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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/

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  • 30 episodes
  • weekly
  • Avg 56 min
  • English

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  • Tuesday · 53 min

    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/

  • October 1 · 1 hr 3 min

    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 Panel Chris 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 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/

  • September 29 · 1 hr 31 min

    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/

  • September 22 · 59 min

    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/

  • September 18 · 1 hr 2 min

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

    Nic's Background Nic 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 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 Dust: 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/

  • September 15 · 43 min

    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/

  • September 8 · 1 hr 8 min

    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/

  • September 1 · 1 hr 3 min

    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/

  • August 25 · 56 min

    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 Podcast The 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 Crew Crew 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/

  • August 18 · 1 hr 2 min

    Inside the GTM Playbooks at Twilio & Vanta w/ Stevie Case, CRO @ Vanta

    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 Storm, then mobile games in LA, until a vendor offered her a junior sales job and she took it because it scared her. She's also a partner at 20Sales, Harry Stebbings' GTM-operator sub-fund at 20VC. In this conversation, Stevie walks Chris through the two runs that defined her career and the frameworks she pulled out of them: why product-market fit is a feeling before it's a metric, the quota-to-OTE ratio she'd never hire below, and the one fundamental flaw she watched compound at Twilio that AI companies are repeating today, chasing growth while margins quietly rot underneath. Timestamps: (0:00) Cold open (4:01) What competitive gaming taught her about running a revenue org (5:04) The pivot from gaming to sales, and "why not me" (7:33) Why most people doing something great are doing it for the first time (8:39) Betting on grit over pedigree in hiring (9:13) How she actually assesses for curiosity in an interview (11:50) Product-market fit is "non-negotiable and visceral" (13:01) Defining PMF when the word feels fluffy (16:37) What a real PMF signal sounds like on a gong call (17:13) The pain question at the heart of discovery (18:54) The Salesforce playbook George Hu brought to Twilio (20:25) Sales as a science with art as the cherry on top (22:41) The one deep, fundamental flaw in the Twilio model (24:52) Margin vs. growth, and the questions to ask before you join (26:48) Why she left Twilio at its peak to join Vanta (29:54) How to test whether a founder is truly ready to scale (31:42) When the sales-led math actually makes sense (33:50) The quota-to-OTE ratio she'd never go below: 4 to 1 (35:15) Attainment benchmarks: 80% at 80%, 60% at 100% (38:50) Why pipeline doesn't just go up and to the right (39:02) The "Hunter AE" red flag, and what healthy outbound looks like (41:47) Moving Vanta upmarket into enterprise (45:35) Selling compliance vs. selling Twilio up market (47:35) Business case and ROI across segments (49:14) The modern sales team composition, and cold calling's comeback (50:07) Why the next generation of CROs won't be classic closers (52:25) The one skill VPs of sales are missing to make CRO (54:30) Building Vanta's own tools in-house with Claude Code (56:08) The GTM teams she admires (58:09) How she cut the filler words (59:09) Her advice for reps who want to break into VC 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 (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 Crew Crew 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/

  • August 11 · 56 min

    The First Sales Hire Mistake That Sinks Startups w/ Rafa Jara-Simkin, Partner @ Theory Ventures

    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 under Jordan and Barr. He later built an executive coaching practice before Tomasz pulled him into Theory, where he now advises portfolio founders on building their first sales teams. He's a Santa Cruz surfer, a recovering economist, and deeply interested in the inner game of leadership. Timestamps: • (09:23) Origin story: How Rafa fell into sales and snuck into Looker through the back door • (13:29) The Looker rocket ship: 25 to 1,000 employees, $1M to $100M+ ARR • (17:17) Where the Looker mafia went and what made those hires work • (19:09) Selling to developers vs. app-layer buyers: two different personas • (31:57) The mistakes founders keep making with their first sales hires • (35:43) Three types of founding sales roles (including the disaster zone) • (39:34) What's new in the portfolio: open source, inference costs, and margins • (41:45) Why enterprise buyers now diligence your token margins • (44:33) Theory's thesis and the app-layer "Goldilocks zone" vs. Anthropic • (48:52) Why generic sales advice is B.S. without context • (55:55) Executive coaching: what founders actually struggle with • (59:37) Rapid fire: AI tools, elite GTM teams, and creative outreach 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 C AI-natives & fast-growing SaaS startups. This episode is brought to you by the following sponsors: Parallel Parallel is where AI agents go to find answers. They've indexed the web from the ground up, built specifically so agents can pull accurate, low-latency, token-efficient web data. Parallel powers agents at the fastest-growing AI-native companies and the Fortune 500. And if you sell for a living, which most of you listening do, go-to-market engineers use Parallel to run real-time monitors on their accounts, catching funding rounds, exec changes, and product launches the moment they happen. They use it to automate account research and enrichment at scale. Get started today for free at parallel.ai Attention Sellers were hired to sell, not to fill in the CRM. Attention records and understands every sales call, then automatically updates your CRM, sends follow-ups, and scores reps against frameworks like MEDDIC, BANT, or your own custom methodology. Next best actions are proactively generated from there, and you get a clean pipeline, coaching on every call, and forecasting you can actually trust without asking reps for more admin. Turn your call recordings into a GTM operating layer with attention. Try them today at attention.com 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/

