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The Crew Podcast

by Crew

The Crew Podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, co-founder @ Crew (a GTM recruiting, media, & investing firm for seed through series D 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.withcrew.ai/ & https://www.withcrew.blog/

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Episodes

  1. Why Most AI Startups Aren't Defensible & Why Sales Teams Fail w/ Brendon Cassidy, Founding GTM @ LinkedIn

    Brendon Cassidy is the founder of Cassidy Ventures, where he operates, advises, and invests in startups, helping founders with everything from demand and pipeline to their first VP of Sales hire. He was one of LinkedIn's earliest employees, then ran sales at EchoSign alongside Jason Lemkin…

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  2. Cyber Risk Has Never Been Higher & Selling Cyber 101 w/ Steve Pascucci VP of Global Sales @ Outtake

    Steve Pascucci is VP of Global Sales at Outtake, the Series B, AI-native security company building a trust layer for the internet. Backed by CRV and ICONIQ and recently named a Forbes Next Billion-Dollar Startup, Outtake protects the world's most recognizable brands and executives from...

  3. Live Podcast: The GTM Rebrand, CRO Musical Chairs & Talent Mafias @ Reserve Padel NYC

    Live from Hudson Yards: Crew's first-ever live podcast, recorded at the AI GTM Paddle Club Event at Reserve with roughly 150 of New York's best GTM operators in the room. Crew's twelfth event in two years, and the first one on a padel court. The Panel Chris Balestras, Partner at Crew, hosting....

  4. GTM Roundtable: The State of AI-Native Sales w/ Clay, Parallel, Avoca & Profound

    Four sales leaders running revenue at AI-native companies sat down with Chris Balestras to talk about what the job actually looks like right now. Territory plans that get thrown out mid-year. Comp models nobody has figured out. And the thing candidates never hear before they sign, which is that…

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  5. The Science of Sales + Why Founders Hire Sales Too Early w/ Mark Roberge, Stage 2 Capital

    Mark Roberge is co-founder and Managing Director at Stage 2 Capital, a VC firm backed by roughly a thousand LPs who are go-to-market operators, including the founding CRO of Snowflake and revenue leaders at Anthropic, OpenAI, Databricks, and GitHub. He was the fourth hire at HubSpot and its CRO,...

  6. Building GTM Agents Live + The AI-Pilled AE Operating System w/ Nic Siegle, Founding AE @ Dust

    Nic's Background Nic Siegle is a founding account executive at Dust, the Series B, Sequoia-backed platform for teams of humans and teams of agents. He has been there about a year, placed by Crew's recruiting practice, and came in from a product-led background at Mixpanel and Asana, where product...

  7. The 0 to $20M GTM Traps + How To Diligence A Founder w/ Dini Mehta, Operating Partner @ Peak XV

    Dini Mehta is an Operating Partner at Peak XV, where she parachutes into portfolio companies on go-to-market, sits in exec meetings, runs forecast calls, and hosts open office hours for founders and GTM teams across the portfolio. She was CRO at Lattice, where she took the company from $3M to…

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  8. Why I Left VC To Get Back Into The GTM Operating Seat w/ Liam Mulcahy, Head of GTM @ Parallel

    This week Chris sits down with Liam Mulcahy, Head of Go-to-Market at Parallel Web Systems, who spent seven years in venture at Kleiner Perkins before taking an operating role and bringing seven people with him. Liam's claim is that the innovator's dilemma gap has effectively closed: Parallel has...

  9. Why Utah Produces Elite Sales Talent + Building The GTM Machine @ Exa w/ Marcus Holm, CRO @ Exa

    Marcus Holm is the Chief Revenue Officer at Exa, the search API built for agents, now used under the hood by Cursor and Cognition's Devin among others. He joined in 2026 after nearly four years at LaunchDarkly, where he was CRO and then President and took rep quota attainment from 18% to 54%....

  10. Why Remote Breaks at Scale & the GTM Playbook Behind AI Agents w/ Darren Moffett, VP of Sales @ LangChain

    This week Chris sits down with Darren Moffett, VP of Sales at LangChain, who spent his career building sales orgs at MuleSoft and GitLab before joining LangChain 18 months ago. Darren treats the conversation like an audit of his own first year and a half in the seat: the pricing threshold that...

  11. Inside the GTM Playbooks at Twilio & Vanta w/ Stevie Case, CRO @ Vanta

    Stevie Case is the first CRO at Vanta, the trust management platform, where she's helped scale the business from roughly $20M to past $300M in ARR. Before Vanta, she spent six years at Twilio as it grew from about $200M to $3.5B in revenue and from 500 to 9,000 people, where she absorbed the...

