of years at Google post-acquisition, which was plenty long enough to learn that the big-company lifestyle wasn't for him. He's also a poker player, a Miami Heat loyalist, and shamelessly pours his milk before cereal (yes, we think it’s crazy too).Timestamps(00:00) Intro & Why Navid Made the Trip from Redwood City(11:16) Navid's Background: Two-Time Founder to GTM Leader at Wildfire, Branch, Metronome & Zapier(13:07) The Google Acquisition Story & Knowing Big Company Life Wasn't for Him(15:00) What Zapier Actually Is Now: Agents, MCP & the Evolution Beyond Hand-Rolled Zaps(15:35) AI Fluency at Zapier: The Four-Tier Rubric & Why "I Use ChatGPT" Is Now Unacceptable(21:34) The War Council: An AI Advisory Board the Entire Exec Team Uses(23:38) How Zapier Fits Into the MCP & Claude Co-Work Era(34:43) Most Common Personas & the Rise of the "Head of AI Transformation"(36:22) The Unified Value System: How One AE Replaced an Entire Sales Value Engineering Function(38:36) Tools You'd Have to Rip From His Cold Dead Hands(42:03) The Blueprint for Excellence: Startup Fit, Business Athleticism & Purposeful Drive(53:57) Love to Win vs. Hate to Lose: How He Evaluates Competitive Drive(01:05:28) The Consultant Mindset: What's Actually Changed in the Sales ArchetypeAbout The Crew PodcastThe Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies.Every week, host Chris Balestras, partner @ Crew (an advisory, recruiting, investing, & media firm for seed through series C AI-natives) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today.No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.About CrewCrew is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.Where to Find CrewLinkedIn: https://www.linkedin.com/company/vibescaling/https://www.linkedin.com/company/crewgtmYouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxghttps://www.youtube.com/@thecrewgtmNewsletter: https://www.vibescaling.blog/https://www.withcrew.blog/Website: https://www.withcrew.ai/This episode is brought to you by Salesgraph.Enterprise deals don't usually slip because of effort - they slip because the technical gap didn't get caught in time. A champion goes quiet, an objection never got handled, procurement shows up late. That context lives in your calls, Slack threads, and top reps' heads, and it doesn't transfer when you hire.Salesgraph pulls from your Salesforce, Gong, Granola, docs, and Slack, then writes the things that move deals forward - gap analyses, champion business cases, and pre-call briefs. It's like a company-specific GTM brain. YC-backed, built by founders who lived this at Mintlify.Get a free GTM audit → salesgraph.com/gtm-audit | — | ||||||
| 6/9/26 | How The Best Salespeople Are Building Agents in GTM w/ Roy Mathew, Head of Sales @ Gumloop | Roy’s BackgroundRoy Mathew is the Head of Sales at Gumloop, one of the leading AI agent builders helping companies automate workflows across sales, marketing, and IT. Before Gumloop, Roy spent several years at Airtable where he started as a growth lead, pitched the CEO to let him carry a bag, and helped build the sales playbook from scratch. After Airtable he followed his former head of sales to Recurrency, an ERP-adjacent platform selling into distributors and wholesalers. Before all of that, Roy was a special situations options trader, worked on the marketing team at Box, co-founded an automotive technology company called UQuote, and did a stint at Elastic. He's a Harvard undergrad, Wharton MBA, and has one of the more unconventional paths into sales leadership you'll hear.Timestamps:(00:00) Intro & The Sell-Grill-Sell Sandwich: Why Hiring Managers Kill Their Own Pipeline(02:39) Roy's First Call Horror Story: Getting Deal-Reviewed for a VP Role(04:55) From Options Trader to Box to Founding a Company: Roy's Roundabout Path Into Sales(09:47) Joining Airtable as Employee 25: How a Guy Looking Over His Shoulder Changed Everything(11:04) Pitching the CEO: "Let Me Carry the Bag or I'm Just the Spreadsheet Person"(14:46) How to Evaluate an Early-Stage Company: Beyond the Investor Logos(17:58) Why He Chose Gumloop: The Two-Week Interview That Threw His Framework Out the Window(20:17) MCP, Co-Work, and the Agent Era: A Non-Technical Explainer(26:06) The Blank Page Problem: How Gumloop Thinks About Personas vs. Use Cases vs. Industry(31:00) The Pre-Call Agent Stack: Email, Slack, Gong, Granola, and Web Scrapers in One Brief(35:34) The Post-Call Agent Stack: Recap Emails, CRM Updates, Linear Tickets, and Product Feedback(38:03) The Self-Improvement Loop: An Agent That Watches What You Actually Send(42:30) Agents for Sales Leaders: Process Adherence, Pipeline Inspection, and SPICED Monitoring(50:40) GTM Mafias: Why the Slack Mafia Might Be Overhyped(52:21) Blue-Chip-Only Resumes Are a Red Flag: "You Want Someone Dangerous at a Bad Company"(57:15) The Outbound Play That Actually Works: Gumball Machines and Speaking Like a Human(59:35) What Roy Looks For When Hiring at Gumloop Right NowAbout The Crew PodcastThe Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies.Every week, host Chris Balestras, partner @ Crew (an advisory, recruiting, investing, & media firm for seed through series C AI-natives) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today.No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.About CrewCrew is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.Where to Find CrewLinkedIn: https://www.linkedin.com/company/vibescaling/https://www.linkedin.com/company/crewgtmYouTube: https://www.youtube.com/@thecrewgtmNewsletter: https://www.withcrew.blog/Website: https://www.withcrew.ai/This episode is brought to you by Salesgraph.Enterprise deals don't usually slip because of effort - they slip because the technical gap didn't get caught in time. A champion goes quiet, an objection never got handled, procurement shows up late. That context lives in your calls, Slack threads, and top reps' heads, and it doesn't transfer when you hire.Salesgraph pulls from your Salesforce, Gong, Granola, docs, and Slack, then writes the things that move deals forward - gap analyses, champion business cases, and pre-call briefs. It's like a company-specific GTM brain. YC-backed, built by founders who lived this at Mintlify.Get a free GTM audit → salesgraph.com/gtm-audit | — | ||||||
