The Crew Podcast

Crew

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. 4d ago

    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/

  2. 6d ago

    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/

  3. 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/

  4. Sep 18

    Building GTM Agents Live + The AI-Pilled AE Operating System w/ Nic Siegle, Founding AE @ Dust

    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 briefing delivered as a podcast, an Eisenhower matrix of AI recommended actions, live account plans with org charts, and a fresh AI generated seagull every day because life is short. Timestamps(00:00) The wrong thing at amazing scale (01:30) Welcome to the Crew podcast (02:31) Why Crew wanted to try a live demo episode (03:56) Nic's background, and what Dust actually is (06:11) The three stages of AI adoption inside companies (07:39) Open source Chinese models, and sitting on top of every model (08:30) The MCP timeline, and when tools started talking to each other (11:25) Was Opus the chasm? (12:54) The core sales use cases, from ask-sales bots to RFPs (17:10) Why "how AI pilled are you" is now an interview question (18:06) How Clay and 1Password govern who builds what (20:51) "Show me something you've built" (22:04) Building a pre-call prep agent from scratch (24:48) Picking a model, and the test that cost 178 times more (31:07) Idiot in motion versus the blast radius of AI (39:03) Setting a 7am trigger and emailing yourself the brief (44:48) Publishing an agent so the whole team can use it (49:26) Nic's cockpit: Pods and an AE operating system (55:36) Building an account plan with org chart and live product usage (01:01:15) Where to try Dust 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 ByDust: The platform for teams of humans and teams of agents to work together. Build agents without writing a line of code, connect them to your company's data and tools, and run them from Slack, a spreadsheet, the Chrome extension, or your phone. Dust sits on top of frontier and open source models so you can pick the right one for each job, with permissions, governance, and human-in-the-loop controls set per action. Trusted by Datadog, 1Password, and Clay. Try it at https://dust.tt/ 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. Sep 15

    The 0 to $20M GTM Traps + How To Diligence A Founder w/ Dini Mehta, Operating Partner @ Peak XV

    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 who fell into sales and then into tech, she spent roughly a decade selling top-down enterprise before deliberately taking a job in a category she knew nothing about. Timestamps: • (00:00) The AI theater • (01:41) Welcome to the Crew podcast • (02:39) Leaving the operator seat for Peak XV • (07:44) What Peak XV is, and her three engagement models • (10:25) The question she gets most in office hours • (11:23) Comcast, Drawbridge, and Lattice from $3M to $100M • (14:17) Two types of go-to-market leaders • (14:38) Top down versus bottom up, and where each one breaks • (18:06) Trap one: hiring AEs before you have demand • (20:27) Trap two: not hiring fast enough at 500% attainment • (22:14) Why she ignores resumes and logos • (24:31) Trap three: the founder who passes the hot potato • (26:27) Centralized or decentralized AI ownership • (29:05) Behind closed doors, none of it is solved • (31:20) How she diligences a company • (34:19) The hypotheticals that expose a founder • (38:08) Why traction alone has eroded as a signal • (38:47) The full body yes • (39:47) Run your own race • (42:22) What she would tell her younger self 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 CrewLinkedIn: https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Website: https://www.withcrew.ai/ Blog: https://www.withcrew.blog/

  6. Sep 8

    Why I Left VC To Get Back Into The GTM Operating Seat w/ Liam Mulcahy, Head of GTM @ Parallel

    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 agentic-native companies. He also makes the case that a modern GTM org needs 50% fewer salespeople up to half a billion in revenue, walks through the payback-of-one standard he holds new reps to inside 45 days, and explains what happens when a rep shows up with a PhD-level brief built in Claude and can't say whether the prospect is based in New York or San Francisco. It's his second time on the show, and he spends most of it arguing against the way sales teams are still being built. Discussed In This Episode • Why the innovator's dilemma gap has almost disappeared for companies building on the frontier • The 10 Fortune 500 deals Parallel closed in four months, and the bank that called it their fastest AI deal ever • Payback of one: covering a rep's full base salary in closed deals within 45 days • Why he thinks you need 50% fewer salespeople up until half a billion in revenue • Teaching classically trained sellers to be technical, and technical sellers to run a real process • The Claude brief that looks perfect and still can't tell you how the company makes money • Why "that ignorance is unemployment" if you're not building with these tools for fun • Leaving seven years in VC for an operating role, and the seven people who came with him • Why he wanted founders with perspective, and the Father's Day tea he didn't want to explain to a 24-year-old Timestamps: (0:00) Cold open + intro (3:00) The Paul Graham "GTM is bogus" tweet (4:12) From Kleiner Perkins back to the operator seat (9:57) Getting the band back together: the seven who came over (12:10) Picking your spot in the AI stack (16:02) The eval harness: a fourth party in every deal (23:36) Influencing deals you're boxed out of (27:43) The enterprise lag is dead (33:12) Capacity math: the Degnan debate & payback of one (39:35) Jevons paradox & the one-person-company myth (42:01) When to use AI in sales - and when it backfires (44:26) "How does this company make money?": the Claude doc story (50:51) The new org chart: deployed engineers & the end of the CSM (54:36) Paid extroverts: why founders hire consultants post-sale (56:37) Why Parallel will never hire BDRs (1:01:50) Ignorance is unemployment: every rep needs a GitHub (1:06:45) Where the talent went - and the Shawshank close 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 (a recruiting, investing, & media firm for seed through Series D AI-natives & fast-growing SaaS startups) sits down with GTM 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. About Crew Crew is a recruiting, investing, & media firm for seed through Series D AI-natives & fast-growing SaaS startups. Where to Find CrewLinkedIn: https://www.linkedin.com/company/crewgtmYouTube: https://www.youtube.com/@thecrewgtmNewsletter: https://www.withcrew.blog/Website: https://www.withcrew.ai/

