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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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  • 22 episodes
  • weekly
  • Avg 53 min
  • English

Episodes 22

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  • Tuesday · 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

  • June 16 · 56 min

    How To Hire Sales Reps Like a Moneyball GM W/ Navid Zolfaghari, Chief Sales Officer @ Zapier

    Navid's Background Navid Zolfaghari is the Chief Sales Officer at Zapier, where he's leading the push to move one of PLG's most iconic companies up-market into the enterprise. Before Zapier, Navid spent six years at Branch, joining at roughly $500K in revenue and helping scale it to ~$100M. He then went to Metronome to go deeper on usage-based pricing. Early in his career, he was at a retail analytics startup and before that he co-founded a company focused on micro-location data and beacons. Navid got his start at Wildfire, which he joined at ~20 people and watched grow to 400 people before it was acquired by Google. He spent a couple of years at Google post-acquisition, which was plenty long enough to learn that the big-company lifestyle wasn't for him. He's also a poker player, a Miami Heat loyalist, and shamelessly pours his milk before cereal (yes, we think it’s crazy too). Timestamps (00:00) Intro & Why Navid Made the Trip from Redwood City (11:16) Navid's Background: Two-Time Founder to GTM Leader at Wildfire, Branch, Metronome & Zapier (13:07) The Google Acquisition Story & Knowing Big Company Life Wasn't for Him (15:00) What Zapier Actually Is Now: Agents, MCP & the Evolution Beyond Hand-Rolled Zaps (15:35) AI Fluency at Zapier: The Four-Tier Rubric & Why "I Use ChatGPT" Is Now Unacceptable (21:34) The War Council: An AI Advisory Board the Entire Exec Team Uses (23:38) How Zapier Fits Into the MCP & Claude Co-Work Era (34:43) Most Common Personas & the Rise of the "Head of AI Transformation" (36:22) The Unified Value System: How One AE Replaced an Entire Sales Value Engineering Function (38:36) Tools You'd Have to Rip From His Cold Dead Hands (42:03) The Blueprint for Excellence: Startup Fit, Business Athleticism & Purposeful Drive (53:57) Love to Win vs. Hate to Lose: How He Evaluates Competitive Drive (01:05:28) The Consultant Mindset: What's Actually Changed in the Sales Archetype 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/vibescaling/https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxghttps://www.youtube.com/@thecrewgtm Newsletter: https://www.vibescaling.blog/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

  • June 9 · 1 hr

    How The Best Salespeople Are Building Agents in GTM w/ Roy Mathew, Head of Sales @ Gumloop

    Roy’s Background Roy Mathew is the Head of Sales at Gumloop, one of the leading AI agent builders helping companies automate workflows across sales, marketing, and IT. Before Gumloop, Roy spent several years at Airtable where he started as a growth lead, pitched the CEO to let him carry a bag, and helped build the sales playbook from scratch. After Airtable he followed his former head of sales to Recurrency, an ERP-adjacent platform selling into distributors and wholesalers. Before all of that, Roy was a special situations options trader, worked on the marketing team at Box, co-founded an automotive technology company called UQuote, and did a stint at Elastic. He's a Harvard undergrad, Wharton MBA, and has one of the more unconventional paths into sales leadership you'll hear. Timestamps: (00:00) Intro & The Sell-Grill-Sell Sandwich: Why Hiring Managers Kill Their Own Pipeline (02:39) Roy's First Call Horror Story: Getting Deal-Reviewed for a VP Role (04:55) From Options Trader to Box to Founding a Company: Roy's Roundabout Path Into Sales (09:47) Joining Airtable as Employee 25: How a Guy Looking Over His Shoulder Changed Everything (11:04) Pitching the CEO: "Let Me Carry the Bag or I'm Just the Spreadsheet Person" (14:46) How to Evaluate an Early-Stage Company: Beyond the Investor Logos (17:58) Why He Chose Gumloop: The Two-Week Interview That Threw His Framework Out the Window (20:17) MCP, Co-Work, and the Agent Era: A Non-Technical Explainer (26:06) The Blank Page Problem: How Gumloop Thinks About Personas vs. Use Cases vs. Industry (31:00) The Pre-Call Agent Stack: Email, Slack, Gong, Granola, and Web Scrapers in One Brief (35:34) The Post-Call Agent Stack: Recap Emails, CRM Updates, Linear Tickets, and Product Feedback (38:03) The Self-Improvement Loop: An Agent That Watches What You Actually Send (42:30) Agents for Sales Leaders: Process Adherence, Pipeline Inspection, and SPICED Monitoring (50:40) GTM Mafias: Why the Slack Mafia Might Be Overhyped (52:21) Blue-Chip-Only Resumes Are a Red Flag: "You Want Someone Dangerous at a Bad Company" (57:15) The Outbound Play That Actually Works: Gumball Machines and Speaking Like a Human (59:35) What Roy Looks For When Hiring at Gumloop Right Now 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/vibescaling/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