  • August 6 · 54 min

    12 Things That Top Candidates Are Doing To Land Offers in 2026 w/ Chris Balestras, Co-founder @ Crew

    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 and sellers at AI-native companies, and the small, high-leverage habits most candidates never think to run. As a co-founder of Crew and a former enterprise seller, Chris brings the company-side filter, while Matt brings a decade of BDR and SDR leadership and the candidate's-eye view of what actually moves a hiring manager. Timestamps (00:00) Cold Open: The Highest-Leverage Interview Habits, Previewed (01:31) Welcome + Why Chris Brought a Second Voice on a "Solo" Episode (02:22) The Premise: 12 Things Top Interviewers Do and Avoid to Land Offers in 2026 (04:06) Who Is Matt Roberts: Bartending in Santa Barbara to Crew's First Hire (09:54) #1 Respond Back Fast: Why Speed Is the Number One Tell (14:07) #2 Send the Thank-You: The Lost Art and How to Write One That Lands (16:23) #3 Bring the Right Energy: The Developer-Sales Advice That Backfired (21:21) #4 Show That You Want It: Telling a Company They're Your Number One (24:41) #5 "Tell Me About Yourself" in 90 Seconds or Less (28:00) #6 Be Structured: The Consulting Trick That Makes You Sound Sharper (30:07) #7 Stack the Cards in Your Favor: Make the Case Study Easy Mode (32:35) #8 Do the Job Before You Have the Job: Prospect and Multi-Thread the Loop (36:54) #9 Optimize for Curiosity, Not for Proving You're Smart (42:14) #10 Negotiate, But Don't Over-Negotiate: How Offers Get Pulled at the Finish Line (47:20) #11 Don't Bash Companies: What It Signals About Your Resilience (49:33) #12 Use Multiple Offers as Leverage Without Playing Hard to Get (52:48) Wrap: Weekly Episodes, the GTM Tweet Format, and Pedal in SF + NYC 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 (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 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 Newsletter: https://www.vibescaling.blog/ Website: https://www.withcrew.ai/

  • August 4 · 48 min

    How We're Scaling Vercel's GTM Motion Through A 9B Valuation w/ Nick Bogaty, CRO @ Vercel

    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 Dynamics, that a self-described product guy (and history major) fell in love with the craft of sales. After a few CRO runs, he landed at Vercel six months ago to help answer the two questions he cares most about: how people will design, and how people will build, in the AI era. Discussed In This Episode The non-linear path from open-source product guy to enterprise CRO The App Dynamics SKO that made him fall in love with sales The "value pyramid": why great sellers talk about the customer's company, not their own How App Dynamics scaled from $120M to $700M ARR without the best product The operational cadence behind predictable pipeline (and why two customer meetings a day is the floor) "Show me the receipts" and how to test whether a candidate drove the growth or rode the wave The coachability red flag he watches for in the first interview Why he joined Vercel: how people will design and build in the AI era Signal-based GTM and turning plug motion and open-source momentum into enterprise deals Building Athena, Vercel's homegrown GTM engine Why the most creative way into a company is to build something and show it Timestamps (0:00) From product guy to CRO: Nick's non-linear path (4:31) The App Dynamics SKO that converted him to sales (6:53) The value pyramid: make it about their company, not yours (10:48) The operational cadence behind $120M → $700M ARR (12:16) Winning enterprise with the 4th-best product (14:24) "Do you have a mole in my company?" (17:20) The hardest part of sales: discipline (18:04) Why Nick joined Vercel: how we'll design and build next (21:03) Adobe's font team and why taste now wins (24:24) Collapsing GTM headcount with AI agents (26:50) Was it the rep, or the rocket ship? (29:30) "Show me the receipts" (33:42) Selling the mission to someone who isn't looking (35:32) The coachability test in every first interview (37:39) Weekend warriors and signal-based GTM (39:23) Turning ground-up momentum into enterprise deals (41:18) Usage vs. commitment in a consumption world (43:56) The sales team Nick admires most: Datadog (45:36) Building Athena: Vercel's homegrown GTM engine (47:45) The most creative way to get a sales team's attention 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 (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 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 Newsletter: https://www.withcrew.blog/ Website: https://www.withcrew.ai/

