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The Crew Podcast

Crew
Go-To-Market
Artificial Intelligence
Tennr
Sales
Anthropic
ROX
Rogo
Unframe AI
Artificial Intelligence In Sales
Prospect
Braintrust
Clay
Harvey
Adam Ali
Decagon
Claude
Unifi
Avoca
Replit
Investment Banking

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... more

PublishesWeeklyEpisodes39Founded10 months ago
Number of ListenersCategory
Technology

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Artwork for The Crew Podcast

Latest Episodes

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 5... more

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 ... more

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... more

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... more

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Recent Guests

Rafa Jara-Simkin
Partner at Theory Ventures
Theory Ventures
Episode: The First Sales Hire Mistake That Sinks Startups w/ Rafa Jara-Simkin, Partner @ Theory Ventures
Matt Roberts
Crew's first hire; joined as part of Crew's initial team
Crew
Episode: 12 Things That Top Candidates Are Doing To Land Offers in 2026 w/ Chris Balestras, Co-founder @ Crew
Nick Bogaty
Chief Revenue Officer, Vercel
Vercel
Episode: How We're Scaling Vercel's GTM Motion Through A 9B Valuation w/ Nick Bogaty, CRO @ Vercel
Becca Lindquist
Head of Sales at Clay
Clay
Episode: How Clay Built the GTM Team Behind a $5B Valuation w/ Becca Lindquist, Head of Sales @ Clay
Simran Duggal
VP of Sales at Juicebox
Juicebox
Episode: Why Product Love Doesn't Actually Close Deals w/ Simran Duggal, VP of Sales @ Juicebox
Mark Goldberger
VP Sales at Metaview
Metaview
Episode: Don't Take the Anthropic Job First w/ Mark Goldberger, VP Sales @ Metaview
Bryan Cox
VP of Worldwide Sales at Braintrust
Braintrust
Episode: How To Pick The Right AI Company To Bet On & Operationalize Champion Building w/ Bryan Cox, VP of Worldwide Sales @ Braintrust
Graham Moreno
VP Go-To-Market at Parallel Web Systems
Parallel
Episode: Sales Mafias & What Made MongoDB Great w/ Graham Moreno, VP Worldwide GTM @ Parallel
Bardia Shahali
VP Sales at Granola
Granola
Episode: How We're Building Granola Into the Most Beloved Product in AI w/ Bardia Shahali, VP Sales @ Granola

Host

Chris Balestras
Host of The Crew Podcast (fka The Vibescaling Podcast); partner at Vibescaling; runs a GTM recruiting, media, and investing firm

Chart Rankings

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Apple Podcasts
#185
United States/Technology
Apple Podcasts
#159
Finland/Technology

Talking Points

Recent interactions between the hosts and their guests.

The Art & Science Of Choosing Which Startup To Join & How To Value Your Equity w/ Billy Gallagher, CEO @ Prospect
Q: How should I think through equity when evaluating multiple offers, and what are the 101s I should know?
The overview is that early-stage offers usually involve stock options with tax advantages and potential upside, while later-stage offers often use RSUs with simpler management but different liquidity dynamics. Key considerations include the total shares outstanding, fully diluted equity, and the dollar value at both preferred and fair market value; also important are QSBS eligibility, early exercise, and the post-termination exercise window, all of which can dramatically affect tax outcomes and flexibility.
How The Best CROs Actually Hire Salespeople w/ Kyle Norton, CRO @ Owner.com
Q: Give everybody a little bit of background on your trajectory in tech sales.
Kyle describes starting during the 2008 financial crisis, rising quickly into leadership, building GTM teams at Shopify and Owner, and scaling from a couple million ARR to close to $100M ARR, with a focus on disciplined hiring, enablement, and a data-driven, transparent leadership style.
How We're Building Granola Into the Most Beloved Product in AI w/ Bardia Shahali, VP Sales @ Granola
Q: How do you think about building the go-to-market engine and staffing in the AI era?
Start with a bottoms-up foundation, then layer in the right balance of AEs and technical or pre/post-sales support based on the ICP and the sales motion; avoid overbuilding technical roles where not needed and be transparent about current capabilities and process when hiring.
How We're Building Granola Into the Most Beloved Product in AI w/ Bardia Shahali, VP Sales @ Granola
Q: What advice would you give to somebody on how to choose the right company in AI, and inputs to consider?
Look for actual demand and a bottoms-up engine; be willing to take a junior role at a company that already has traction rather than chase a senior title at an undemonstrated company. Also assess founder-market fit and whether the company has a product you're excited to sell.
Why You Should Join Cursor Over OpenAI and Anthropic & How To Avoid Bad Sales Hires W/ Tomer Chernia, VP of GTM @ Cursor
Q: What makes Cursor a compelling place to work for top GTM talent with competing offers from Anthropic and OpenAI?
Cursor offers an opportunity to shape a fast-growing GTM motion at a company still small enough to leave a tangible imprint, with deep involvement across product, sales, and go-to-market, and a culture that rewards practical impact and ownership.

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Frequently Asked Questions About The Crew Podcast

What is The Crew Podcast about and what kind of topics does it cover?

The show spotlights GTM leaders and investors at AI-native startups and fast-growing SaaS companies, with weekly conversations that cut through hype to reveal practical, battle-tested strategies for selling AI products. Episodes routinely cover building and scaling GTM motion from the ground up, hiring the right leaders, enabling teams, and navigating enterprise buying with a focus on real-world results. A standout throughline is blending product-led and sales-led motions, embracing AI-assisted tooling, and prioritizing experimentation, rapid iteration, and storytelling that closes deals. The host's background with a go-to-market recruiting, media, and investing firm often surfaces candid anecdotes about team-building, culture, and the real... more

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1. The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
2. Revenue Builders
3. Grit
4. All-In with Chamath, Jason, Sacks & Friedberg
5. David Senra

How many episodes of The Crew Podcast are there?

The Crew Podcast launched 10 months ago and published 39 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on The Crew Podcast?

Recent guests on The Crew Podcast include:

1. Rafa Jara-Simkin
2. Matt Roberts
3. Nick Bogaty
4. Becca Lindquist
5. Simran Duggal
6. Mark Goldberger
7. Bryan Cox
8. Graham Moreno

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