  • June 2 · 57 min

    Every Startup Is Lying to You, So Here's How to Pick the Right One w/ Glenn Rachlin

    Glenn Rachlin is the VP of Worldwide Sales at Blockaid, a cybersecurity company protecting the blockchain and crypto ecosystem from malicious attacks. Before Blockaid, Glenn was an early sales hire at Alchemy, the infrastructure layer for crypto, where he helped grow the company from a $500M valuation to $10B and scaled the team from 10 to 130. Prior to his startup chapter, Glenn spent years at AWS during its era of dominance, where he experienced the wild "horse trading" culture of swapping accounts and reps between territories. He cut his teeth earlier at EMC (the classic 1980s sales org with Wolf of Wall Street energy) and IBM (old school, multi-generational, consulting DNA). Glenn is a Long Island native, a Bitcoin maxi who dollar-cost-averages into the ETF, a student of the Hunters and Unicorns podcast lineage, and a member of the Cyber Startups Network VC group. Timestamps (00:00) Intro (01:03) Glenn's Background: IBM → EMC → AWS → Alchemy → Blockaid (02:20) Why He Left AWS After Years at the World's Hottest Company (03:47) Cold-Calling CROs From Podcasts and Forcing Them to Be His Advisors (05:03) Getting Rejected by AWS Twice: The Loop Interview and What It Takes (06:53) Why Big-Company Reps Struggle at Startups (The Two-Sale Problem) (08:06) The "Order Taker" Debate: When Easy Mode Is Actually the Smart Move (09:58) Horse Trading at AWS: Swapping Accounts and Reps Like Sports Trades (12:07) Sales Orgs Glenn Admires Most: Scale AI, Wiz, Datadog, Snowflake (18:09) How to Choose the Right Startup: Founder Pedigree and Backchannel Everything (19:49) Every Startup Is a Complete Shit Show (And That's the Point) (25:28) Assessing Market Pull Before You Join (28:59) The Chainalysis Story: $100M to $8B Because of One Regulation (30:55) AI in Sales: Translating Hebrew in Slack and Vulnerability-Based Prospecting (32:35) Why Israeli Military Intelligence Breeds the Best Startup Founders (39:01) How AI Is Changing the Sales Profile and Quota Expectations (42:30) Why You Can't Hire Slow and Win(46:43) Glenn's Hot Take: If You Didn't Get the Job, You Didn't Try Hard Enough (50:15) What Doesn't Work in Sales Anymore: Remote Is Dying, Cold Calling Is Back (53:07) Bitcoin, Dollar-Cost Averaging, and Where Glenn Puts His Money (54:41) Creative Ways to Get in Front of Anyone (Without Being Weird) 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/vibescaling/https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxghttps://www.youtube.com/@thecrewgtm Newsletter: https://www.vibescaling.blog/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

  • May 26 · 49 min

    How Harvey Scaled GTM to an 11B Valuation w/ Rob Saliterman, VP of Sales @ Harvey

