The Crew Podcast
The Crew Podcast features interviews with go-to-market leaders and investors at fast-growing AI startups and early-stage companies. Each week, host Chris Balestras, co-founder of Crew — a GTM recruiting, media and investing firm focused on seed through Series D AI-native businesses — talks with operators about what is actually working in go-to-market today. The show focuses on practical, tactical insights rather than theory, drawn from people working directly in the field. Episodes explore how the next generation of AI-native and SaaS companies are building and scaling their sales and marketing efforts.
Episodes
Why AI Companies Aren’t Defensible & 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 through its acquisition by Adobe, and later at Talkdesk. He was involved with Gong from its inception and
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 impersonation and threats across the public internet, social media, and the dark web. Before Outtake, Steve s
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 PanelChris Balestras, Partner at Crew, hosting. Started at Salesforce, moved into early-stage sales, then founded Crew.Curt Clauss, Partner at
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 the first year is going to hurt.The conversation runs through deal caps and inbound throttling, why a fo
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, taking the company from zero to 100 million in revenue through its IPO. He teaches entrepreneurial sale
Building GTM Agents Live + The AI-Pilled AE Operating System w/ Nic Siegle, Founding AE @ Dust
Nic's BackgroundNic 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 usage data was the bread and butter. He describes himself as a tinkerer who cannot imagine a bet
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 over $100M ARR and from a single product to a platform. Before that she led go-to-market at Drawbridge fro
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 closed roughly 10 Fortune 500 enterprises in the last four months, one of them the fastest AI d
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%. Before that he led go-to-market at Heptio, the Kubernetes company founded by Craig McLuskie and Joe Be
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 worked until it didn't, the comp plan that had reps quietly gaming the system, and the hiring profile
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 Salesforce scale playbook that George Hu brought over. She got there on the least likely GTM resume in
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 leading sales teams in New York along the way. Post-acquisition, he did a stint inside Google Cloud runni
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 in 2026 from the ones who sabotage themselves before crossing the finish line.Part playbook, part reali
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 App Dynamics, first running post-sales, then stepping into the CRO seat after the company's acquisition
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 SDRs) and scaled it into one of the most respected go-to-market runs in data. Prior to that, she was bu
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 enterprise B2B SaaS. She got there by accident: a founder-track master's at Waterloo (Business, Ent
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 callbacks → founding enterprise hire at TripActions/Navan → two and a half years running enterprise
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 go-to-market motions in developer tooling. Earlier in his career he cut his teeth selling complex cloud and
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 happening on the front lines. Chris breaks them all down one by one.The result is a state-of-the-union on go-
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 President through the company's acquisition by Cognition. Earlier, he spent five years at Grafana Labs bui
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
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 re
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 R
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
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 adver
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
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 AB
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 P
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
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 BackgroundAdam 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,
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 entirely PLG and didn't even believe it needed a sales team. He helped build the outbound motion from t
How to Reinvent Yourself & The Athlete Mindset Behind Elite Sales Teams w/ Evan Cassidy @ Decagon
Evan Cassidy’s BackgroundEvan 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 the way from a team of ten through Series A, B, C, and D.Before Decagon, Evan held sales leadership roles
The $1M Salary GTM Role Nobody Qualifies For Yet w/ Jason Gelman, GTM Partner @ Primary VC
Jason Gelman’s BackgroundJason 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 & Operations at Compass, helping scale the company from ~$100M ARR to $6B through their IPO. He got his
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 just under four years, with 2025 growth outpacing 2024.Before Owner, Kyle spent three years at Shopif
My #1 Rep Closed $3.5M & Never Sold A Day In Their Life w/ Ghazi Masood, CRO @ Replit
Ghazi’s BackgroundGhazi 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 elite GTM teams in developer tooling.Before that, he spent 4+ years at Auth0, joining early and leading all
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 (where she turned multiple rejections into an eventual yes through sheer conviction and follow-through), m
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 wi
The Art & Science Of Choosing Which Startup To Join & How To Value Your Equity w/ Billy Gallagher, CEO @ Prospect
Billy’s BackgroundBilly 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 Rip
The Best Sales Reps Are Coin Operated & All Roads Lead Back To The Steak Dinner w/ Jack Gashi, VP of Sales @ Avoca
Jack's BackgroundJack 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
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 l
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
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
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
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
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 g
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) The YC Founder GTM Playbook: LinkedIn-First Outbound (20:00) Why LinkedIn Content Beats Cold Email (26:00)
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)(35:00) The AI Tools We're Actually Using Right Now(44:00) "Choose Company Over Title" - Is This Advice Actu
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 New Front Insurance, taking another company from seed to unicorn (with an IPO likely on the horizon). He st
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 the first 10 sellers at Square after working as a sales engineer at SAP, and spent time in venture capital
Recommended
Dark Night Tales with Brian King
Fantasy Flex
زن بودن
Medicine with Meaning
Yours Truly Johnny Dollar Collection
Take Back Your Health®
CBS Radio Mystery Theater | Old Time Radio
Solved Murders - True Crime Stories
紐約鳥｜New York Aperture
The Swerve Podcast: Obscure Topics | Conspiracy Theories
The Bread and Banter Podcast
The Church of What's Happening Now: The New Testament