  12. The First Sales Hire Mistake That Sinks Startups w/ Rafa Jara-Simkin, Partner @ Theory Ventures

    Rafa Jara-Simkin is a Partner at Theory Ventures, the research-driven VC founded by Tomasz Tunguz. Before investing, Rafa spent nearly a decade in the GTM trenches. First, he joined Looker as employee ~25 in 2013, and rode it from ~$1M to $100M+ ARR through the Google acquisition, building and...

  13. 12 Things That Top Candidates Are Doing To Land Offers in 2026 w/ Chris Balestras, Co-founder @ Crew

    This week's episode runs Chris's usual solo listicle format, but he's not flying solo this time. Instead, he's joined by Matt Roberts, Crew's first hire and the operator running its BDR and SDR search, for a rapid-fire breakdown of the 12 things that separate the candidates who land sales offers…

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  14. How We're Scaling Vercel's GTM Motion Through A 9B Valuation w/ Nick Bogaty, CRO @ Vercel

    Nick Bogaty is the CRO at Vercel, and he got there on one of the least linear paths in enterprise software. He spent roughly a decade in open source, including helping create the book file-format standard behind modern e-readers, and then ran product teams at Adobe. He moved into go-to-market at...

  15. How Clay Built the GTM Team Behind a $5B Valuation w/ Becca Lindquist, Head of Sales @ Clay

    Becca Lindquist is the Head of Sales at Clay, the go-to-market infrastructure platform that's grown past nine figures and become one of the most loved tools in modern sales. Before Clay, she spent four-plus years at dbt Labs, where she joined at roughly $600K in committed revenue (three reps, no...

  16. Why Product Love Doesn't Actually Close Deals w/ Simran Duggal, VP of Sales @ Juicebox

    Simran Duggal is VP of Sales at Juicebox, an AI-native recruiting platform where she leads GTM across three functions and 18 direct reports. She spent five years at Webflow as one of its early enterprise reps, building an enterprise motion on top of a product-led base, and came up before that in...

  17. Don't Take the Anthropic Job First w/ Mark Goldberger, VP Sales @ Metaview

    New episode of the Crew Podcast with Mark Goldberger (VP of Sales at Meadowview, the AI-native recruiting platform). Mark's career is the dictionary definition of the non-obvious path: sommelier tasting 5,000 wines a year → bootstrapped a big-data startup in 2009 → 100 job applications with zero...

  18. How To Pick The Right AI Company To Bet On & Operationalize Champion Building w/ Bryan Cox, VP of Worldwide Sales @ Braintrust

    Bryan Cox is the VP of Worldwide Sales at Braintrust, the eval and observability platform that builders and frontier model providers alike rely on to ship AI agents. Before Braintrust, Bryan spent nearly five years at Grafana, joining at Series A/B and helping build one of the most respected...

  19. State of GTM Recruiting @ The AI-Natives w/ Chris Balestras, Co-founder @ Crew

    This week, Chris goes solo. No guest necessary as he shares his reaction to a recent 20VC episode where Chad Peets and Chris Degnan sat down with Harry Stebbings to lay out their view of the GTM recruiting landscape. The two dropped roughly 18 claims about hiring, comp, and what’s actually...

  20. Sales Mafias & What Made MongoDB Great w/ Graham Moreno, VP Worldwide GTM @ Parallel

    Graham Moreno is the VP of Worldwide GTM at Parallel Web Systems, where he's building the go-to-market motion for one of the most talked-about AI-native companies in the space. Before Parallel, Graham scaled Windsurf's GTM org from a handful of sellers to a full enterprise machine, serving as...

  21. 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…

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  22. How To Hire Sales Reps Like a Moneyball GM W/ Navid Zolfaghari, Chief Sales Officer @ Zapier

    Navid's Background Navid 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…

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  23. How The Best Salespeople Are Building Agents in GTM w/ Roy Mathew, Head of Sales @ Gumloop

    Roy’s Background Roy 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…

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  24. 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...

  25. How Harvey Scaled GTM to an 11B Valuation w/ Rob Saliterman, VP of Sales @ Harvey

    Rob’s Background Rob 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...

  26. 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...

  27. 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…

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  28. 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...

  29. 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...

  30. 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...

  31. Fewer Reps, More Pipeline: How AI-Native GTM Teams Are Doing More With Less w/ Jason Miller, VP Sales @ Unify

    Jason Miller is the VP of Sales at Unify, a signal-based selling platform helping go-to-market teams connect buyer intent to personalized outreach at scale. Before Unify, Jason spent just over seven years at Monday.com, joining as one of the first 12 US sales hires when the company was almost...

