The Crew Podcast (fka The Vibescaling Podcast)

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/

The Crew Podcast (fka The Vibescaling Podcast) is a technology podcast hosted by Crew, with 39 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Crew hosts The Crew Podcast (fka The Vibescaling Podcast), a technology show with 39 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  The Crew Podcast (fka The Vibescaling Podcast)

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

  Aug 18, 20261h 2m

  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/

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  The Crew Podcast (fka The Vibescaling Podcast)

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

  Aug 11, 202656 min

  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 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. 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/

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  The Crew Podcast (fka The Vibescaling Podcast)

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

  Aug 4, 202649 min

  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/

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  The Crew Podcast (fka The Vibescaling Podcast)

  How the Top 1% Land Sales Offers in 2026 w/ Chris Balestras, Co-founder @ Crew

  Aug 3, 202654 min

  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/

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  The Crew Podcast (fka The Vibescaling Podcast)

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

  Jul 28, 20261h 1m

  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/

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