The Crew Podcast

Crew
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  • Technology
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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 breakouts. Find us @ https://www.withcrew.ai/ & https://www.withcrew.blog/

  1. 1d ago

    How to Build a Sales Team With No Sales Engineers w/ Steven Boone, VP of Enterprise GTM @ Perplexity

    Steven Boone is VP of Enterprise at Perplexity, where he joined about five months ago and now runs sales, customer success, consumer and enterprise support, forward deployed engineering, and rev ops. He got there without ever carrying a bag. After starting out in law school, he moved through product marketing and rev ops, served as chief of staff to the CRO at Twilio, and ran go-to-market at a seed-stage legal tech startup before leading enterprise sales at Zuora, a deliberate jump from Twilio's product-led motion into top-down deals. Since he arrived at Perplexity, every rep he has hired has closed a deal in their first 30 days. Timestamps: • (00:00) Clarity of thought over everything • (01:38) Welcome to the Crew podcast • (03:12) A nontraditional path to the revenue seat • (06:10) Turning support tickets into sales opportunities • (09:51) What Perplexity sells, from search API to Computer • (17:58) Leaving product-led Twilio for top-down Zuora • (20:08) Leading enterprise reps without carrying a bag • (22:25) Productize it or white glove it • (26:09) Complexity versus margin-adjusted ACV • (28:13) Kill the first discovery call • (31:44) Torn apart by AI • (36:12) Why Perplexity has no sales engineers • (42:36) How he interviews for clarity of thought • (46:54) Green, yellow, red capacity planning • (52:03) Why he said yes to sales About The Crew PodcastThe Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Crew, talks to the people actually building go-to-market motions in real time, not in retrospect. About CrewCrew is a recruiting, investing, & media firm for seed through series D AI-natives & fast-growing SaaS startups. This Episode Is Brought To You ByAttention: Put a team of revenue agents on every deal. Attention captures every customer interaction without a bot in the room, updates your CRM, automates your reporting, scores reps and opportunities against any framework, and forecasts in a way you can actually trust. Trusted by Lovable, Abridge, Avoca, and hundreds of other fast-growing companies. Try it at https://www.attention.com/ Metaview: The agentic recruiting platform, built for hiring end to end. Metaview's agents source and reach out to candidates in your own tone, review every inbound application against your criteria and tell you exactly why someone made the shortlist, join every call and deliver structured notes the moment it ends, and surface trends across your pipeline from salary expectations to AI fluency. Recruiters, hiring managers and agents all work off one layer of context, with permissions and a full audit trail behind every output. Trusted by Deel, Brex, Deliveroo, Replit and thousands of other teams. Start for free at https://www.metaview.ai/ Where to Find Crew LinkedIn: https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Website: https://www.withcrew.ai/ Blog: https://www.withcrew.blog/

  2. Oct 22

    This Week in GTM w/ Glenn Rachlin (OpenRouter) | Factory vs Cognition, AI GTM Talent Density, & More

    Glenn is the Head of Strategic GTM at OpenRouter, an AI infrastructure platform that helps businesses access and route requests across AI models, optimizing for factors like cost and performance. After building his career in crypto, including his time at Alchemy, Glenn has shifted his focus to AI, which he considers the most important technology in history. Now at OpenRouter, he operates at the intersection of AI infrastructure, enterprise sales, and the rapidly evolving ecosystem of AI-native companies. A student of go-to-market strategy and sales culture, Glenn has a front-row seat to the people, companies, and ideas shaping the next generation of tech. From the rise of AI-native sales teams and the talent wars unfolding across the industry to the unfiltered world of GTM Twitter, he brings a perspective shaped by years in crypto and a new chapter in AI. Discussed in This Episode: The Factory vs. Cognition controversyWhy GTM Twitter is where the conversation happensAI memes and the “butthole era” of logosHow to identify top GTM talent in AIWhat makes a sales team AI-nativeWhy being an order taker can be better than being a hunterWhy hunter AEs should earn moreGlenn’s shift from crypto to AIWhat OpenRouter does and how it worksHow AI agents are changing everyday work Timestamps: (00:00) Episode Preview (01:33) Welcome to the Crew Podcast (05:15) Factory vs. Cognition (13:04) GTM Twitter and AI Memes (20:18) AI Agents in Everyday Work (27:48) AI Talent and GTM Teams (31:30) Why AI Matters (33:00) GTM Culture and Memes (39:33) Why Order Taking Is the Best (44:05) The Hunter AE Debate (47:26) From Crypto to AI (50:22) Closing Remarks About The Crew Podcast The Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Crew, talks to the people actually building go-to-market motions in real time, not in retrospect. About Crew Crew is a recruiting, investing, & media firm for seed through series D AI-natives & fast-growing SaaS startups. Where to Find Crew LinkedIn: https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Website: https://www.withcrew.ai/ Blog: https://www.withcrew.blog/