| 6/2/26 |  Every Startup Is Lying to You, So Here's How to Pick the Right One w/ Glenn Rachlin | Glenn Rachlin is the VP of Worldwide Sales at Blockaid, a cybersecurity company protecting the blockchain and crypto ecosystem from malicious attacks.Before Blockaid, Glenn was an early sales hire at Alchemy, the infrastructure layer for crypto, where he helped grow the company from a $500M valuation to $10B and scaled the team from 10 to 130. Prior to his startup chapter, Glenn spent years at AWS during its era of dominance, where he experienced the wild "horse trading" culture of swapping accounts and reps between territories. He cut his teeth earlier at EMC (the classic 1980s sales org with Wolf of Wall Street energy) and IBM (old school, multi-generational, consulting DNA).Glenn is a Long Island native, a Bitcoin maxi who dollar-cost-averages into the ETF, a student of the Hunters and Unicorns podcast lineage, and a member of the Cyber Startups Network VC group.Timestamps(00:00) Intro(01:03) Glenn's Background: IBM → EMC → AWS → Alchemy → Blockaid(02:20) Why He Left AWS After Years at the World's Hottest Company(03:47) Cold-Calling CROs From Podcasts and Forcing Them to Be His Advisors(05:03) Getting Rejected by AWS Twice: The Loop Interview and What It Takes(06:53) Why Big-Company Reps Struggle at Startups (The Two-Sale Problem)(08:06) The "Order Taker" Debate: When Easy Mode Is Actually the Smart Move(09:58) Horse Trading at AWS: Swapping Accounts and Reps Like Sports Trades(12:07) Sales Orgs Glenn Admires Most: Scale AI, Wiz, Datadog, Snowflake(18:09) How to Choose the Right Startup: Founder Pedigree and Backchannel Everything(19:49) Every Startup Is a Complete Shit Show (And That's the Point)(25:28) Assessing Market Pull Before You Join(28:59) The Chainalysis Story: $100M to $8B Because of One Regulation(30:55) AI in Sales: Translating Hebrew in Slack and Vulnerability-Based Prospecting(32:35) Why Israeli Military Intelligence Breeds the Best Startup Founders(39:01) How AI Is Changing the Sales Profile and Quota Expectations(42:30) Why You Can't Hire Slow and Win(46:43) Glenn's Hot Take: If You Didn't Get the Job, You Didn't Try Hard Enough(50:15) What Doesn't Work in Sales Anymore: Remote Is Dying, Cold Calling Is Back(53:07) Bitcoin, Dollar-Cost Averaging, and Where Glenn Puts His Money(54:41) Creative Ways to Get in Front of Anyone (Without Being Weird)About The Crew PodcastThe Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies.Every week, host Chris Balestras, partner @ Crew (an advisory, recruiting, investing, & media firm for seed through series C AI-natives) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today.No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.About CrewCrew is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.Where to Find CrewLinkedIn: https://www.linkedin.com/company/vibescaling/https://www.linkedin.com/company/crewgtmYouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxghttps://www.youtube.com/@thecrewgtmNewsletter: https://www.vibescaling.blog/https://www.withcrew.blog/Website: https://www.withcrew.ai/This episode is brought to you by Salesgraph.Enterprise deals don't usually slip because of effort - they slip because the technical gap didn't get caught in time. A champion goes quiet, an objection never got handled, procurement shows up late. That context lives in your calls, Slack threads, and top reps' heads, and it doesn't transfer when you hire.Salesgraph pulls from your Salesforce, Gong, Granola, docs, and Slack, then writes the things that move deals forward - gap analyses, champion business cases, and pre-call briefs. It's like a company-specific GTM brain. YC-backed, built by founders who lived this at Mintlify.Get a free GTM audit → salesgraph.com/gtm-audit | — | ||||||
| 5/26/26 | How Harvey Scaled GTM to an 11B Valuation w/ Rob Saliterman, VP of Sales @ Harvey | Rob’s BackgroundRob Saliterman is the VP of Sales at Harvey, the AI platform for legal professionals that's grown from two customers to a $11B valuation in under two years.Before Harvey, Rob spent five years at Stripe leading teams focused on B2B vertical software platforms. Prior to that, he held sales and leadership roles at Snapchat and Google, where he got his start running political advertising sales after a career in government, including time in the White House.Rob got into sales through an unlikely door: Google needed someone who understood politics and could learn digital marketing. He'd never carried a bag before. He has an MBA from Harvard Business School and is one of the few people in AI sales leadership who came up through government and political communications rather than traditional SaaS.Discussed In This EpisodeWhy he cold messaged Harvey's co-founder on LinkedIn after reading an OpenAI portfolio list (and how he got a reply)Hiring a VP of Sales before hiring AEs: why Harvey did it backwards on purposeThe interview question that gives the most signal: "Walk me through a big deal: how you created it, converted the champion, and closed it" Selling to lawyers who've never bought software before and why testing for non-technical communication matters more than legal expertiseNo champion, no deal (except when it's worth it to slog through without one)Why pipe gen is a muscle memory sport and the first thing reps deprioritize when they shouldn'tPersonalizing demos using a lawyer's own public filings and why lawyers lean in when you give them something to argue withHiring management consultants alongside AEs to solve the change management objection The managing partner test: why consistency and credibility matter more than polishHow Harvey went from five PDFs you could ask questions about to a collaboration platform with 1,000+ customersTimestamps(00:00) Intro(07:45) Rob's Background: White House → Google → Snapchat → Stripe → Harvey(08:40) Why He Cold Messaged Harvey's Co-Founder on LinkedIn(10:24) The Moment He Knew