  • July 28 · 1 hr 1 min

    How Clay Built the GTM Team Behind a $5B Valuation w/ Becca Lindquist, Head of Sales @ Clay

    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 rower at Cal, she traces her competitive streak straight back to her time spent in that boat, and she's now building Clay's sales team from a group of artists and generalists toward hundreds of reps. Discussed in this episode: Why she optimizes for people over product or market, and the booze-cruise gut check that sealed the Clay decision The best way to use AI in GTM: Waste Management's green-dumpster play and the Tide sentiment workflow Building a pipe-gen muscle before the inbound music stops Why "how much pipeline do you self-source?" is a useless interview question The mock-call-plus-deal-debrief that replaced the memorized product demo Spike in product or spike in sales: how Clay hires when there's no playbook yet No variable comp, on purpose and the signal that it's time to switch it on The autopilot trap: how to tell you're decaying at a good company "Learn like Mongo, join like Stripe" and the two tracks for a sales career in AI The biggest mistakes founders make hiring their first sellers Timestamps: (0:00) Cold open (1:40) Welcome + why Becca chose Clay (2:30) The Brooklyn walks with Varun, and optimizing for people (6:27) "Are they your people?" and why you should always vet the team first (9:06) Joining at $100M (mostly PLG) vs. dbt at sub-$1M (11:06) Diligencing product love before joining (13:16) Pipe-gen culture: grow while the sun shines (14:08) The World Cup analogy: predict the future for the team (14:56) Hiring for outbound: the "favorite deal" question (17:23) The Spotify-playlist cold open, and spotting hunters (18:05) The healthy pipeline split, and Clay Day (19:52) SDR/AE pods, pipeline channels, and Tuesday readouts (23:53) The best way to leverage AI in GTM (28:20) Your alpha: executing on new ideas faster than competitors (31:43) The Waste Management green-dumpster play (33:08) Running a hiring seminar: how to read a LinkedIn profile (37:09) The 80/20 of a great mock call (38:01) Teaching vs. learning: the rhythm of the best calls (45:02) Comp in a usage-based, land-and-expand business (46:17) Company selection and the leap of faith (48:31) The autopilot trap: decay vs. loyalty (50:25) Sales orgs she admires: the MongoDB lineage (52:28) Learn like Mongo, join like Stripe (53:34) The biggest mistakes founders make hiring sellers (56:44) Reading energy: "what does your Friday look like?"(59:55) How to actually stand out to when applying to Clay 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 (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 Crew Crew 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/

  • July 21 · 52 min

    Why Product Love Doesn't Actually Close Deals w/ Simran Duggal, VP of Sales @ Juicebox