    Rob’s Background Rob Saliterman is the VP of Sales at Harvey, the AI platform for legal professionals that's grown from two customers to a $11B valuation in under two years. Before Harvey, Rob spent five years at Stripe leading teams focused on B2B vertical software platforms. Prior to that, he held sales and leadership roles at Snapchat and Google, where he got his start running political advertising sales after a career in government, including time in the White House. Rob got into sales through an unlikely door: Google needed someone who understood politics and could learn digital marketing. He'd never carried a bag before. He has an MBA from Harvard Business School and is one of the few people in AI sales leadership who came up through government and political communications rather than traditional SaaS. Discussed In This Episode Why he cold messaged Harvey's co-founder on LinkedIn after reading an OpenAI portfolio list (and how he got a reply) Hiring a VP of Sales before hiring AEs: why Harvey did it backwards on purpose The interview question that gives the most signal: "Walk me through a big deal: how you created it, converted the champion, and closed it" Selling to lawyers who've never bought software before and why testing for non-technical communication matters more than legal expertise No champion, no deal (except when it's worth it to slog through without one) Why pipe gen is a muscle memory sport and the first thing reps deprioritize when they shouldn't Personalizing demos using a lawyer's own public filings and why lawyers lean in when you give them something to argue with Hiring management consultants alongside AEs to solve the change management objection The managing partner test: why consistency and credibility matter more than polish How Harvey went from five PDFs you could ask questions about to a collaboration platform with 1,000+ customers Timestamps (00:00) Intro (07:45) Rob's Background: White House → Google → Snapchat → Stripe → Harvey (08:40) Why He Cold Messaged Harvey's Co-Founder on LinkedIn (10:24) The Moment He Knew Harvey Was Real: A Lawyer's Outside Counsel Test (12:37) Career Path: How a Government Background Translates to Sales (15:16) The Common Thread Across Google, Stripe, and Harvey: Selling Something New (17:14) Hiring a VP of Sales Before AEs: Why Harvey Did It Backwards (21:05) What Makes a Great Harvey AE: Selling to Non-Technical Buyers (27:18) How the Hiring Profile Changed From 10 Reps to 100 (29:59) Pipe Gen at Harvey: Why the Fundamentals Still Work (34:42) Why Pipe Gen Is the First Thing Reps Deprioritize (36:44) Personalizing Demos With a Lawyer's Own Public Filings (40:05) Rev Ops as an Early Hire: Why Harvey Built Infrastructure From Day One (44:34) No Champion, No Deal (Except When It's Worth Breaking That Rule) (49:49) Change Management as a Sales Differentiator (52:00) The Managing Partner Test: Consistency Over Polish (55:19) Where Harvey's Best AEs Actually Come From (58:32) The "Why Now" Interview Question That Separates Good From Great (01:00:00) Wrap + Where Harvey Is Headed 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/vibescaling/ YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg Newsletter: https://www.withcrew.blog/ Website: https://www.withcrew.ai/

  • May 19 · 51 min

    Why The Best Sales Rep You Interview Is Probably Your Worst Hire with Mike Heller, Partner @ Floodgate