Harvey Was Real: A Lawyer's Outside Counsel Test(12:37) Career Path: How a Government Background Translates to Sales(15:16) The Common Thread Across Google, Stripe, and Harvey: Selling Something New(17:14) Hiring a VP of Sales Before AEs: Why Harvey Did It Backwards(21:05) What Makes a Great Harvey AE: Selling to Non-Technical Buyers(27:18) How the Hiring Profile Changed From 10 Reps to 100(29:59) Pipe Gen at Harvey: Why the Fundamentals Still Work(34:42) Why Pipe Gen Is the First Thing Reps Deprioritize(36:44) Personalizing Demos With a Lawyer's Own Public Filings(40:05) Rev Ops as an Early Hire: Why Harvey Built Infrastructure From Day One(44:34) No Champion, No Deal (Except When It's Worth Breaking That Rule)(49:49) Change Management as a Sales Differentiator(52:00) The Managing Partner Test: Consistency Over Polish(55:19) Where Harvey's Best AEs Actually Come From(58:32) The "Why Now" Interview Question That Separates Good From Great(01:00:00) Wrap + Where Harvey Is HeadedAbout The Crew PodcastThe Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies.Every week, host Chris Balestras, partner @ Crew (an advisory, recruiting, investing, & media firm for seed through series C AI-natives) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today.No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.About CrewCrew is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.Where to Find CrewLinkedIn: https://www.linkedin.com/company/vibescaling/YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_KhrlxgNewsletter: https://www.withcrew.blog/Website: https://www.withcrew.ai/ | — | ||||||
| 5/19/26 | Why The Best Sales Rep You Interview Is Probably Your Worst Hire with Mike Heller, Partner @ Floodgate | Mike’s BackgroundMike Heller is a Partner at Floodgate, one of the most respected seed-stage venture firms in Silicon Valley known for early bets on companies like Twitch, Lyft, and Twitter.Before Floodgate, Mike spent four and a half years at Clearbit where he joined as the first sales and marketing hire and helped grow the business from just over $1M to nearly $15M ARR. Prior to that, he was an early enterprise seller at Dropbox during the era when it was a "nearly impossible" sell, competing against free bundled solutions from Google and Microsoft while Box was building everything the enterprise buyer wanted.Mike got his start in Singapore running sales for a test prep business, then got pulled into Dropbox's experimental bottoms-up sales motion before it even had a name. After Clearbit he built a GTM advisory practice working with pre-PMF founders, which eventually led him to the investor seat at Floodgate.Discussed In This Episode Why the Dropbox enterprise sale was so hard and why that difficulty bred an elite generation of sellers The "smooth talker" trap: why the most impressive interview candidate is often your worst hire Why founders hire salespeople too early and what they're actually trying to solve The Jason Lemkin "hire two AEs" rule and when it's completely wrong How Mike grew Clearbit from ~$1M to ~$15M as the first GTM hire Why he stopped wanting to be a sales leader, and what he chased instead How giving free feedback on founder sales calls built his advisory business, deal flow, and investor career The two traits Floodgate looks for before writing a check: speed and "super learning" Why the Wayback Machine is an underrated founder diligence tool Where AI is actually showing up in sales and where it's still not touching the core of the jobTimestamps(00:00) Intro(01:35) Mike's Background: Singapore → Dropbox → Clearbit → Floodgate(04:09) What Made the Dropbox Sales Culture So Elite(05:02) Why Selling Dropbox Enterprise Was "Nearly Impossible"(06:01) Leaving Dropbox: Choosing Clearbit Over Slack and Segment(09:58) Growing Clearbit From $1M to $15M as First GTM Hire(11:17) Why Mike Stopped Wanting to Be a Sales Leader(12:48) Building an Angel Investing and Advisory Career(14:37) Common Mistakes Founders Make on Discovery Calls(15:43) When Founders Should (and Shouldn't) Hire Their First AE(18:22) Why Hiring Too Early Creates Bad Revenue(20:22) From Advisory to Floodgate: Choosing the VC Path(25:39) Do Operators Make Better Investors?(27:56) The Two Traits That Matter Before Writing a Check: Speed + Super Learning(30:40) The Wayback Machine as a Founder Diligence Tool(32:15) AI in the Sales Tech Landscape: What's Real and What's Not(36:56) Career Advice: Stop Optimizing for Logos, Chase Energy(40:08) The "Smooth Talker" Trap in Sales Hiring(43:55) Should Founding AEs Get More Equity?(48:13) Why You Shouldn't Optimize Your Fundraise Around a GTM-Focused VC(50:19) The Future of Sales: Reps Who Can Ship CodeAbout The Vibescaling PodcastThe Vibescaling podcast interviews GTM leaders and investors at top AI startups and early-stage companies.Every week, host Chris Balestras, partner @ Vibescaling (an advisory, recruiting, investing, & media firm for seed through series C AI-natives) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today.No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.About VibescalingVibescaling is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.Where to Find VibescalingLinkedIn: https://www.linkedin.com/company/vibescaling/YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_KhrlxgNewsletter: https://www.vibescaling.blog/Website: https://www.vibescaling.ai/ | — | ||||||