    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 idea how to commercialize, and she realized selling was the craft she wanted to build. In this conversation, she and Chris get into the learnings from scaling PLG into enterprise, the traits she screens for when hiring sellers in the AI era, and why the old sales playbooks no longer apply. Discussed in this episode: Why loving a product and buying it are two different things, and how a pipeline of fans inflates your forecast Selling to users vs. buyers, and to marketers vs. developers The number one trait she screens sellers for: mental resiliency Hiring "spikes" over generalists to raise the whole team's ceiling Scrapping the job title to hire in the AI-native era The mock discovery call and the feedback round that actually decides it Why personalization is about the buyer's problem, not their alma mater, and why the phone call still converts How the best talent leaders are becoming business strategists Why she believes the universal sales playbook is dead Timestamps: (0:00) Background: from Waterloo's founder track to sales (4:34) Founder mistakes: conviction pointed the wrong way (5:31) Webflow: joining as an early enterprise rep (6:22) Two-engine companies: why she wanted PLG + sales (7:27) The downside of selling on a PLG base (10:30) User vs. buyer: what Webflow got wrong (11:57) Marketers vs. developers: the art of vision casting (15:46) Webflow as a GTM talent factory (19:28) Hiring spikes: elevate everybody, raise the bar (20:58) The number one trait: mental resiliency (23:18) The mock discovery call (24:52) The feedback round that decides it (27:14) Reading a career: running toward vs. away (28:42) Leaving Webflow, betting on AI-native (33:06) Why recruiting: the Juicebox thesis on people (40:24) Talent leaders as business strategists (43:33) Outbound that works: pick up the phone (46:24) The AI tools she can't work without (50:05) The sales advice Simran thinks is dead (51:42) How to actually get Simran’s attention 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 C AI-natives & fast-growing SaaS startups. Where to Find Crew LinkedIn: linkedin.com/company/crewgtm YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg Newsletter: withcrew.blog Website: withcrew.ai This episode is brought to you by Dust. AI has made individual GTM work faster. But it hasn't made GTM teams more coordinated. Too much work still happens in silos. One person, one agent, one threat at a time. Dust gives teams of humans and agents a shared workspace to move complex go-to-market work forward using the right model for the job. Think account command centers, RFP deal rooms, and cross-functional launches. Instead of keeping AI work trapped in threads, Dust makes agents part of how your team coordinates makes decisions and drives work. That's multiplayer AI, and that's Dust. Check it out at: https://dust.tt/

  • July 14 · 58 min

    Don't Take the Anthropic Job First w/ Mark Goldberger, VP Sales @ Metaview

    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 most sought-after companies in tech. This one is for founders deciding when to invest in enterprise, VPs rethinking productivity metrics in the AI era, and reps with a weird résumé trying to break into a company that keeps ignoring their applications. Discussed in this episode: The 80/20 rule of sounding smart with a wine list (from a former somm who tasted 5,000 wines a year) Why breaking into SaaS with a non-traditional background is all about persistence, creativity, and finding an ally The 1% move: candidates who learn the product and demo it back to you Company selection as a concentrated VC bet: TAM, founders, and real customer love Why enterprise is a conviction test most companies fail at the 90-day mark The pricing tell: if you're only losing on price 10–15% of the time, you're too cheap Logos over margins early, and why ten enterprise logos beat the deal economics The MEDDPICC-as-activity method, and the rep who taught Claude to run it Why in-person sales came back, and why the human is the differentiator when everyone has AI The ten-second LinkedIn scan: trajectory, job-hopping, and builder DNA Breaking in when you don't fit the rubric — earn your way up the mountain "No champion, no deal" applies to hiring as much as selling Token-maxing vs doing more with less Timestamps: (00:00) Cold open: the concentrated bet of company selection (03:10) Long Island roots and the wine-sales origin story (05:19) From wine to SaaS: the impetus to switch (06:56) 100 applications, zero callbacks: breaking in without the résumé (08:15) The 1% move: candidates who demo your product back to you (09:30) Company selection as a concentrated VC bet (11:02) What TripActions and Ramp got right: talent density and PMF (14:49) The 180-degree flip: selling SMB vs. enterprise (18:25) The pricing tell: how much resistance is too much (19:10) AI fluency in the field: the rep who taught Claude MEDDPICC (22:26) Pilot data → insights → a Lovable dashboard built by an AE (25:36) The $10M-per-rep quota myth vs. product-market fit (33:39) The ten-second LinkedIn scan: green flags and red flags (37:29) Earn your way up the mountain: double-A before the home runs (39:08) Non-obvious beats obvious: selling travel during a pandemic (41:09) What changes when you're hiring a leader vs. an AE (46:47) No champion, no deal: hiring works like a sales process (49:04) The top GTM teams in the SaaS and AI era (51:07) Favorite quotes: pressure is a privilege, job's not finished (52:52) The art of taking away: brevity in the AI era (55:26) What Meadowview does: agentic recruiting, sourcing, and application review 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 (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 C AI-natives & fast-growing SaaS startups. Where to Find Crew LinkedIn: https://www.linkedin.com/company/crewgtm/YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_KhrlxgNewsletter: https://www.withcrew.blog/Website: https://www.withcrew.ai/

  • July 7 · 52 min

    How To Pick The Right AI Company To Bet On & Operationalize Champion Building w/ Bryan Cox, VP of Worldwide Sales @ Braintrust