    Mike’s Background Mike Heller is a Partner at Floodgate, one of the most respected seed-stage venture firms in Silicon Valley known for early bets on companies like Twitch, Lyft, and Twitter. Before Floodgate, Mike spent four and a half years at Clearbit where he joined as the first sales and marketing hire and helped grow the business from just over $1M to nearly $15M ARR. Prior to that, he was an early enterprise seller at Dropbox during the era when it was a "nearly impossible" sell, competing against free bundled solutions from Google and Microsoft while Box was building everything the enterprise buyer wanted. Mike got his start in Singapore running sales for a test prep business, then got pulled into Dropbox's experimental bottoms-up sales motion before it even had a name. After Clearbit he built a GTM advisory practice working with pre-PMF founders, which eventually led him to the investor seat at Floodgate. Discussed In This Episode Why the Dropbox enterprise sale was so hard and why that difficulty bred an elite generation of sellers The "smooth talker" trap: why the most impressive interview candidate is often your worst hire Why founders hire salespeople too early and what they're actually trying to solve The Jason Lemkin "hire two AEs" rule and when it's completely wrong How Mike grew Clearbit from ~$1M to ~$15M as the first GTM hire Why he stopped wanting to be a sales leader, and what he chased instead How giving free feedback on founder sales calls built his advisory business, deal flow, and investor career The two traits Floodgate looks for before writing a check: speed and "super learning" Why the Wayback Machine is an underrated founder diligence tool Where AI is actually showing up in sales and where it's still not touching the core of the job Timestamps (00:00) Intro (01:35) Mike's Background: Singapore → Dropbox → Clearbit → Floodgate (04:09) What Made the Dropbox Sales Culture So Elite (05:02) Why Selling Dropbox Enterprise Was "Nearly Impossible" (06:01) Leaving Dropbox: Choosing Clearbit Over Slack and Segment (09:58) Growing Clearbit From $1M to $15M as First GTM Hire (11:17) Why Mike Stopped Wanting to Be a Sales Leader (12:48) Building an Angel Investing and Advisory Career (14:37) Common Mistakes Founders Make on Discovery Calls (15:43) When Founders Should (and Shouldn't) Hire Their First AE (18:22) Why Hiring Too Early Creates Bad Revenue (20:22) From Advisory to Floodgate: Choosing the VC Path (25:39) Do Operators Make Better Investors? (27:56) The Two Traits That Matter Before Writing a Check: Speed + Super Learning (30:40) The Wayback Machine as a Founder Diligence Tool (32:15) AI in the Sales Tech Landscape: What's Real and What's Not (36:56) Career Advice: Stop Optimizing for Logos, Chase Energy (40:08) The "Smooth Talker" Trap in Sales Hiring (43:55) Should Founding AEs Get More Equity? (48:13) Why You Shouldn't Optimize Your Fundraise Around a GTM-Focused VC (50:19) The Future of Sales: Reps Who Can Ship Code About The Vibescaling Podcast The Vibescaling podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Vibescaling (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 Vibescaling Vibescaling is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups. Where to Find Vibescaling LinkedIn: https://www.linkedin.com/company/vibescaling/ YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg Newsletter: https://www.vibescaling.blog/ Website: https://www.vibescaling.ai/

  • May 12 · 44 min

    How We Built Profound’s GTM Motion To A $1B+ Valuation w/ Mark Ebert, SVP of Revenue @ Profound