| 5/12/26 | How We Built Profound’s GTM Motion To A $1B+ Valuation w/ Mark Ebert, SVP of Revenue @ Profound | Mark’s BackgroundMark Ebert is SVP of Revenue at Profound, the answer engine optimization platform helping brands win in the new world of AI search. Before Profound, Mark spent nearly nine years at 6sense, joining to build out the East Coast sales team. After an eventful day one, including one AE quitting and the remaining one begging him to stay, Mark went on to help build the company into the ABM category leader. Before 6sense, Mark sold and led enterprise teams at Responsys / Oracle Marketing Cloud during the marketing cloud wars against Salesforce and Adobe. He started his career as a BDR at Experian right out of college, after his dad’s sage advice that since he wasn't going to be a doctor or a banker, he should find a way to get into sales. Mark is based in Boston, a history buff with a soft spot for Revolutionary War battle planning, and probably the most relentlessly optimistic sales leader you'll meet.Discussed In This EpisodeWhy enablement teams shouldn't actually be running enablement and who should instead when product ships dailyThe two questions every new AE at an AI-native company should be obsessed with answering in week oneThe "leave them alone on the sales floor" test for spotting a sales leader who's actually a doer vs. a dashboard leaderWhy he'd rather hire the rep who crushed it at the #3 product company than the rep who hit 150% at the obvious category leaderWhat World War 2 battle planning teaches him about running a POCThe "see the movie before it plays" framework and how the best reps whiteboard the 3 most likely deal paths and pre-plan their counter-movesWhy the B2B sales funnel is collapsing inside of LLMs (and the data on what 80% of buyers do after they leave ChatGPT)Marketing to your new "ultra customer": the LLM itselfThe Jolt Effect: why most deals die from fear of screwing up, not fear of cost and how to surface that fear before the buyer doesAI tooling the team is leaning on right now (Dust, Granola) and how Mark uses an AI sales bot to grade his team's first calls overnightTimestamps:(00:00) Intro, What Profound Is Building & Why Mark Joined(02:14) From Experian BDR to Oracle Marketing Cloud: Why Mark Left for Sixth Sense(07:36) Why Your Enablement Team Shouldn't Run Enablement(13:38) The Two Questions Every New AE Should Obsess Over in Week One(17:05) The Sales Leader Who Won't Sell Is a Liability: The "Leave Them on the Sales Floor" Test(22:21) The 3-Path Whiteboard: How Great Reps See the Deal Before It Plays(23:24) Confidence vs. Overconfidence: The Hire Mark Worries About(27:09) What World War 2 Teaches Mark About Running B2B Evaluations(29:36) Why Hiring from the #3 Product Beats Hiring from the Category Leader(31:30) The Quota Attainment Question Most Hiring Leaders Read Wrong(33:30) The B2B Funnel Is Collapsing Inside ChatGPT(37:31) Marketing to Your New "Ultra Customer": The LLM Itself(38:38) Rapid Fire: Staying Upbeat, Dust, Granola & The Jolt EffectAbout The Vibescaling PodcastThe Vibescaling podcast interviews GTM leaders and investors at top AI startups and early-stage companies.Every week, host Chris Balestras, partner @ Vibescaling (an advisory, recruiting, investing, & media firm for seed through series C AI-natives) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today.No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.About VibescalingVibescaling is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.Where to Find VibescalingLinkedIn: https://www.linkedin.com/company/vibescaling/YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_KhrlxgNewsletter: https://www.vibescaling.blog/Website: https://www.vibescaling.ai/ | — | ||||||
| 5/5/26 | Why "AI for Finance" Is Meaningless & Why Bankers Make the Best Sellers W/ James White @ Rogo | James White is the VP of Sales at Rogo, one of the hottest AI companies in finance, building AI for investment banking and rapidly landing the biggest institutional logos on Wall Street. Before Rogo, James helped build and sell Sentieo (acquired by AlphaSense, now valued at ~$8B), where he sold financial search tools to hedge funds and asset managers. Prior to that, he was an early sales hire at PerfectData (acquired by Nutanix pre-IPO), where he learned enterprise sales from a team of ex-Data Domain reps and helped scale the company from 0 to $20M in ARR. James started his career working at CompUSA in high school, turned down Morgan Stanley to join Apple, and then caught the startup bug and hasn’t looked back since. He's a Houston native who went west to Berkeley with one goal: build companies.Discussed in this episode: Why "AI for finance" is like saying "software for business" (and why both are meaningless phrases) How Rogo sells into MDs at banks who can barely navigate their own tools but have incredible judgment The "Einstein starts at the bank tomorrow" analogy for explaining AI adoption to skeptics Why investment banking's compliance and infosec moat is actually Rogo's moat The GTM Associate program: how Rogo converts burned-out junior bankers into elite sellers Why renaming "SDR" to "GTM Associate" isn't just a branding unlock but a recruiting one too The comp structure pitch that gets bankers to take a pay cut (and why they do it) How Alex Pall from The Chainsmokers became Rogo's most productive SDR Why Rogo's top-performing AE is also the #1 user of Rogo (more than the CEO) Product obsession as the new screening filter in hiring The Renaissance Technologies thesis: take a banker, teach them sales, and watch them dominateTimestamps00:00 - Cold Open: Why Finance is Deterministic and AI Isn't01:24 - Intro & James's Origin Story: Stock Picking at CompUSA03:42 - Breaking Into Tech Sales at Pure Storage06:34 - Apple, Morgan Stanley & Choosing the Startup Path08:23 - Joining Sentieo & Selling to Hedge Funds11:15 - Why Selling AI is Different from Selling SaaS12:31 - Solving for Hallucinations in High-Stakes Finance15:18 - Why MDs Are Surprisingly Heavy AI Users17:24 - Structuring Rogo's Enterprise GTM Team20:57 - Why Bankers Make Great Salespeople (The Renaissance Thesis)22:41 - "AI for Finance" is Meaningless: Why Rogo Picked IB26:01 - Why Anthropic Won't Eat the App Layer31:14 - Defining the AI-Native Seller34:33 - Building a Sales Team from Burned-Out Junior Bankers39:07 - The Chainsmokers' Alex Pall: Rogo's Best SDR42:16 - Reimagining GTM Workflows with AI45:38 - What Rogo is Hiring ForAbout The Vibescaling PodcastThe Vibescaling podcast interviews GTM leaders and investors at top AI startups and early-stage companies.Every week, host Chris Balestras, partner @ Vibescaling (an advisory, recruiting, investing, & media firm for seed through series C AI-natives) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today.No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.About VibescalingVibescaling is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.Where to Find VibescalingLinkedIn: https://www.linkedin.com/company/vibescaling/YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_KhrlxgNewsletter: https://www.vibescaling.blog/Website: https://www.vibescaling.ai/ | — | ||||||