  32. How to Reinvent Yourself & The Athlete Mindset Behind Elite Sales Teams w/ Evan Cassidy @ Decagon

    Evan Cassidy’s Background Evan Cassidy is the VP of Sales at Decagon, the leading AI-native customer support platform. He joined as the company's first sales hire when it was doing less than $2M in ARR. Now? Decagon is valued at $4.5B, and Evan has been instrumental to scaling the GTM org along…

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  33. The $1M Salary GTM Role Nobody Qualifies For Yet w/ Jason Gelman, GTM Partner @ Primary VC

    Jason Gelman’s Background Jason Gelman is a Go-to-Market Operating Partner at Primary Venture Partners, one of the largest early-stage VC firm that just closed its $625 million Fund V (the largest to date) a few days ago, bringing total AUM to ~$1.6B. Before Primary, Jason led Revenue Strategy &...

  34. How The Best CROs Actually Hire Salespeople w/ Kyle Norton, CRO @ Owner.com

    Kyle Norton is the CRO of Owner.com, the all-in-one online presence platform for independent restaurants: think Shopify Plus meets HubSpot, but built specifically for your neighborhood restaurant that’s your go-to for ordering in on a Thursday night. He's taken Owner from $2.5M ARR to $100M in…

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  35. My #1 Rep Closed $3.5M & Never Sold A Day In Their Life w/ Ghazi Masood, CRO @ Replit

    Ghazi’s Background Ghazi Masood is the CRO at Replit, one of the most talked-about companies in the AI era, building what they consider to be the only credible end-to-end vibe coding solution for enterprises. Before Replit, Ghazi was VP of Sales at Retool, where he helped scale one of the most...

  36. Why Anthropic is The Hottest Company in AI & & How To Use Claude As A Seller w/ Eleanor Dorfman, Head of Industries @ Anthropic

    Eleanor Dorfman is the Head of Industries at Anthropic, where she leads enterprise go-to-market for Claude at the epicenter of the AI revolution. Before Anthropic, Eleanor built and scaled GTM teams at some of the most talent-dense companies of the last decade. She started her career at Clever...

  37. 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...

  38. 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...

  39. 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...

  40. 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…

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  41. 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...

  42. 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...

  43. 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...

  44. 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+...

  45. 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…

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  46. This Week In GTM Episode #2 (Featuring Brendan Short of The Signal) - 12/5/25

    Timestamps: (00:00) Intros (04:00) Vercel's AI SDR: Replacing a 10-Person Team with One GTM Engineer (08:00) When Should Founders Hire Their First Salesperson (11:00) "Sales Teams Should Be Indistinguishable from Product Managers" (14:00) What Does "Consultative Selling" Actually Mean? (18:00)…

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  47. This Week In GTM Episode #1 - 11/27/25

    Timestamps: (00:00) Why We Changed Our Name from T2D3 to VibeScaling (12:00) Why Is Everyone Calling Sales "GTM" Now? (17:00) Is Sales an Art or a Science? (22:30) The Viral Giga Story: What to Look For Before Joining a Startup (33:00) How to Evaluate Startup Equity (Shares Outstanding Explained)...

  48. Episode 2: Raphael Parker, CRO @ Mandolin | How He Built Segment's GTM Engine from 0 to $100M

    Episode Description: Raph Parker is Head of Revenue at Mandolin, an AI company transforming healthcare operations. Before Mandolin, Raph was the first go-to-market hire at Segment, helping scale the company from seed to its $3.2B acquisition by Twilio. He then served as Chief Growth Officer at…

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  49. Episode 1: Todd Busler, CEO @ Champify | The 0-1 Sales Playbook & GTM Career Guide

    Episode Description: Todd Busler is the CEO of Champify, a sales intelligence platform helping teams build pipeline through champion and user tracking. Before Champify, Todd was a founding AE at Heap, scaling the company from $300K to $40M in ARR over six years. He started his career as one of…

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ABOUT THIS SHOW

The Crew Podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, co-founder @ Crew (a GTM recruiting, media, & investing firm for seed through series D 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.withcrew.ai/ & https://www.withcrew.blog/

HOSTED BY

Crew

CATEGORIES

technology

Frequently Asked Questions

How many episodes does The Crew Podcast have?

The Crew Podcast currently has 49 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.

What is The Crew Podcast about?

The Crew Podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, co-founder @ Crew (a GTM recruiting, media, & investing firm for seed through series D AI-natives) sits down with operators from the fastest-growing AI natives and...

How often does The Crew Podcast release new episodes?

The Crew Podcast has 49 episodes. Check the episode list to see recent publication dates and frequency.

Where can I listen to The Crew Podcast?

You can listen to The Crew Podcast on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.

Who hosts The Crew Podcast?

The Crew Podcast is created and hosted by Crew.
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