    Mark’s Background Mark Ebert is SVP of Revenue at Profound, the answer engine optimization platform helping brands win in the new world of AI search. Before Profound, Mark spent nearly nine years at 6sense, joining to build out the East Coast sales team. After an eventful day one, including one AE quitting and the remaining one begging him to stay, Mark went on to help build the company into the ABM category leader. Before 6sense, Mark sold and led enterprise teams at Responsys / Oracle Marketing Cloud during the marketing cloud wars against Salesforce and Adobe. He started his career as a BDR at Experian right out of college, after his dad’s sage advice that since he wasn't going to be a doctor or a banker, he should find a way to get into sales. Mark is based in Boston, a history buff with a soft spot for Revolutionary War battle planning, and probably the most relentlessly optimistic sales leader you'll meet. Discussed In This Episode Why enablement teams shouldn't actually be running enablement and who should instead when product ships daily The two questions every new AE at an AI-native company should be obsessed with answering in week one The "leave them alone on the sales floor" test for spotting a sales leader who's actually a doer vs. a dashboard leader Why he'd rather hire the rep who crushed it at the #3 product company than the rep who hit 150% at the obvious category leader What World War 2 battle planning teaches him about running a POC The "see the movie before it plays" framework and how the best reps whiteboard the 3 most likely deal paths and pre-plan their counter-moves Why the B2B sales funnel is collapsing inside of LLMs (and the data on what 80% of buyers do after they leave ChatGPT) Marketing to your new "ultra customer": the LLM itself The Jolt Effect: why most deals die from fear of screwing up, not fear of cost and how to surface that fear before the buyer does AI tooling the team is leaning on right now (Dust, Granola) and how Mark uses an AI sales bot to grade his team's first calls overnight Timestamps: (00:00) Intro, What Profound Is Building & Why Mark Joined (02:14) From Experian BDR to Oracle Marketing Cloud: Why Mark Left for Sixth Sense (07:36) Why Your Enablement Team Shouldn't Run Enablement (13:38) The Two Questions Every New AE Should Obsess Over in Week One (17:05) The Sales Leader Who Won't Sell Is a Liability: The "Leave Them on the Sales Floor" Test (22:21) The 3-Path Whiteboard: How Great Reps See the Deal Before It Plays (23:24) Confidence vs. Overconfidence: The Hire Mark Worries About (27:09) What World War 2 Teaches Mark About Running B2B Evaluations (29:36) Why Hiring from the #3 Product Beats Hiring from the Category Leader (31:30) The Quota Attainment Question Most Hiring Leaders Read Wrong (33:30) The B2B Funnel Is Collapsing Inside ChatGPT (37:31) Marketing to Your New "Ultra Customer": The LLM Itself (38:38) Rapid Fire: Staying Upbeat, Dust, Granola & The Jolt Effect About The Vibescaling Podcast The Vibescaling podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Vibescaling (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 Vibescaling Vibescaling is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups. Where to Find Vibescaling LinkedIn: https://www.linkedin.com/company/vibescaling/ YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg Newsletter: https://www.vibescaling.blog/ Website: https://www.vibescaling.ai/

  • May 5 · 46 min

    Why "AI for Finance" Is Meaningless & Why Bankers Make the Best Sellers W/ James White @ Rogo

    James White is the VP of Sales at Rogo, one of the hottest AI companies in finance, building AI for investment banking and rapidly landing the biggest institutional logos on Wall Street. Before Rogo, James helped build and sell Sentieo (acquired by AlphaSense, now valued at ~$8B), where he sold financial search tools to hedge funds and asset managers. Prior to that, he was an early sales hire at PerfectData (acquired by Nutanix pre-IPO), where he learned enterprise sales from a team of ex-Data Domain reps and helped scale the company from 0 to $20M in ARR. James started his career working at CompUSA in high school, turned down Morgan Stanley to join Apple, and then caught the startup bug and hasn’t looked back since. He's a Houston native who went west to Berkeley with one goal: build companies. Discussed in this episode: Why "AI for finance" is like saying "software for business" (and why both are meaningless phrases) How Rogo sells into MDs at banks who can barely navigate their own tools but have incredible judgment The "Einstein starts at the bank tomorrow" analogy for explaining AI adoption to skeptics Why investment banking's compliance and infosec moat is actually Rogo's moat The GTM Associate program: how Rogo converts burned-out junior bankers into elite sellers Why renaming "SDR" to "GTM Associate" isn't just a branding unlock but a recruiting one too The comp structure pitch that gets bankers to take a pay cut (and why they do it) How Alex Pall from The Chainsmokers became Rogo's most productive SDR Why Rogo's top-performing AE is also the #1 user of Rogo (more than the CEO) Product obsession as the new screening filter in hiring The Renaissance Technologies thesis: take a banker, teach them sales, and watch them dominate Timestamps 00:00 - Cold Open: Why Finance is Deterministic and AI Isn't 01:24 - Intro & James's Origin Story: Stock Picking at CompUSA 03:42 - Breaking Into Tech Sales at Pure Storage 06:34 - Apple, Morgan Stanley & Choosing the Startup Path 08:23 - Joining Sentieo & Selling to Hedge Funds 11:15 - Why Selling AI is Different from Selling SaaS 12:31 - Solving for Hallucinations in High-Stakes Finance 15:18 - Why MDs Are Surprisingly Heavy AI Users 17:24 - Structuring Rogo's Enterprise GTM Team 20:57 - Why Bankers Make Great Salespeople (The Renaissance Thesis) 22:41 - "AI for Finance" is Meaningless: Why Rogo Picked IB 26:01 - Why Anthropic Won't Eat the App Layer 31:14 - Defining the AI-Native Seller 34:33 - Building a Sales Team from Burned-Out Junior Bankers 39:07 - The Chainsmokers' Alex Pall: Rogo's Best SDR 42:16 - Reimagining GTM Workflows with AI 45:38 - What Rogo is Hiring For About The Vibescaling Podcast The Vibescaling podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Vibescaling (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 Vibescaling Vibescaling is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups. Where to Find Vibescaling LinkedIn: https://www.linkedin.com/company/vibescaling/ YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg Newsletter: https://www.vibescaling.blog/ Website: https://www.vibescaling.ai/