| 4/28/26 | The Old Sales Playbook Is Dead: Hiring + Selling In The AI Era w/ Jacquelyn Goldberg, VP Sales @ Unframe AI | Jacquelyn's BackgroundJacquelyn Goldberg is the VP of Sales at Unframe, which has been dubbed the "Palantir for AI.” Unframe works with Fortune 500 companies to identify business problems worth solving and ship production-ready solutions to them in days, not months.Before Unframe, Jacquelyn was the VP of Global Revenue at Sama AI. She spent most of her career in machine learning-adjacent startups as an early go-to-market hire, then pivoted fully into AI about five years ago, before most salespeople had even heard the term artificial intelligence. She's an early-stage lifer who's built GTM at companies before their sales playbook exists, and has been in the arena long enough to know which hires actually work and which ones just can interview well.Timestamps(00:00) Intro & What Unframe Does (Palantir for AI)(05:50) Why Every AI Startup Sounded the Same & How Jacquelyn Evaluated Defensibility(08:05) Industries Adopting AI Fastest (Real Estate, Financial Services, Healthcare)(09:20) How Unframe AI Lands & Expands Inside Enterprise Accounts(10:50) The 50% Assessment Failure Rate & What Candidates Keep Getting Wrong(13:40) Discovery as a Give-Get, Not an Interrogation(15:55) What Jacquelyn Actually Means by Intellectual Curiosity and Grit(18:25) Following the Cookie Trail: How to Show Curiosity in an Interview(20:25) Can You Teach Discovery? What's DNA vs. Trainable(23:05) AI Literacy Tiers: From Not Using It to Vibe Coding(25:15) How to Prove Grit When You've Never Worked at a Startup(26:45) "It Functioned Like a Startup" and Why That's Not the Same Thing as One(28:25) Most Pipeline Problems Are Actually Thinking Problems(31:10) What's Actually Working in Outbound Right Now(32:55) The Rolodex Is the Lowest Thing You Should Hire For(34:45) Industry Expertise: When It Matters and When It Doesn't(37:00) Radical Honesty: Telling Candidates Every Reason Not to Join(38:40) Two Weeks Feels Like Six Months at the AI Company Pace(40:00) Why Big Company Reps Struggle at Startups (It's Not Talent)(43:35) How Enterprise Selling Changed Post-COVID(47:50) Is Sales Dead? Why AI Makes Sellers Better, Not Obsolete(49:20) The Future of Entry-Level Sales & Why Universities Need to Catch Up(51:50) Alpha School and Rethinking How People Find Their CareerAbout The Vibescaling PodcastThe Vibescaling podcast interviews GTM leaders and investors at top AI startups and early-stage companies.Every week, host Chris Balestras, partner @ Vibescaling (an advisory, recruiting, investing, & media firm for seed through series C AI-natives) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today.No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.About VibescalingVibescaling is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.Where to Find VibescalingLinkedIn: https://www.linkedin.com/company/vibescaling/YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_KhrlxgNewsletter: https://www.vibescaling.blog/Website: https://www.vibescaling.ai/ | — | ||||||
| 4/21/26 | Tell Them the Movie Before They Watch It: Enterprise Sales, Champion Building & the No-Pilot Stance W/ Adam Ali, SVP Revenue @ Rox✨ | enterprise saleschampion building+3 | Adam Ali | RoxRubrik+12 | — | AI-native revenue operating systemno-pilot stance+2 | — | 57m 48s | |
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| 4/14/26 | Fewer Reps, More Pipeline: How AI-Native GTM Teams Are Doing More With Less w/ Jason Miller, VP Sales @ Unify✨ | AISales+2 | Jason Miller | Series BUnify+12 | USSF+1 | signal-based sellingbuyer intent+3 | — | 51m 46s | |
| 4/7/26 | How to Reinvent Yourself & The Athlete Mindset Behind Elite Sales Teams w/ Evan Cassidy @ Decagon✨ | reinventionathlete mindset+3 | Evan Cassidy | DecagonSales+10 | Oklahoma CitySan Francisco | AI-native customer supportDecagon+3 | — | 58m 52s | |
| 3/31/26 | The $1M Salary GTM Role Nobody Qualifies For Yet w/ Jason Gelman, GTM Partner @ Primary VC✨ | Go-to-MarketVenture Capital+2 | Jason Gelman | Go-to-Market techGTM+16 | New York | GTMPrimary VC+3 | — | 1h 04m 02s | |
| 3/24/26 | How The Best CROs Actually Hire Salespeople w/ Kyle Norton, CRO @ Owner.com✨ | CROsales hiring+2 | Kyle Norton | Shopify PlusHubSpot+11 | TorontoSan Francisco+1 | Owner.comShopify+3 | — | 1h 07m 44s | |
| 3/17/26 | My #1 Rep Closed $3.5M & Never Sold A Day In Their Life w/ Ghazi Masood, CRO @ Replit✨ | AIsales+3 | Ghazi Masood | ReplitSEs+6 | Americas | GTMReplit+3 | — | 49m 15s | |
| 3/10/26 | Why Anthropic is The Hottest Company in AI & & How To Use Claude As A Seller w/ Eleanor Dorfman, Head of Industries @ Anthropic✨ | AIgo-to-market strategy+2 | Eleanor Dorfman | ClaudeClaude Code+10 | — | ClaudeAnthropic+3 | — | 56m 43s | |
| 3/3/26 | 11 Traits That Make A Hot Sales Job & How To Avoid Joining A Dud✨ | sales jobscareer advice+1 | — | AnthropicARR+6 | New YorkSF | career trajectorysales role+6 | — | 23m 15s | |
| 2/24/26 | The Art & Science Of Choosing Which Startup To Join & How To Value Your Equity w/ Billy Gallagher, CEO @ Prospect✨ | startup equityinvesting+2 | Billy Gallagher | ProspectKhosla Ventures+12 | — | Khosla VenturesRippling+2 | — | 55m 14s | |
| 2/17/26 | The Best Sales Reps Are Coin Operated & All Roads Lead Back To The Steak Dinner w/ Jack Gashi, VP of Sales @ Avoca✨ | salesAI+3 | Jack Gashi | AvocaCheck+5 | Jersey | coin-operatedsales organization+3 | — | 1h 05m 28s | |
