Vibescaling Podcast

Why The Best Sales Rep You Interview Is Probably Your Worst Hire with Mike Heller, Partner @ Floodgate

Mike’s Background Mike 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 job Timestamps (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 Code 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) 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: https://www.linkedin.com/company/vibescaling/ [https://www.linkedin.com/company/vibescaling/] YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg [https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg] Newsletter: https://www.vibescaling.blog/ [https://www.vibescaling.blog/] Website: https://www.vibescaling.ai/ [https://www.vibescaling.ai/]

How We Built Profound’s GTM Motion To A $1B+ Valuation w/ Mark Ebert, SVP of Revenue @ Profound

Mark’s Background Mark 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 Episode Why enablement teams shouldn't actually be running enablement and who should instead when product ships daily The two questions every new AE at an AI-native company should be obsessed with answering in week one The "leave them alone on the sales floor" test for spotting a sales leader who's actually a doer vs. a dashboard leader Why he'd rather hire the rep who crushed it at the #3 product company than the rep who hit 150% at the obvious category leader What World War 2 battle planning teaches him about running a POC The "see the movie before it plays" framework and how the best reps whiteboard the 3 most likely deal paths and pre-plan their counter-moves Why 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 itself The Jolt Effect: why most deals die from fear of screwing up, not fear of cost and how to surface that fear before the buyer does AI 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 overnight Timestamps: (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 Effect 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) 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: https://www.linkedin.com/company/vibescaling/ [https://www.linkedin.com/company/vibescaling/] YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg [https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg] Newsletter: https://www.vibescaling.blog/ [https://www.vibescaling.blog/] Website: https://www.vibescaling.ai/ [https://www.vibescaling.ai/]

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 dominate Timestamps 00:00 - Cold Open: Why Finance is Deterministic and AI Isn't 01:24 - Intro & James's Origin Story: Stock Picking at CompUSA 03:42 - Breaking Into Tech Sales at Pure Storage 06:34 - Apple, Morgan Stanley & Choosing the Startup Path 08:23 - Joining Sentieo & Selling to Hedge Funds 11:15 - Why Selling AI is Different from Selling SaaS 12:31 - Solving for Hallucinations in High-Stakes Finance 15:18 - Why MDs Are Surprisingly Heavy AI Users 17:24 - Structuring Rogo's Enterprise GTM Team 20:57 - Why Bankers Make Great Salespeople (The Renaissance Thesis) 22:41 - "AI for Finance" is Meaningless: Why Rogo Picked IB 26:01 - Why Anthropic Won't Eat the App Layer 31:14 - Defining the AI-Native Seller 34:33 - Building a Sales Team from Burned-Out Junior Bankers 39:07 - The Chainsmokers' Alex Pall: Rogo's Best SDR 42:16 - Reimagining GTM Workflows with AI 45:38 - What Rogo is Hiring For 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) 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: https://www.linkedin.com/company/vibescaling/ [https://www.linkedin.com/company/vibescaling/] YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg [https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg] Newsletter: https://www.vibescaling.blog/ [https://www.vibescaling.blog/] Website: https://www.vibescaling.ai/ [https://www.vibescaling.ai/]

The Old Sales Playbook Is Dead: Hiring + Selling In The AI Era w/ Jacquelyn Goldberg, VP Sales @ Unframe AI

Jacquelyn's Background Jacquelyn 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 Career About 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 Vibescaling LinkedIn: https://www.linkedin.com/company/vibescaling/ [https://www.linkedin.com/company/vibescaling/] YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg [https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg] Newsletter: https://www.vibescaling.blog/ [https://www.vibescaling.blog/] Website: https://www.vibescaling.ai/ [https://www.vibescaling.ai/]

Tell Them the Movie Before They Watch It: Enterprise Sales, Champion Building & the No-Pilot Stance W/ Adam Ali, SVP Revenue @ Rox

Adam Ali's Background Adam Ali is the SVP of Worldwide Revenue at Rox, an AI-native revenue operating system backed by Sequoia, GV, and General Catalyst. He joined in September 2025 after being named Glean's Top Sales Leader of 2025 and leading the entire company in total revenue growth, net new enterprise logos, and time to productivity per rep. Before Glean, Adam spent six years at Rubrik, joining when the company was at $20M ARR and helping scale to over $700M ARR. Before that, he got in his early reps at SAP, where he was #1 in the sales academy every week. Unlike most people in sales, Adam didn't fall into it. He started the sales program at the University of Arizona before graduating and was prospecting his way into jobs as a student. Discussed In This Episode • Why Adam knew he wanted to be in sales before he ever graduated and what made him so intentional about it from day one • The $100 bill story: what Rubrik's founder taught him about human capital and why it changed his career • His "test first, build second" philosophy on champion building and why being on a texting basis isn't the signal you think it is • The difference between a champion and a coach • Shadow selling: what actually happens between meetings that separates great reps from everyone else • His no-pilot stance: why EB go/no-go alignment matters more than any POC • "Tell them the movie before they watch it" and how to run a proof of value that actually closes • Breaking the deal: why asking for the business early is the fastest way to find out what's real • Executive presence training and what it taught him about stillness, eye contact, and body language • How Rox fits into the AI sales tech landscape and why he believes pre-built agents win over custom builds Timestamps (00:00) Intro & Adam's Background (02:08) Being Sales-Pilled Before Graduation: Starting the Sales Program at U of A (06:02) Landing at SAP & What Big Company Sales Actually Teaches You (07:33) Executive Presence Training: Stillness, Eye Contact & Body Language (09:58) The Manager Who Left for Rubrik & Planting the Seed (14:40) The $100 Bill Story: Human Capital & Getting in the Game (18:56) Champion Building: Test First, Build Second (22:01) The Difference Between a Champion and a Coach (23:35) Shadow Selling: What Happens Between the Meetings (25:53) How to Test Whether Someone Is Actually Your Champion (29:14) The No-Pilot Stance: EB Go/No-Go and Proof of Value (36:17) Tell Them the Movie Before They Watch It (38:37) How to Build Momentum Inside a Single Meeting (41:04) Breaking the Deal: How to Find Out What's Really Going On (45:33) Rox, AI Sales Tech & Where the Landscape Is Heading (51:57) What an Agent Swarm Actually Means (57:35) Why Adam Made Two Bets on AI Companies (1:00:35) How to Get Hired at Rox About 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 Vibescaling LinkedIn: https://www.linkedin.com/company/vibescaling/ [https://www.linkedin.com/company/vibescaling/] YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg [https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg] Newsletter: https://www.vibescaling.blog/ [https://www.vibescaling.blog/] Website: https://www.vibescaling.ai/ [https://www.vibescaling.ai/]