  3. Oct 20

    From Yale Engineer to 3 IPOs: How to Hire the Right Rep for Your Sale | Rich Liu, ex-Navan CRO

    Most companies hire sales reps from the hottest logos and hope they work out. Rich Liu has built sales teams at Meta, MuleSoft and Navan, and his rule is to hire for the sale you're actually running. In this episode he breaks down how MuleSoft turned hiring into religion, why a great rep can fail in the wrong motion, and how Navan rebuilt its go-to-market when COVID took travel revenue to almost nothing. Rich's Background Rich Liu is a go-to-market advisor to AI-native companies and the former CRO at Navan (formerly TripActions), where he helped rebuild the business through COVID and on to an IPO. Before Navan he ran enterprise sales at MuleSoft, leading a team of a couple hundred people across six offices as the company went from roughly $800M in valuation to a 10x in three years. He joined Meta when it had around 2,000 employees and ran sales and account management teams as it scaled to 20,000. A Yale engineer by training, he got his start in a sales boiler room cold-calling for Fisher Investments after 9/11. Timestamps • (00:00) Cold open • (01:19) Welcome to the Crew podcast • (03:12) From Yale engineer to a sales boiler room • (05:47) Breaking into Meta • (08:24) Leaving Meta for a company named after a farm animal • (12:15) The MuleSoft pivot • (16:49) When hiring became religion • (22:38) Why you can't raise the bar later • (25:19) Know the sale before you interview • (27:45) The Vans store BDR • (37:39) Selling travel during a pandemic • (43:58) Advising AI-native companies • (45:57) Chasing Anthropic-level growth • (49:45) Which sales orgs produce the best reps About The Crew PodcastThe Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Crew, talks to the people actually building go-to-market motions in real time, not in retrospect. About CrewCrew is a recruiting, investing, & media firm for seed through series D AI-natives & fast-growing SaaS startups. This Episode Is Brought To You ByAttention: Put a team of revenue agents on every deal. Attention captures every customer interaction without a bot in the room, updates your CRM, automates your reporting, scores reps and opportunities against any framework, and forecasts in a way you can actually trust. Trusted by Lovable, Abridge, Avoca, and hundreds of other fast-growing companies. Try it at https://www.attention.com/ Metaview: The agentic recruiting platform, built for hiring end to end. Metaview's agents source and reach out to candidates in your own tone, review every inbound application against your criteria and tell you exactly why someone made the shortlist, join every call and deliver structured notes the moment it ends, and surface trends across your pipeline from salary expectations to AI fluency. Recruiters, hiring managers and agents all work off one layer of context, with permissions and a full audit trail behind every output. Trusted by Deel, Brex, Deliveroo, Replit and thousands of other teams. Start for free at https://www.metaview.ai/ Where to Find Crew LinkedIn: https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Website: https://www.withcrew.ai/ Blog: https://www.withcrew.blog/

  4. Oct 13

    Why Most AI Startups Aren't Defensible & Why 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 has worked with 100 to 150 companies across SaaS and AI, including Higgsfield AI. He started his career in recruiting and got out after a mentor told him that if you stay in recruiting long enough, you're a recruiter. Today he spends his time as a sounding board for founders and CEOs making the hires that shape their go-to-market. Timestamps • (00:00) Intro • (01:00) Welcome to the Crew podcast • (02:22) From LinkedIn to EchoSign to Gong • (06:42) Why hiring more AEs won't fix demand • (08:34) How the best companies create demand • (10:22) Advisory boards and warm intros • (16:34) Why resumes don't tell the whole story • (20:16) When to run a live role play • (22:46) Salespeople are pathological liars • (25:56) How to pick the right company to join • (28:20) Why 95 out of 100 startups won't make it • (30:59) The problem with secondaries: Ramp vs. Brex • (37:31) CPQ and contracts in a usage-based world • (40:21) AI can't fix product market fit • (42:50) The game film idea for hiring sales • (49:41) The sales mafias he respects • (53:49) Radical meritocracy and promoting from within • (01:00:00) The bootstrapped company that surprised him About The Crew Podcast The Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Crew, talks to the people actually building go-to-market motions in real time, not in retrospect. About Crew Crew is a recruiting, investing, & media firm for seed through series D AI-natives & fast-growing SaaS startups. This Episode Is Brought To You By Attention: Put a team of revenue agents on every deal. Attention captures every customer interaction without a bot in the room, updates your CRM, automates your reporting, scores reps and opportunities against any framework, and forecasts in a way you can actually trust. Trusted by Lovable, Abridge, Avoca, and hundreds of other fast-growing companies. Try it at https://www.attention.com/ Metaview: The agentic recruiting platform, built for hiring end to end. Metaview's agents source and reach out to candidates in your own tone, review every inbound application against your criteria and tell you exactly why someone made the shortlist, join every call and deliver structured notes the moment it ends, and surface trends across your pipeline from salary expectations to AI fluency. Recruiters, hiring managers and agents all work off one layer of context, with permissions and a full audit trail behind every output. Trusted by Deel, Brex, Deliveroo, Replit and thousands of other teams. Start for free at https://www.metaview.ai/ Where to Find Crew LinkedIn: https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Website: https://www.withcrew.ai/ Blog: https://www.withcrew.blog/