| 2/10/26 | The Words You Use Are Killing Your Trust & What Great Sellers Do Instead W/ Sam Berg, VP of Sales @ Tennr” | Sam’s BackgroundSam Berg is the VP of Sales at Tennr, one of the fastest-growing companies in the healthcare AI space.Sam leads Tennr’s sales org during a period of hyper-growth, where he’s laser-focused on building disciplined sales teams while scaling a high-trust sales motion.Before Tennr, Sam spent nearly 8 years at VTS (formerly Hightower), where he rose from individual contributor to sales leader, helping to scale an enterprise sales org selling into commercial real estate brokers. Like many other great sales leaders, his career had a seemingly innocuous start: selling tickets to New York Islanders games and building a customer-first sales approach in the process.Sam builds sales teams and systems that scale by earning trust, not burning it.Discussed In This Episode• From $8/hour ticket sales to VP of Sales - how early habits compound• Why discipline and curiosity matter more than talent (and how he actually tests for them in interviews)• His sales interview philosophy: preparation > polish• The competency framework he built to promote SDRs into enterprise reps• Why great sellers sound calm by using trust signals• Transparency breaks patterns - how setting negotiation guardrails builds trust• Why he avoids words like “deal” and “feedback” and how language subtly shapes buyer behavior• How to find the real urgency that accelerates enterprise deals• Why creating context beats jumping to discovery• Why competition fuels the best sales teams pushing to out-execute each otherTimestamps(00:00) Intro, Brooklyn vs. Long Island debate & why food opinions matter more than sales titles(05:00) From club promoting to ticket sales: getting paid $8/hour and taking “small” sales seriously(10:00) Early account research hacks & learning willingness-to-pay the hard way(16:00) “I don’t want to sell glass seats. I want to buy them”: deciding to leave sports for software(21:00) Breaking into software sales, early career mistakes & choosing the small pond over the big logo(27:00) Selling outcomes vs. features: the inflection point that changed how he sold forever(33:00) Transparency as a sales weapon: naming weaknesses, breaking patterns & earning trust(39:00) Internal vs. external change: what actually creates urgency in enterprise sales(45:00) From Hightower to Tennr: why vertical, “unsexy” industries are the best place to sell(50:00) Joining Tennr early: hypergrowth energy, imposter syndrome & “Hamilton-level” intensity(55:00) Building a sales team from scratch: why discipline and curiosity beat raw talent(01:01:00) How he interviews sellers: testing preparation, hypotheses & real curiosity(01:07:00) Tone, cadence, and posture: why great sellers sound calm instead of clever(01:12:00) Words that kill trust (“deal,” “feedback”) and what to say instead(01:17:00) Healthy sales competition: winning on execution, not hoping teammates failAbout The Vibescaling PodcastThe Vibescaling podcast interviews GTM leaders and investors at top AI startups and early-stage companies.Every week, host Chris Balestras, partner @ Vibescaling (an advisory, recruiting, investing, & media firm for seed through series C AI-natives) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today.No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.About VibescalingVibescaling is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.Where to Find VibescalingLinkedIn: www.linkedin.comYouTube: YouTubeVibescaling PodcastNewsletter: Chris from vibescalingHome | Vibescaling BlogWebsite: https://www.vibescaling.ai/ | — | ||||||
| 2/3/26 | Why You Should Join Cursor Over OpenAI and Anthropic & How To Avoid Bad Sales Hires W/ Tomer Chernia, VP of GTM @ Cursor | Tomer Chernia is the VP of GTM at Cursor, one of the fastest-growing companies in tech - reportedly going from 0 to $500M+ ARR faster than almost any company in history.Before Cursor, Tomer spent three years at Vercel where he helped build out the go-to-market motion and developed their GTM efficiency framework. Prior to that, he was at Branch and Segment as early GTM hires.Tomer got his start in tech at Yahoo, then joined Wildfire pre-acquisition by Google - where he caught the startup bug. He even tried his hand at founding a company before going back to sales.He's a serious foodie (ask him for SF restaurant recs) and recently got into natural wine.Discussed In This Episode• His interview process evolution: from "pitch your product" to discovery sessions + deal reviews• The "three hows" technique for testing candidate depth until their understanding breaks• How Cursor went from 8 GTM people to nearly 100 in six months• Why he chose Cursor over staying at Vercel (the "would you regret it?" test)• The Cursor vs. OpenAI/Anthropic pitch for candidates - why "born adult" matters• Why Cursor pays commissions when others don't - the real tradeoffs• PLG sellers vs. top-down sellers - different strengths, different failure modes• Why sales morale matters more than most leaders admit - and how quota setting destroys it• "Buyers are liars" - why your champion isn't always a reliable narrator• The future of outbound: signal-based, not spray-and-prayTimestamps(00:00) Intro & SF Restaurant Recommendations from a Serious Foodie(04:00) From Humanities Major to Yahoo: How Tomer Fell Into Sales by Accident(12:00) Wildfire, Google, Founding a Company & Why He Went Back to Sales(20:00) The Tap on the Shoulder from Cursor: "Would You Regret Saying No?"(26:00) How to Actually Hire Great Salespeople: Discovery Sessions + Deal Reviews(32:00) The "Three Hows" - Testing Candidate Depth Until Understanding Breaks(38:00) Why Sales Morale Matters: Quota Setting & Rep Motivation(44:00) Cursor's GTM Growth: From 8 People to Nearly 100 in Six Months(50:00) Why Cursor Over OpenAI or Anthropic: The "Born Adult" Company(56:00) The Future of Outbound & How to Stand Out as a CandidateAbout The Vibescaling PodcastThe Vibescaling podcast interviews GTM leaders and investors at top AI startups and early-stage companies.Every week, host Chris Balestras, partner @ Vibescaling (an advisory, recruiting, investing, & media firm for seed through series C AI-natives) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today.No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.About Vibescaling:Vibescaling is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.Where to Find Vibescaling:LinkedIn Company Page - https://www.linkedin.com/company/vibescaling/YouTube - https://www.youtube.com/@vibescalingNewsletter -https://www.vibescaling.blog/Website -https://www.vibescaling.ai/ | — | ||||||
