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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

00:53:49

Cyber Risk Has Never Been Higher & Selling Cyber 101...

The Crew Podcast ·

2026/10/06

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 spent nearly a decade at Cloudflare, where he was the first outside sales leader hired, helped build its

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01:03:08

Live Podcast: The GTM Rebrand, CRO Musical Chairs &...

The Crew Podcast ·

2026/10/01

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 Crew, heading up the AE and sales leadership practice. Twelve years in tech sales across Series A

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01:31:14

GTM Roundtable: The State of AI-Native Sales w/ Clay,...

The Crew Podcast ·

2026/09/29

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 four-month paper process feels broken to founders who watched the eval close in two days, and how each of

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00:59:21

The Science of Sales + Why Founders Hire Sales Too...

The Crew Podcast ·

2026/09/22

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 sales at Harvard Business School, a course that had 550 students last year and 70 sales coaches on staff,

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01:02:25

Building GTM Agents Live + The AI-Pilled AE Operating...

The Crew Podcast ·

2026/09/18

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 better tool to play with, and he runs his own account executive operating system inside Dust: a morning

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00:43:10

The 0 to $20M GTM Traps + How To Diligence A Founder...

The Crew Podcast ·

2026/09/15

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 from pre-revenue to $140M ARR, and got her start in the early programmatic days at Comcast. An immigrant

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01:08:55

Why I Left VC To Get Back Into The GTM Operating Seat...

The Crew Podcast ·

2026/09/08

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 deal a major bank could remember, and those buyers are now evaluating with the same sophistication as

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01:03:03

Why Utah Produces Elite Sales Talent + Building The...

The Crew Podcast ·

2026/09/01

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 Beda, and at Cloudera during the Hadoop wars. He spent three and a half years at Cisco across Raleigh,

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00:56:36

Why Remote Breaks at Scale & the GTM Playbook Behind...

The Crew Podcast ·

2026/08/25

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 he had to abandon as the team scaled past 20 reps.As someone who's now built talent-dense sales

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01:02:03

Inside the GTM Playbooks at Twilio & Vanta w/ Stevie...

The Crew Podcast ·

2026/08/18

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 business: the world's first female pro gamer ("KillCreek"), then level design at Ion

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00:56:06

The First Sales Hire Mistake That Sinks Startups w/...

The Crew Podcast ·

2026/08/11

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 running strategic enterprise accounts, then joined Monte Carlo to learn a top-down, category-creation motion

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00:54:03

12 Things That Top Candidates Are Doing To Land...

The Crew Podcast ·

2026/08/06

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 reality check, this one pulls from both sides of the table: what Chris and Matt see every week placing reps

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00:48:49

How We're Scaling Vercel's GTM Motion Through A 9B...

The Crew Podcast ·

2026/08/04

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 by Cisco, where he helped scale the business from roughly $120M to $700M in ARR. It was at App

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01:01:19

How Clay Built the GTM Team Behind a $5B Valuation w/...

The Crew Podcast ·

2026/07/28

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 building the sales motion at Heap alongside Todd Baszler, going all the way back to 2017. A former D1

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00:52:36

Why Product Love Doesn't Actually Close Deals w/...

The Crew Podcast ·

2026/07/21

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, Entrepreneurship & Technology) put her in a room with brilliant early-stage technologists who had no

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00:58:22

Don't Take the Anthropic Job First w/ Mark...

The Crew Podcast ·

2026/07/14

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 at Ramp → now building GTM at Meadowview. Along the way, he brought in ~$100M in revenue for some of the

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00:52:36

How To Pick The Right AI Company To Bet On &...

The Crew Podcast ·

2026/07/07

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 data-center infrastructure, including a stint at Flexera, learning what large strategic

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00:26:44

State of GTM Recruiting @ The AI-Natives w/ Chris...

The Crew Podcast ·

2026/07/04

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-to-market recruiting for anyone trying to land at a Series A through D AI-native company in New York or

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00:58:11

Sales Mafias & What Made MongoDB Great w/ Graham...

The Crew Podcast ·

2026/06/30

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 building and leading enterprise sales, and came up through the legendary MongoDB sales org, the "Mongo

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01:01:47

How We're Building Granola Into the Most Beloved...

The Crew Podcast ·

2026/06/23

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 seed stage and helped take it from $0 to $20M ARR and a $1B valuation. In early 2024 he joined

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