Vibescaling Podcast

Vibescaling
  • 5.0 (6)
  • TECHNOLOGY
  • UPDATED WEEKLY

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 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. Find us @ https://www.vibescaling.ai/ & https://www.vibescaling.blog/

  1. 1D AGO

    11 Traits That Make A Hot Sales Job & How To Avoid Joining A Dud

    This week, Chris goes solo. No guest necessary as he breaks down the answer to the question he’s gotten asked more times than he can count: how do I actually choose the right sales job? Chris has spent several years navigating this himself, written articles on it, and interviewed enough VPs of Sales and CROs to know what separates career-defining moves from ones that stall your career trajectory without you even realizing it. The result? His 11 traits framework, which is a crystal clearest distillation of what makes a sales role genuinely great. Discussed In This Episode • The #1 thing the happiest, most successful people in Chris's network all have in common, and why most people make the mistake of not prioritizing it • GTM mafias and talent vortexes: why 90% of the time, the people landing the best jobs have a champion on the inside • Why OpenAI and Anthropic are career insurance, and what that snowball effect actually looks like in action • The "breakout period" of the Series A through C sweet spot that startup veterans optimize for, and why the AI natives have blown up the old ARR benchmarks • The inbound tailwind test: if more than 30% of deals are outbound, what that signals about the environment you're walking into • Why some of Chris's friends joined PLG companies with tons of inbound but still hated the job • The path-to-enterprise question every seller needs to ask before signing an offer, and why $100K deal size is the minimum bar he'd set • Selling complex products vs. app layer and why Chris wishes he'd gone more technical earlier • What "AI native" sales leadership actually looks like vs. the dinosaur playbook • Why in-person matters in the AI era, and the Keith Rabois framing that explains the feedback loop advantage • How to do due diligence on engineering shipping velocity before you join, and why it directly affects your close rate as an AE • Back channeling the right way: who to actually talk to, why VCs don't know what you need to know, and why Repview has its limits Timestamps (00:00) Why Chris Is Going Solo For This Episode (02:22) Trait #1: Join a Mafia or a Talent Vortex (04:45) Trait #2: Clear Signs of Market Pull Via the Inbound Tailwind Test (06:15) Trait #3: The Breakout Period Explained: Find the Risk-Reward Sweet Spot (08:00) Trait #4: Does the Product Have a Path to Enterprise? The $100K Deal Question (10:30) Trait #5: Why Actual Interest in the Industry and Problem is a Prerequisite to Sell Well (11:30) Trait #6: Why Technical Sales Compounds Your Career (13:30) Trait #7: The Ability to Do More Than Just Sell at an Early-Stage Startup (15:00) Trait #8: Sales Leadership Must Be AI Native (and What That Actually Means) (17:30) Trait #9: New York and/or SF Presence and the Case for the In-Person Feedback Loop (19:45) Trait #10: The Engineering Team Needs to Be Shipping Constantly and How to Test Them (21:30) Trait #11: Back Channel Everything: Who to Talk To and Who to Skip (23:30) Recap of All 11 Traits & What's Coming Next on Vibescaling 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/ YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg Newsletter: https://www.vibescaling.blog/ Website: https://www.vibescaling.ai/

    23 min

  2. FEB 24

    The Art & Science Of Choosing Which Startup To Join & How To Value Your Equity w/ Billy Gallagher, CEO @ Prospect

    Billy’s Background Billy Gallagher is the founder and CEO of Prospect, a robo-advisor that helps startup employees better manage their private company equity. Think: Wealthfront for startups. Before Prospect, Billy was on the investing team at Khosla Ventures, where he worked on early-stage deals from seed through Series B, including companies like Stripe, DoorDash, and Instacart. He then joined Rippling as the 34th employee in a generalist "special projects" role, staying for three and a half years as the company scaled to over a thousand people. Between Khosla, Rippling, a Stanford MBA, and a stint covering startups at TechCrunch, he's seen the startup equity problem from literally every seat at the table The gap he kept seeing between how professional investors managed equity at Khosla vs. how employees fumbled through it at Rippling is exactly what led him to start Prospect. Timestamps (00:00) Intro & Billy's path from Khosla Ventures to Rippling to founding Prospect (03:44) How to evaluate a startup quantitatively: investors, headcount, web traffic (05:14) Why the lead investor's seniority level matters more than the firm name (07:14) Tracking investor quality across rounds (and when it's a red flag) (09:17) The rise of the solo GP and what it signals for employees (10:18) Second-time founders vs. first-time founders: when experience is an edge (12:10) The Ramp example: hitting a double, staying hungry, then hitting a grand slam (13:27) Tools for researching startups: Prospect, Crunchbase, and what to look for (17:30) Headcount growth as a proxy for business growth (19:54) Secondary market signals: what they tell you about a company between rounds (22:14) When a fundraising gap is a red flag vs. a sign of capital efficiency (24:46) The breakout period: why Series A–C is the best risk-adjusted time to join (30:23) Qualitative signals: founder vision, speed, and the talent vortex (32:07) How to spot a fast-moving founder without asking a single question (34:00) Talking to customers: developing taste for product-market fit (36:42) Market timing and the Paul Graham test: it should feel almost too late (39:53) Equity 101: options vs. RSUs and when you'll get each (41:50) QSBS and early exercise: the tax advantages most employees miss (43:59) Post-termination exercise windows: why 90 days is no longer acceptable (47:38) Percent ownership: how to benchmark your equity offer (49:23)Tender offers and the 20% rule: taking chips off the table without losing upside (52:24) What Prospect does and how to use it to navigate your equity lifecycle 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/ YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg Newsletter: https://www.vibescaling.blog/ Website: https://www.vibescaling.ai/