| 1/28/26 |  Jack Dorsey Hired Me from My Dorm Room As Employee 100 @ Square | Mike Donahue, CRO @ Maven AGI | Episode Description:Mike Donohue is the CRO at Maven AGI, one of the fastest-growing AI agent companies focused on customer support automation.Before Maven, Mike was SVP of Sales at Gubshup, a messaging AI tool, and spent time at PayPal to give BigCo a spin.He was an early sales hire at Lean Plum, growing with the company from Series A through Series D and competing head-to-head with Braze during the mobile marketing wars.Mike's career started unconventionally - while captain of the varsity heavyweight rowing team at Columbia, he ran a dorm business doing room cleaning, dry cleaning, and beverage delivery. He started using Square to process payments, fell in love with the product, and eventually got hired directly by Jack Dorsey when the company was sub-100 employees.He's a Philly native who will tell you Tony Luke's beats Pat & Geno's as the best cheesesteak in Philly.Discussed in this episode:Why sales is a science, not an art - and why hiring "artists" at scale doesn't workThe interview question that reveals how candidates actually use AI: meh, good, and great answersHow Mike went from running a dorm business at Columbia to getting hired by Jack Dorsey at SquareThe athlete mentality in sales and why "the score takes care of itself"Where AI agents are actually delivering ROI in customer support todayThe Braze vs. Lean Plum horse race: what competing from Series A to C taught him about GTMWhy sales dinners are dead and education-first selling is the new playbookHow to stand out when reaching out for a job (hint: it's not just a LinkedIn DM)Why the best salespeople are building with AI tools like Claude and Windsurf, not just using ChatGPT for interview prepEpisode Timestamps:(00:00) Intro & Best Philly Cheesesteak: Why Tony Luke's Beats Pat & Geno's(04:00) Running a Dorm Business at Columbia & Discovering Square(08:00) Getting Hired by Jack Dorsey When Square Was Sub-100 Employees(12:00) The Athlete Mentality in Sales: "Score Takes Care of Itself"(18:00) Why Sales is a Science, Not an Art - Playbooks Beat Artists(24:00) How to Evaluate AI Usage in Sales Interviews: Meh, Good & Great Answers(30:00) "I Vibe Coded 80% of My Outbound in Windsurf" - What Impresses Hiring Managers(38:00) Where AI Agents Are Actually Working in Customer Support(45:00) The Braze vs Lean Plum Horse Race: Competing from Series A to C(52:00) Why Sales Dinners Are Dead & Education-First Selling is Winning(58:00) Maven AGI is Hiring - What Mike Looks For in CandidatesAbout The Vibescaling Podcast:The Vibescaling Podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Vibescaling (an advisory, recruiting, investing, & media firm for seed through series C AI-natives & SaaS startups) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today. No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.About Vibescaling:Vibescaling is an advisory, recruiting, media, & investing firm for seed through series C AI-natives & fast-growing SaaS startups scaling from 0 to $100M ARR.Where to Find VibeScaling:WebsiteLinkedIn Company PageYouTubeNewsletter | — | ||||||
| 1/22/26 |  How I Built Legora's GTM Motion To A $1B+ Valuation w/ Patrick Forquer, SVP Global Revenue @ Legora | Episode Description:Patrick Forquer is the SVP of Global Revenue at Legora, one of the leading players in the AI-native legal tech space, coming off a recent Series C raise to value the company at over a billion dollars.Before Legora, Patrick spent 7 years at Braze (formerly AppBoy) from the early days through IPO, leaving as the AVP of sales. He started his career as a BDR at Yext during the 2008 financial crisis, worked at Intralinks, then moved to Cloud Sherpas, managing their Google Cloud relationship before the Accenture acquisition. He was also CRO at Jacquard, an early generative AI company.Pat is one of the more down-to-earth people I've met in the space; I really enjoyed the conversation + hope you do too.Discussed in this episode:Why selling AI is fundamentally different than selling SaaSThe "last mile problem" in vertical AI and why deployment is where deals are won or lostHow deal velocity has accelerated - buyers are moving faster and expect sellers to keep upWhy MEDDICC is not a sales process and how discovery has evolvedThe false tension between PLG and enterprise salesWhat Chris Degnan's book "Make It Snow" reveals about Snowflake's counterintuitive GTM & why they admire itWhy the best time to be a seller is right nowEpisode Timestamps:(00:00) Intro & Pat's Background(02:30) Meeting His Wife at Memory Motel in Montauk(04:30) His Path: From BDR at Yext to SVP of Global Revenue at Legora(06:50) Selling SaaS vs AI: Why It's the Best Time to Be a Seller(12:00) The Last Mile Problem in Vertical AI Sales(18:00) How Deal Velocity Has Changed with AI(26:00) Discovery, Change Management & Why MEDDICC Isn't a Sales Process(34:00) Chris Degnan's "Make It Snow" and Snowflake's GTM Playbook(42:00) PLG vs Enterprise: The False Tension(55:00) Basketball Talk: Jalen Brunson, the Knicks & NYC Sports(58:00) Creative Ways to Break Through & Get a ResponseAbout The Vibescaling Podcast:The Vibescaling Podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Vibescaling (an advisory, recruiting, investing, & media firm for seed through series C AI-natives & SaaS startups) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today. No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.About Vibescaling:Vibescaling is an advisory, recruiting, media, & investing firm for seed through series C AI-natives & fast-growing SaaS startups scaling from 0 to $100M ARR.Where to Find VibeScaling:WebsiteLinkedIn Company PageYouTubeNewsletter | — | ||||||
