New type of content pillar for the Crew podcast / our media brand: live podcasts at our events.
This one was taken from our NYC padel event on August 28th at Reserve Hudson Yards. Can see a highlight video from the event here.
We thought we’d get some of the Crew team together to jam on all things GTM: Chris Balestras (co-founder of Crew), Cailen Dsa (co-founder of Crew), Curt Clauss (partner, heads up AE recruiting), Matt Roberts (partner; heads up BDR/SDR searches for us).
We jammed out on the new GTM re-brand, the new CRO hires @ some of the labs, our thoughts on how to choose the right company, why padel is so hot right now, and all things GTM/startups/AI.
We’ll start to test out some of these new formats, let me know what you think!
Some of our previous guests:
Eleanor Dorfman, Head of Commercial Sales @ Anthropic
Pat Forquer, CRO @ Legora
Graham Moreno, VP of GTM @ Parallel
Tomer Chernia, VP of GTM @ Cursor
Liam Mulcahy, Head of Sales @ Parallel (former GTM Operating Partner @ Kleiner Perkins)
Becca Lindquist, Head of Sales @ Clay
Nick Bogaty, CRO @ Vercel
Kyle Parrish, former VP of Sales @ Figma
Ghazi Masood, CRO @ Replit
Evan Cassidy, VP of Sales @ Decagon
James White, VP of Sales @ Rogo
Mark Ebert, SVP of Revenue @ Profound
Rob Saliterman, VP of Sales @ Harvey
Bardia Shahali, VP of Sales @ Granola
And many more in the pipeline - if you know any good leaders who fit this, shoot me a DM/reply/email ( [email protected] ). We’ll keep openings rolling and be super open to suggestions for similar guests.
We film in-person in SF & NYC at legit podcast studios and have retained a stellar post-production agency, so the quality will be high.
behind the scenes filming our episode with Graham Moreno, VP of GTM @ Parallel, back in May 2026
Links To Sections
Discussed In This Episode
Why Paul Graham thinks "GTM" sounds bogus, and why Crew is doubling down with 200 hats
The Stripe origin story of the GTM rebrand, and why every AI native inherited it
CRO musical chairs at the labs: Paul Smith, Denise Dresser, and Dolly's arrival
How Wiz ran the equivalent of a six-to-twelve-month enterprise sale in six days
Curt's 80/20 for vetting a startup AE role: tier one investor, inbound mix, real product market fit
Read the wins channel. Cobwebs and crickets tell you what the pitch won't
Andy Kofoid's four-to-five-year rule, and why it lacks nuance for startup operators
The three reasons people actually stay: quota, learning, equity
Commission breath: are the best reps coin operated, or is it the story behind the answer?
Prep, don't creep. Green flag if you did the research, red flag if you're weird about it
GTM mafias: Stripe, MongoDB, Metronome, Slack, Segment, Listen Labs, Cursor
Interesting Takeaways
1. The GTM Re-brand Is Here To Stay
Paul Graham kicked the hornet's nest asking why everyone suddenly calls themselves GTM. Chris's counter: words matter.
Everybody hates mayo, but tell him he's getting aioli with his fries at a nice restaurant and he's in.
Matt admitted he disagreed at first, since an SDR, a VP of Sales, a rev ops lead, and a field marketer can all say "GTM" and a recruiter can't tell who does what. Cailen's take: we started calling statisticians data scientists and nobody blinked.
The scope really did change. Early-stage sellers now run their own funnel, own post-sale, and sometimes vibe code the integration when there's no FDE around. Curt added the sharpest proof point: SEs, PMs, and founders with under two years of selling are getting real enterprise AE looks, and often outperforming career enterprise reps.
2. The Labs Are Changing How They Hire
Anthropic and OpenAI grew so fast they compressed a decade of team-building into a couple of years:
Stripe and Plaid people early, then Salesforce leadership eight months later. Now OpenAI is shifting again, with Denise Dresser out and Dolly (AppD, Wiz) in, a move toward the John McMahon / MongoDB lineage of reps who can create their own pipeline.
Curt's point on why it should work: Wiz's real edge wasn't old-school process, it was speed. They'd run the equivalent of a six-to-12-month enterprise sale in six days. As the number two player in enterprise, OpenAI needs that punch.
3. "Coin-Operated" Is About The Why, Not The Money
Chris's stance: the best reps aren't coin-operated.
Win and solve problems, and the money is the output. Curt reframed it: the best reps aren't short-term coin-operated. They're optimizing W2 over several years and actually vesting the equity, not maxing out this year.
Matt said it lives or dies on the story. "I want Wolf of Wall Street money" is a pass, "I want to retire my parents and pay off their mortgage" is an instant yes. Cailen drew the stage line: late-stage strat AEs can be pure hunters, but at Series A to D you need a builder who thinks like a shareholder. At Dropbox, they were allergic to candidates who called themselves coin-operated.
4. Want To Know If A Startup Is Ripping? Ask To See The Wins Channel
Curt's 80/20 for diligencing an AE role: tier one investor, mostly inbound, real product-market fit. Then go one level deeper and ask what the deal mix looked like over the last quarter or two.
Were deals 5K or 500K, and did multiple reps close them or was it all founder-led? Chris's sneaky version: ask to see the Slack wins channel. He's joined companies where it was cobwebs and crickets, and he probably wouldn't have signed if he'd seen it first.
5. Four To Five Years Is A Big-Company Take
Andy Kofoid (President @ Databricks) posted that it's a red flag if candidates haven't stayed four to five years at their companies. Chris thinks that lacks nuance for startup operators, where two to three years is the real anchor.
Cailen laid out why people actually stay: they're hitting quota and making money, they're learning from people they like, and the equity is still growing. Break one of those and they leave, usually because of a manager. He also pushed back the other way: nine years at one logo gets flagged as a red flag too, which he calls BS.
The line everyone agreed on: if you've had back-to-back-to-back short stints, it's probably you. Curt's version is to give people a mulligan, and a company mulligan too.
Key Timestamps
(00:00) Live from Hudson Yards: Crew's first live podcast
(05:00) Paul Graham vs. the GTM rebrand
(11:00) CRO musical chairs at OpenAI and Anthropic
(15:00) How Wiz ran a six-day enterprise deal
(20:00) Mark Ebert on Profound's pivot to multi-product
(29:00) The 80/20 of picking a startup AE role
(31:30) Read the wins channel before you sign
(39:00) Andy Kofoid's four-year rule, and why Chris disagrees
(45:30) Are the best reps coin-operated?
(55:30) GTM mafias: Stripe, Mongo, Metronome, Cursor
Thanks for tuning in!
If you enjoy it, please give us a rating, review, or follow on Spotify/YouTube/Apple Podcasts - it really helps us grow this.
For those who are new, my name is Chris Balestras, co-founder & head of talent, media, & brand @ Crew - a GTM recruiting, media, and investing firm, working with seed through series D AI-natives to help them grow.
Where to find Crew:
We work with many of the hottest AI-native startups in various capacities, and for those who are interested, shoot me an email at ( [email protected] ) or a DM on LinkedIn.
🫡 cheers,
Chris