    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 "whale-hunting" deals look like in action. A former college tennis player and self-described history major who fell into sales, Bryan treats the work like the craft it is, and is moving his family from Santa Barbara to the Bay Area to get closer to the action. Timestamps: (00:00) Cold open: the one-click "no" that exploded a seven-figure deal (01:22) Welcome to the Crew podcast + sponsors (02:52) From early cloud computing to Flexera's whale-hunting deals (06:02) Why Grafana produced so much elite sales talent (07:23) Choosing Braintrust: going where the highest-value problem is (09:34) Job as craft: loving the technical, hard-to-understand sale (13:31) What separates great reps from good ones on enablement (14:35) Sales as an ultramarathon: balance, burnout, and your "why" (22:05) The motion offense: circling a deal instead of running waterfall (25:08) The seven-figure deal that died, and operationalizing champions (29:41) How to interview a company: TAM, durability, and who's buying (33:10) The 40-call diligence process before joining Braintrust (36:50) Why everyone's moving to voice agents for ramp and enablement (42:25) The AI tool stack and a hot take on too much DIY (44:21) Rapid fire: GTM teams he admires and what he tests for in hiring (46:47) "Why are you in sales?" and the Shrek/onion test (50:44) The most creative way to break into Braintrust (hint: it’s not through Bryan) 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 C 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/ This episode is brought to you by the following sponsors: Dust AI has made individual GTM work faster. But it hasn't made GTM teams more coordinated. Too much work still happens in silos. One person, one agent, one threat at a time. Dust gives teams of humans and agents a shared workspace to move complex go-to-market work forward using the right model for the job. Think account command centers, RFP deal rooms, and cross-functional launches. Instead of keeping AI work trapped in threads, Dust makes agents part of how your team coordinates makes decisions and drives work. That's multiplayer AI, and that's Dust. Check it out at: https://dust.tt/ Centralize If you work complex enterprise deals, the hard part is an effort, it's visibility. Who we met with on this account? Who's gone quiet? Who's on my team who can open a door that we haven't knocked on yet? Centralize answers all three of those questions. It builds a live stakeholder map for every deal, pulling from Salesforce, email calls, and your team's networks and then telling you where to go next. Teams at LangChain, Decagon, Webflow, and Cognition run on it. Try it on a live deal now at usecentralize.com.

  • July 4 · 26 min

    State of GTM Recruiting @ The AI-Natives w/ Chris Balestras, Co-founder @ Crew

    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 SF right now. As a co-founder of Crew and a former enterprise seller for seven years, Chris works with nearly every company in the market, and he uses that vantage point to separate the takes he agrees with from the ones he thinks miss the mark. Discussed In This Episode Why the “never hire from Salesforce” take is half right and half wrong, and the three risk vectors Chris actually screens for The hidden difficulty of selling at a brand-name incumbent, and the real tell that should make you skeptical of a five-year Salesforce rep Why hiring out of security is its own puzzle, and the few orgs still running a hard, direct, technical sale The clean benchmark Chris is “stealing” for his advising: $1.5M of productivity per rep as the line between hiring faster and overhiring Why you should always set quotas slightly too low, and the morale death spiral when you set them too high Windfall clauses explained: why companies are capping payouts on $20–30M deals, and why it’s actually a good sign Why raising a huge round tells you almost nothing about whether it’s a good go-to-market opportunity The forward-deployed engineer debate, and why Chris disagrees that it’s just glorified professional services Why even great operators need an accountability partner, and the personal-trainer analogy for recruiters How Anthropic is pulling the best reps out of the market, the de-risking logic driving it, and why it looks like Salesforce in 2001 The Snowflake hiring mistake that may have let Databricks inflect past them Why so much VC go-to-market advice is dangerous, and the operating experience most VCs are missing Why cutting the bottom 10% every year is a fear-based McKinsey relic that doesn’t fit a winning org Everyone is working harder than ever, and why staying enabled on AI now takes nights and weekends The $100M exec packages at the top, and the K-shaped split forming across the market Why seat-based pricing is dying, and what consumption means for top-down vs. usage-based sellers Why industry expertise is overrated, the one exception Chris makes, and why a Rolodex hire is worst of all 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 (an advisory, recruiting, investing, and 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 Crew Crew is an advisory, recruiting, investing, and media firm for seed through series C AI-natives and fast-growing SaaS startups.