| 1/15/26 |  How I Broke Into VC From Sales With Liam Mulcahy, Operating Partner @ Kleiner Perkins | Episode Description:Liam Mulcahy is an Operating Partner at Kleiner Perkins, where he leads go-to-market strategy for their portfolio companies from Series A through C.Before Kleiner, Liam was an early member of the GTM ops team at Unusual Ventures where he served as the first sales rep for 26+ portfolio companies simultaneously, building their GTM motions from zero.He cut his teeth at MongoDB pre and post-IPO, where he went from being told "we don't think you can cut it" to becoming a top performer and sales leader.Liam is one of the most thoughtful and intelligent voices on zero-to-one sales, career strategy, and what it actually takes to break into venture capital from an operating background.Discussed in this episode:The cardboard cutout Hail Mary that landed Liam his job at MongoDBWhy you should treat interviewing like a sales dealThe "MBA in sales" - why MongoDB's training was more valuable than business schoolCold calling the Midas List to break into VC without an MBAHow Kleiner Perkins rebuilt their operating team with peak-career subject matter expertsWhy a signed contract is now your best competitive differentiatorThe three rings of outbound: warm network, lukewarm, and ice coldStep-by-step guide to breaking into VC from a sales background"Effort is free" - why some people are stuck in third gearWhat Liam would tell someone who says "I want your job" & how to break into VC from salesEpisode Timestamps:(00:00) Liam's Journey: From D1 Track Athlete to Kleiner Perkins Operating Partner(06:00) Why Advertising Taught Him Sales (Without Realizing It)(10:00) The Tim Ferriss Books That Sparked the Startup Bug(14:00) What Made MongoDB's Interview Process Hard (In A Good Way)(18:00) The Cardboard Cutout That Changed Everything(24:00) Treat Your Interview Like a Deal: Getting Feedback After Rejection(31:00) Dealing With Imposter Syndrome(36:00) "If You're Going to Do Something, Do It Well" - The Flashcard QBR Story(40:00) Why Liam Didn't Want to Be a CRO(45:00) Cold Calling the Midas List to Break Into VC(50:00) How Kleiner Uniquely Positions The VC Operating Model(57:00) Why a Signed Contract is Your Best Competitive Moat(62:00) How to Actually Break Into VC (Step by Step)About The Vibescaling Podcast:The Vibescaling Podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Vibescaling (an advisory, recruiting, investing, & media firm for seed through series C AI-natives & SaaS startups) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today. No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.About Vibescaling:Vibescaling is an advisory, recruiting, media, & investing firm for seed through series C AI-natives & fast-growing SaaS startups scaling from 0 to $100M ARR.Where to Find VibeScaling:WebsiteLinkedIn Company PageYouTubeNewsletter | — | ||||||
| 1/8/26 |  From $2M to $950M ARR: How Kyle Parrish Built Figma's Sales Machine - Vibescaling Podcast Episode #3 | Episode Description:Kyle Parrish was the third sales hire at Dropbox and the founding sales leader at Figma, where he scaled the business from $2M to $950M in ARR over six and a half years through their IPO.Before Figma, Kyle opened Dropbox's Austin office and hired 150 people in under two years. He's now advising and investing in top AI-native startups.Kyle is one of the most thoughtful go-to-market leaders in the game - his frameworks on PLG-to-enterprise, founder-led sales, and building high-performing teams are pure gold.Also, shout out to our awesome sponsor for this episode, Kondo. Think of it like Superhuman for LinkedIn messages - if you're terminally on LinkedIn like I am and your inbox is becoming unwieldy, give it a try for the first month free using this link - it saves me over an hour a day.Discussed in this episode:How Kyle spotted Figma before anyone else: the three trends that signaled a breakoutWhy PLG companies should consider hiring top-down enterprise sellers, and sometimes not "PLG sellers"The real reason early customers buy: they're betting on the founder and the dream, not the productWhen founders should hire a head of sales vs. starting with individual repsOpening Dropbox Austin: hiring 150 people in under two years and building the GTM hub from scratchThe founder-led sales trap: why pitching too early kills deals"Stay low at the highs, high at the lows": how to survive the emotional roller coaster of startupsWhat most founders get wrong about discovery (and why three boilerplate questions won't cut it)Building your network like a bonsai tree: intentional cultivation over years, not transactional asksWhy the best early-stage sellers are "evangelical" - and what that actually looks likeThe FOMO trap: why comparing yourself to companies on a sugar high will wreck youWhat Kyle would tell his younger self after 15 years in startups: stress out less, the score takes care of itselfEpisode Timestamps:(00:00) Kyle's Journey: From Dropbox's Third Sales Hire to Figma's Sales Leader(06:00) When Should Founders Hire Their First Head of Sales?(12:00) The Hardest Part of Founder-Led Sales Transition(18:00) PLG to Enterprise: Why You Might Want the Top-Down Seller(24:00) Building Dropbox Austin: 150 Hires in Under 2 Years(30:00) How Kyle Spotted Figma Before Anyone Else (The 3 Trends)(36:00) Scaling Figma from $2M to $950M ARR(42:00) "Stay Low at the Highs, High at the Lows" - Surviving the Roller Coaster(48:00) Why Founders Pitch Too Early (The Discovery Trap)(53:00) What Kyle Would Tell His Younger SelfAbout The Vibescaling Podcast:The Vibescaling Podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Vibescaling (an advisory, recruiting, investing, & media firm for seed through series C AI-natives & SaaS startups) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today. No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.About Vibescaling:Vibescaling is an advisory, recruiting, media, & investing firm for seed through series C AI-natives & fast-growing SaaS startups scaling from 0 to $100M ARR.Where to Find VibeScaling:WebsiteLinkedIn Company PageYouTubeNewsletter | — | ||||||
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