    55 min

  3. FEB 17

    The Best Sales Reps Are Coin Operated & All Roads Lead Back To The Steak Dinner w/ Jack Gashi, VP of Sales @ Avoca

    Jack's Background Jack Gashi is VP of Sales at Avoca, an AI-native platform bringing automation to home service businesses. At Avoca, Jack is building the sales organization from scratch as the company scales AI-driven voice and scheduling technology across industries. Before Avoca, Jack spent several years at Check, a high-growth cybersecurity startup, where he learned what it actually takes to build durable GTM teams. Prior to that, he worked in ad sales at Foursquare during the company’s peak growth years, and even earlier in his career Jack cut his teeth in classic boiler-room sales at Yext, making hundreds of cold calls a day selling into home services. Through experience across SMB, mid-market, and enterprise sales, Jack knows what it actually takes to build a sales org that works. His philosophy is rep-first and unapologetic: sales is coin-operated, built on trust, and keeps the lights on. He’s a proud Jersey guy, a former Fyre Festival attendee (yes, really), and the first to admit that the best sales conversations still happen face-to-face. Discussed In This Episode • Why fear-based sales cultures break down while trust-first cultures actually scale • Jack’s early career in boiler-room sales (150 cold calls a day) and why that foundation still matters • How tech sales talent evolved from “falling into it” to Ivy League grads choosing it deliberately • The “trough of disillusionment” every sales career hits • Why sales is coin-operated and why pretending money doesn’t matter creates misalignment • The hidden, spreadsheet-level cost of losing a $2M ARR top rep • How to spot whether sales is a first-class citizen or a “necessary evil” at a company • Why PLG works… until it doesn’t • How real trust gets built (hint: it’s not five-step cadences) • Why great AEs sell their own job search like a deal • What sales skills transfer to real life Timestamps (00:00) Why fear-driven sales cultures fail — and what actually builds trust (03:29) Fyre Festival and the danger of believing the outside story (06:03) 150 cold calls a day at Yext and learning to really sell (09:28) How tech sales talent has changed — Ivy League grads choosing sales (15:03) The “trough of disillusionment” in a sales career (18:19) Stop romanticizing work (21:26) Sales morale as the beating heart of a company (23:09) How to tell if a founder truly respects sales (25:03) The real cost of losing a top rep (26:11) “All roads lead back to steak dinners” — the limits of PLG (29:00) Sales as trust transfer, not scripts (31:02) Why automation and perfect sequencing keep failing (33:04) Product knowledge as a trust weapon (36:31) When to leave a good job — why Jack chose Avoca (44:15) How elite AEs evaluate roles when data doesn’t exist (46:06) Are the best reps coin-operated? (53:41) What’s dead in modern sales 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 Company Page - https://www.linkedin.com/company/vibescaling/ YouTube - https://www.youtube.com/@vibescaling Newsletter - https://www.vibescaling.blog/ Website - https://www.vibescaling.ai/

    1h 5m

  4. FEB 10

    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 other Timestamps (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 fail 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 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: www.linkedin.com​ YouTube: YouTubeVibescaling Podcast​ Newsletter: Chris from vibescalingHome | Vibescaling Blog​ Website: https://www.vibescaling.ai/

    1h 6m

  5. FEB 3

    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-pray Timestamps (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 Candidate 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 Company Page - https://www.linkedin.com/company/vibescaling/ YouTube - https://www.youtube.com/@vibescaling Newsletter - https://www.vibescaling.blog/ Website - https://www.vibescaling.ai/

    58 min
  6. Jack Dorsey Hired Me from My Dorm Room As Employee 100 @ Square | Mike Donahue, CRO @ Maven AGI

    JAN 28

    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 prep Episode 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 Candidates 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

    1h 1m
  7. How I Built Legora's GTM Motion To A $1B+ Valuation w/ Patrick Forquer, SVP Global Revenue @ Legora

    JAN 22

    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 Response 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

    1h 2m
  8. How I Broke Into VC From Sales With Liam Mulcahy, Operating Partner @ Kleiner Perkins

    JAN 15

    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

    1h 9m
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Ratings & Reviews

5
out of 5
6 Ratings

About

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 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. Find us @ https://www.vibescaling.ai/ & https://www.vibescaling.blog/

Information

  • Creator
    Vibescaling
  • Years Active
    2025 - 2026
  • Episodes
    13
  • Rating
    Clean
  • Copyright
    © Vibescaling
  • Show Website
    Vibescaling Podcast

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