  • April 28 · 55 min

    The Old Sales Playbook Is Dead: Hiring + Selling In The AI Era w/ Jacquelyn Goldberg, VP Sales @ Unframe AI

    Jacquelyn's Background Jacquelyn Goldberg is the VP of Sales at Unframe, which has been dubbed the "Palantir for AI.” Unframe works with Fortune 500 companies to identify business problems worth solving and ship production-ready solutions to them in days, not months. Before Unframe, Jacquelyn was the VP of Global Revenue at Sama AI. She spent most of her career in machine learning-adjacent startups as an early go-to-market hire, then pivoted fully into AI about five years ago, before most salespeople had even heard the term artificial intelligence. She's an early-stage lifer who's built GTM at companies before their sales playbook exists, and has been in the arena long enough to know which hires actually work and which ones just can interview well. Timestamps (00:00) Intro & What Unframe Does (Palantir for AI) (05:50) Why Every AI Startup Sounded the Same & How Jacquelyn Evaluated Defensibility (08:05) Industries Adopting AI Fastest (Real Estate, Financial Services, Healthcare) (09:20) How Unframe AI Lands & Expands Inside Enterprise Accounts (10:50) The 50% Assessment Failure Rate & What Candidates Keep Getting Wrong (13:40) Discovery as a Give-Get, Not an Interrogation(15:55) What Jacquelyn Actually Means by Intellectual Curiosity and Grit (18:25) Following the Cookie Trail: How to Show Curiosity in an Interview (20:25) Can You Teach Discovery? What's DNA vs. Trainable (23:05) AI Literacy Tiers: From Not Using It to Vibe Coding (25:15) How to Prove Grit When You've Never Worked at a Startup (26:45) "It Functioned Like a Startup" and Why That's Not the Same Thing as One (28:25) Most Pipeline Problems Are Actually Thinking Problems (31:10) What's Actually Working in Outbound Right Now (32:55) The Rolodex Is the Lowest Thing You Should Hire For (34:45) Industry Expertise: When It Matters and When It Doesn't (37:00) Radical Honesty: Telling Candidates Every Reason Not to Join (38:40) Two Weeks Feels Like Six Months at the AI Company Pace (40:00) Why Big Company Reps Struggle at Startups (It's Not Talent) (43:35) How Enterprise Selling Changed Post-COVID (47:50) Is Sales Dead? Why AI Makes Sellers Better, Not Obsolete (49:20) The Future of Entry-Level Sales & Why Universities Need to Catch Up (51:50) Alpha School and Rethinking How People Find Their Career About The Vibescaling PodcastThe Vibescaling podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Vibescaling (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 VibescalingVibescaling is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups. Where to Find Vibescaling LinkedIn: https://www.linkedin.com/company/vibescaling/ YouTube: https://www.youtube.com/channel/UC-rcm2qdgF22H2th_Khrlxg Newsletter: https://www.vibescaling.blog/ Website: https://www.vibescaling.ai/

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