  5. Oct 6

    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 spent nearly a decade at Cloudflare, where he was the first outside sales leader hired, helped build its first sales teams, led the push into enterprise, and then built out the global go-to-market for its Zero Trust product. Earlier in his career he built new hire enablement at govtech company Granicus. He grew up in Port Washington, Long Island, and is now based on the West Coast. Timestamps: • (00:00) Welcome to the Crew podcast • (03:22) Why CVEs spiked almost 10x • (06:38) Pixel-perfect impersonations at machine speed • (07:58) Tying your deal to a corporate initiative • (10:36) Why security sells through the channel • (15:33) Selling middle out • (16:59) The champion in the corner of the room • (19:30) Creating urgency without ambulance chasing • (22:45) What's working in outbound • (25:07) Lessons from a decade at Cloudflare • (27:51) Why he always took the harder path • (31:44) Leaving Cloudflare for Outtake • (35:17) Hiring red flags and the AI question • (40:52) How the sales team uses AI agents • (42:21) Blocking AI for new hires in month one • (45:07) Enablement that starts with the Magna Carta • (49:14) Budget cycles and convening power • (53:59) Why he admires the number two players • (57:03) Inside the Outtake sales culture About The Crew Podcast The Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies.Every week, host Chris Balestras, partner @ Crew, talks to the people actually building go-to-market motions in real time, not in retrospect. About Crew Crew is a recruiting, investing, & media firm for seed through series D AI-natives & fast-growing SaaS startups. This Episode Is Brought To You By Attention: Put a team of revenue agents on every deal. Attention captures every customer interaction without a bot in the room, updates your CRM, automates your reporting, scores reps and opportunities against any framework, and forecasts in a way you can actually trust. Trusted by Lovable, Abridge, Avoca, and hundreds of other fast-growing companies. Try it at https://www.attention.com/ Metaview: The agentic recruiting platform, built for hiring end to end. Metaview's agents source and reach out to candidates in your own tone, review every inbound application against your criteria and tell you exactly why someone made the shortlist, join every call and deliver structured notes the moment it ends, and surface trends across your pipeline from salary expectations to AI fluency. Recruiters, hiring managers and agents all work off one layer of context, with permissions and a full audit trail behind every output. Trusted by Deel, Brex, Deliveroo, Replit and thousands of other teams. Start for free at https://www.metaview.ai/ Where to Find Crew LinkedIn: https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Website: https://www.withcrew.ai/ Blog: https://www.withcrew.blog/

  6. Oct 1

    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 Crew, heading up the AE and sales leadership practice. Twelve years in tech sales across Series A through E, including runs at Harvey and Outreach, plus founding AE experience. Matthew Roberts, Crew's SDR leadership practice, three months in. Ten years in SDR leadership, and hiring was always his favorite part. Caitlin Desai, Co-founder at Crew, running exec recruiting. Seventeen years as a GTM IC and leader at Bay Area companies including Box and Dropbox, and watched a company go from $1M to $1B in ARR. Plus drop-ins from Mark Ebert of Profound and George of Basis, Head of GTM. 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 - Mark Ebert on Profound's pivot from single-product to multi-product, and training a team running 150 miles an hour 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 About The Crew PodcastThe Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Crew, talks to the people actually building go-to-market motions in real time, not in retrospect. About CrewCrew is a recruiting, investing, & media firm for seed through series D AI-natives & fast-growing SaaS startups. Where to Find Crew LinkedIn: https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Website: https://www.withcrew.ai/ Blog: https://www.withcrew.blog/

