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. 3d ago

    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 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/

  2. Aug 11

    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/

  3. Aug 6

    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/

  4. Aug 4

    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 CROThe App Dynamics SKO that made him fall in love with salesThe "value pyramid": why great sellers talk about the customer's company, not their ownHow App Dynamics scaled from $120M to $700M ARR without the best productThe 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 waveThe coachability red flag he watches for in the first interviewWhy he joined Vercel: how people will design and build in the AI eraSignal-based GTM and turning plug motion and open-source momentum into enterprise dealsBuilding Athena, Vercel's homegrown GTM engineWhy 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/

  5. Jul 28

    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 decisionThe best way to use AI in GTM: Waste Management's green-dumpster play and the Tide sentiment workflowBuilding a pipe-gen muscle before the inbound music stops Why "how much pipeline do you self-source?" is a useless interview questionThe mock-call-plus-deal-debrief that replaced the memorized product demoSpike in product or spike in sales: how Clay hires when there's no playbook yetNo variable comp, on purpose and the signal that it's time to switch it onThe 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 AIThe 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/

  6. Jul 21

    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 forecastSelling to users vs. buyers, and to marketers vs. developersThe number one trait she screens sellers for: mental resiliencyHiring "spikes" over generalists to raise the whole team's ceilingScrapping the job title to hire in the AI-native eraThe mock discovery call and the feedback round that actually decides itWhy personalization is about the buyer's problem, not their alma mater, and why the phone call still convertsHow the best talent leaders are becoming business strategistsWhy 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/

  7. Jul 14

    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 allyThe 1% move: candidates who learn the product and demo it back to youCompany selection as a concentrated VC bet: TAM, founders, and real customer loveWhy enterprise is a conviction test most companies fail at the 90-day markThe pricing tell: if you're only losing on price 10–15% of the time, you're too cheapLogos over margins early, and why ten enterprise logos beat the deal economicsThe MEDDPICC-as-activity method, and the rep who taught Claude to run itWhy in-person sales came back, and why the human is the differentiator when everyone has AIThe ten-second LinkedIn scan: trajectory, job-hopping, and builder DNABreaking in when you don't fit the rubric — earn your way up the mountain"No champion, no deal" applies to hiring as much as sellingToken-maxing vs doing more with lessTimestamps: (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 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/channel/UC-rcm2qdgF22H2th_KhrlxgNewsletter: https://www.withcrew.blog/Website: https://www.withcrew.ai/

  8. Jul 7

    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.

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Ratings & Reviews

5
out of 5
8 Ratings

About

The Crew Podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, co-founder @ Crew (a GTM recruiting, media, & investing firm for seed through series D AI-natives) sits down with operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today. No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts. Find us @ https://www.withcrew.ai/ & https://www.withcrew.blog/

Information

  • Creator
    Crew
  • Years Active
    2025 - 2026
  • Episodes
    39
  • Rating
    Explicit
  • Copyright
    © Crew
  • Show Website
    The Crew Podcast

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