  • June 30 · 58 min

    Sales Mafias & What Made MongoDB Great w/ Graham Moreno, VP Worldwide GTM @ Parallel

    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 mafia" that's produced a remarkable share of today's best GTM leaders. He got his start, somewhat by accident, at Oracle straight out of college. He's a self-described enablement obsessive, a Delta loyalist, and a believer that the people you work with matter more than the product you're selling. 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 (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 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/crewgtmYouTube: https://www.youtube.com/@thecrewgtmNewsletter: https://www.withcrew.blog/Website: https://www.withcrew.ai/ This episode is brought to you by the following sponsors: Salesgraph Enterprise deals don't usually slip because of effort - they slip because the technical gap didn't get caught in time. A champion goes quiet, an objection never got handled, procurement shows up late. That context lives in your calls, Slack threads, and top reps' heads, and it doesn't transfer when you hire. Salesgraph pulls from your Salesforce, Gong, Granola, docs, and Slack, then writes the things that move deals forward - gap analyses, champion business cases, and pre-call briefs. It's like a company-specific GTM brain. YC-backed, built by founders who lived this at Mintlify. Get a free GTM audit → salesgraph.com/gtm-audit Dust AI has made individual GTM work faster. But it hasn't made GTM teams more coordinated. Too much work still happens in silos. One person, one agent, one threat at a time. Dust gives teams of humans and agents a shared workspace to move complex go-to-market work forward using the right model for the job. Think account command centers, RFP deal rooms, and cross-functional launches. Instead of keeping AI work trapped in threads, Dust makes agents part of how your team coordinates makes decisions and drives work. That's multiplayer AI, and that's Dust. Check it out at: https://dust.tt/ Centralize If you work complex enterprise deals, the hard part is an effort, it's visibility. Who we met with on this account? Who's gone quiet? Who's on my team who can open a door that we haven't knocked on yet? Centralize answers all three of those questions. It builds a live stakeholder map for every deal, pulling from Salesforce, email calls, and your team's networks and then telling you where to go next. Teams at LangChain, Decagon, Webflow, and Cognition run on it. Try it on a live deal now at usecentralize.com.

  • June 23 · 1 hr 1 min

    How We're Building Granola Into the Most Beloved Product in AI w/ Bardia Shahali, VP Sales @ Granola

    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 Fireworks at Series A and helped scale it, before landing at Granola. Along the way, he's advised a number of 0-to-1 companies building their first go-to-market engine. He met his wife at Intercom, sold his house and moved his family (plus two dogs) back to SF so he wouldn't miss the AI wave, and talks into Wispr Flow so much his wife says it's "what old people do." He's also a prolific writer on sales and GTM, and once got rejected from his dream MBA program and decided to go build startups instead. Timestamps (00:00) Intro (01:22) Welcome to the Crew Podcast + Sponsor (02:47) Granola: One of the Most Beloved Products in Tech (03:13) The Booth Rejection & Bardia's Career Arc (06:18) Moving Back to SF for the AI Wave (08:03) What Actually Makes Granola Special (10:31) Is the Entry-Level Sales Role Dead? (12:06) Killing the Busywork, Not the Job (Claude Co-Work) (18:29) Build Your GTM Org Around Your Sales Cycle (24:22) Why $100M ARR Doesn't Mean What It Used To (26:42) The Hiring Mistake That Wrecks AI Companies (32:38) The AI Tools Bardia Can't Live Without (35:34) The Steak Dinner Is Dead (40:13) How To Choose the Right Company in AI (45:23) Founder-Market Fit, Market Pull & TAM (48:10) Interviewing for Mindset Over Mechanics (49:39) The Outreach That Stood Out (52:10) The GTM Orgs Bardia Admires (Figma & Cursor) (54:11) The "Order Taker" Debate (57:27) Why 90% of AI Unicorns Are in SF (01:00:56) Granola's Roadmap & What's Next 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 (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 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 Newsletter: https://www.withcrew.blog/ Website: https://www.withcrew.ai/ This episode is brought to you by Salesgraph. Enterprise deals don't usually slip because of effort - they slip because the technical gap didn't get caught in time. A champion goes quiet, an objection never got handled, procurement shows up late. That context lives in your calls, Slack threads, and top reps' heads, and it doesn't transfer when you hire. Salesgraph pulls from your Salesforce, Gong, Granola, docs, and Slack, then writes the things that move deals forward - gap analyses, champion business cases, and pre-call briefs. It's like a company-specific GTM brain. YC-backed, built by founders who lived this at Mintlify. Get a free GTM audit → salesgraph.com/gtm-audit

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