  7. Sep 29

    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 four-month paper process feels broken to founders who watched the eval close in two days, and how each of them decides whether a candidate wants to learn the game or just extract from it. It closes somewhere more personal, on the conversations these guys had at home before taking the job. The Guests Liam Mulcahy is Head of Go-To-Market at Parallel. Jack Gashi is VP of Sales at Avoca Mark Ebert is SVP of Revenue at Profound Todd Busler is Head of Sales, Americas Discussed in This Episode: • Why annual territory and capacity planning falls apart when you hire this fast • Which things should stay written in pencil and which need to be written in pen • Deal caps and shutting off inbound to stop reps from sitting on pipeline • Why AE productivity benchmarks are made up right now, and everyone knows it • Jack on why equity is the wrong thing for most AEs to optimize for • The “worst 12 months” preview Clay gives candidates on purpose • Coin-operated vs. money-motivated, and how to tell them apart in an interview • The conversations these leaders had with their spouses before saying yes • Hiring people with young kids as a deliberate advantage Timestamps - (00:00) The worst 12 months of your life - (00:51) Welcome to the Crew podcast - (02:05) Headcount planning heading into next year - (02:50) Why most of the plan is written in pencil - (03:55) The four-month paper process nobody can explain - (11:53) When your best rep is also shipping code - (20:57) Moving the AM function into sales - (21:17) What you actually tell a candidate about quota and club - (24:47) Interviewing AMs and writing the rules as you go - (29:33) How do you do capacity planning right now - (29:55) Why the productivity math doesn't add up - (31:11) Reps turtling on deals - (32:33) Setting a deal cap ten minutes after the meeting - (34:14) It's a race, and what that does to coverage - (44:55) Forget the equity - (48:50) Coin-operated vs. money-motivated - (56:36) Hiring someone with a young kid at home - (61:09) Quality of time, and what the family actually sees - (75:04) The nuclear keys About The Crew Podcast The Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Crew, talks to the people actually building go-to-market motions in real time, not in retrospect. About Crew Crew is a recruiting, investing, & media firm for seed through series D AI-natives & fast-growing SaaS startups. Where to Find Crew LinkedIn: https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Website: https://www.withcrew.ai/Blog: https://www.withcrew.blog/

  8. Sep 22

    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 sales at Harvard Business School, a course that had 550 students last year and 70 sales coaches on staff, and he is the author of The Sales Acceleration Formula and The Science of Scaling. All proceeds from the new book go to mental health causes. Timestamps: • (00:00) Welcome to the Crew podcast • (00:58) The keynote that became the book • (02:06) The pattern behind the IPOs and the bankruptcies • (04:01) Hiring sales too early, and the VC treadmill • (05:52) Assessing the blitzscale risk of your category • (06:19) AI customer support versus software for airports • (07:02) Set a hiring pace, not a lump sum in January • (08:38) The dilution trap • (10:02) Twenty bets a decade versus your one • (12:24) Nobody agrees on what product market fit is • (13:26) Value creation, not revenue creation • (15:06) Slack's real North Star metric • (16:04) Go-to-market fit and unit economics • (17:16) The revenue velocity formula • (21:33) What is broken in venture capital • (26:12) How his Harvard sales class found product market fit • (29:39) Why he would hire MBAs right now • (30:41) Scorecard versus vibes • (33:42) The biggest hiring mistake founders make • (38:26) Hiring the startup person • (41:36) "I want them to cheat with AI" • (46:51) Selling time: 12 hours a week to 25 • (48:29) Paying HubSpot reps 25% more instead of hiring • (57:37) Why the book proceeds go to mental health About The Crew Podcast The Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Crew, talks to the people actually building go-to-market motions in real time, not in retrospect. About Crew Crew is a recruiting, investing, & media firm for seed through series D AI-natives & fast-growing SaaS startups. This Episode Is Brought To You By Attention: Put a team of revenue agents on every deal. Attention captures every customer interaction without a bot in the room, updates your CRM, automates your reporting, scores reps and opportunities against any framework, and forecasts in a way you can actually trust. Trusted by Lovable, Abridge, Avoca, and hundreds of other fast-growing companies. Try it at https://www.attention.com/ Metaview: The agentic recruiting platform, built for hiring end to end. Metaview's agents source and reach out to candidates in your own tone, review every inbound application against your criteria and tell you exactly why someone made the shortlist, join every call and deliver structured notes the moment it ends, and surface trends across your pipeline from salary expectations to AI fluency. Recruiters, hiring managers and agents all work off one layer of context, with permissions and a full audit trail behind every output. Trusted by Deel, Brex, Deliveroo, Replit and thousands of other teams. Start for free at https://www.metaview.ai/ Where to Find Crew LinkedIn: https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Website: https://www.withcrew.ai/ Blog: https://www.withcrew.blog/

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Ratings & Reviews

5
out of 5
10 Ratings

About

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 breakouts. Find us @ https://www.withcrew.ai/ & https://www.withcrew.blog/

Information

  • Creator
    Crew
  • Years Active
    2025 - 2026
  • Episodes
    52
  • Rating
    Explicit
  • Copyright
    © Crew
  • Show Website
    The Crew Podcast

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