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PODCAST

The Crew Podcast

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

technology

All Episodes

00:56:10

How To Hire Sales Reps Like a Moneyball GM W/ Navid...

The Crew Podcast ·

2026/06/16

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 retail analytics startup and before that he co-founded a company focused on micro-location data and

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01:00:35

How The Best Salespeople Are Building Agents in GTM...

The Crew Podcast ·

2026/06/09

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 Recurrency, an ERP-adjacent platform selling into distributors and wholesalers. Before all of that, Roy

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00:57:24

Every Startup Is Lying to You, So Here's How to Pick...

The Crew Podcast ·

2026/06/02

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 during its era of dominance, where he experienced the wild "horse trading" culture of swapping accounts

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00:49:26

How Harvey Scaled GTM to an 11B Valuation w/ Rob...

The Crew Podcast ·

2026/05/26

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 advertising sales after a career in government, including time in the White House.Rob got into sales through

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00:51:16

Why The Best Sales Rep You Interview Is Probably Your...

The Crew Podcast ·

2026/05/19

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 early enterprise seller at Dropbox during the era when it was a "nearly impossible" sell,

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00:44:10

How We Built Profound’s GTM Motion To A $1B+...

The Crew Podcast ·

2026/05/12

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 ABM category leader. Before 6sense, Mark sold and led enterprise teams at Responsys / Oracle Marketing

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00:46:44

Why "AI for Finance" Is Meaningless & Why Bankers...

The Crew Podcast ·

2026/05/05

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 PerfectData (acquired by Nutanix pre-IPO), where he learned enterprise sales from a team of ex-Data

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00:55:49

The Old Sales Playbook Is Dead: Hiring + Selling In...

The Crew Podcast ·

2026/04/28

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 startups as an early go-to-market hire, then pivoted fully into AI about five years ago, before most

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00:57:48

Tell Them the Movie Before They Watch It: Enterprise...

The Crew Podcast ·

2026/04/21

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, joining when the company was at $20M ARR and helping scale to over $700M ARR. Before that, he got in

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00:51:46

Fewer Reps, More Pipeline: How AI-Native GTM Teams...

The Crew Podcast ·

2026/04/14

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 the ground up, moved into sales leadership, and scaled the company through hypergrowth to IPO.Prior to

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00:58:52

How to Reinvent Yourself & The Athlete Mindset Behind...

The Crew Podcast ·

2026/04/07

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 at Drift and Dropbox (after getting rejected the first time and doing a 10-month stint at Yelp to build

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01:04:02

The $1M Salary GTM Role Nobody Qualifies For Yet w/...

The Crew Podcast ·

2026/03/31

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 start in the New York tech scene after attending law school, where he quickly realized the meritocracy

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01:07:44

How The Best CROs Actually Hire Salespeople w/ Kyle...

The Crew Podcast ·

2026/03/24

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 Shopify where he built out the Point of Sale go-to-market organization and then ran the Canadian market, which

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00:49:15

My #1 Rep Closed $3.5M & Never Sold A Day In Their...

The Crew Podcast ·

2026/03/17

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 aspects of revenue growth for the Americas - scaling from $28M to $300M+ in 4 years before Okta

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00:56:43

Why Anthropic is The Hottest Company in AI & & How To...

The Crew Podcast ·

2026/03/10

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), moved to Segment, where she transitioned from customer success into sales and built the expansion motion,

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00:23:15

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

The Crew Podcast ·

2026/03/03

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

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00:55:14

The Art & Science Of Choosing Which Startup To Join &...

The Crew Podcast ·

2026/02/24

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 Rippling as the 34th employee in a generalist "special projects" role, staying for three and a

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01:05:28

The Best Sales Reps Are Coin Operated & All Roads...

The Crew Podcast ·

2026/02/17

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 build durable GTM teams. Prior to that, he worked in ad sales at Foursquare during the company’s peak

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01:06:13

The Words You Use Are Killing Your Trust & What Great...

The Crew Podcast ·

2026/02/10

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

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00:57:53

Why You Should Join Cursor Over OpenAI and Anthropic...

The Crew Podcast ·

2026/02/03

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

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