  7. Sep 1

    Why Utah Produces Elite Sales Talent + Building The GTM Machine @ Exa w/ Marcus Holm, CRO @ Exa

    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, Dallas, Singapore, and the Bay Area. He started out knocking doors on commission in college, and before that spent two years in Latvia and Estonia selling religion to atheists in Russian, a language he did not speak when he arrived. Discussed in This Episode: • Why AI companies keep building their sales teams out of Utah, and what an 18-month church mission does to a person's tolerance for rejection • Why door-to-door is the most intimidating sale there is, and how telesales and field sales each get easier from there • Commission-only math: 25 reps go out for the summer, ten are left by the end of it • The 75% pay cut he took on purpose to leave door-to-door for an SDR seat at Cisco • Two special needs brothers, a sister who died of cancer, a father who went bankrupt, and the risk tolerance that came out of it • "Who will Claude not kill": the durability test he ran on Exa, and why years of sweat equity is the only real moat • Why Exa's human users are now growing faster than its agent users, which was not the founding thesis • The ICE framework, and why he will hire someone with no dev tools experience if the raw materials are there • The management belief he abandoned: that good sellers have to be wired like him • How LaunchDarkly went from 18% to 54% of reps over plan, and why "70 at 70" no longer holds in AI • Quota attainment benchmarks now: 30 to 40% is the norm, over 50% is best in class Timestamps: • (02:18) Welcome, and why Exa's investors kept texting Chris about Marcus • (03:30) Why AI companies keep building sales teams in Utah • (05:33) Why door-to-door is the most intimidating sale there is • (06:31) His father the sales trainer, Super Target, and the date that needed a car • (09:39) Commission only: 25 reps in June, ten by August • (12:38) The adversity that set his risk tolerance • (16:15) How he ended up a technical seller, and the superpower he found learning Russian • (19:09) Seattle, Heptio, and the orchestration wars • (21:34) Learn, earn, grow: how to pick your next company • (24:56) Channeling his inner VC on Exa • (28:27) Who Claude won't kill, and why the open source graveyard is the analog • (34:54) Websites vs. the API, and humans becoming the customer • (40:15) Signals, propensity data, and giving developers free consulting • (43:56) The ICE framework for hiring • (46:11) What he changed his mind about in hiring • (48:17) The AI tools his reps actually use • (51:55) From 18% to 54% quota attainment • (58:38) Forward deployed engineers and doing more with fewer people • (1:02:04) GTM mafias, and why the AI era is too early to call 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 an advisory, recruiting, investing, & media firm for seed through series C 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. Aug 25

    Why Remote Breaks at Scale & the GTM Playbook Behind AI Agents w/ Darren Moffett, VP of Sales @ LangChain

    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 orgs at three different companies, Darren also breaks down what separates a technical seller from someone who can just talk the talk, why remote work erodes at scale, and the "SDLC for agents" framework LangChain uses to sell a category of software that barely existed two years ago. It's the version of a first-year retro founders usually only tell in private. Discussed In This Episode - The MuleSoft hiring philosophy: "you control who comes in the front door," and the four criteria every candidate was screened against - Why the best litmus test for a technical seller isn't a resume line, it's whether they can demo their own current product under pressure - The comp plan mistake that had reps steering customers toward the wrong deployment model to hit quota - Why remote-first breaks down hardest for early-career reps, and where it still works fine - LangChain's "SDLC for agents": build, test, deploy, manage, and why agents can't be tested the way traditional software can - The three things he actually evaluates before joining a company, and why "the people" mattered more than the business model this time - Why he thinks pure consumption-based pricing is coming, and why LangChain isn't rushing there yet 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 (an advisory, recruiting, investing, & media firm for seed through series C AI-natives) sits down with GTM 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. About CrewCrew is an advisory, 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 Newsletter: https://www.withcrew.blog/ Website: https://www.withcrew.ai/

Ratings & Reviews

5
out of 5
9 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/

You Might Also Like