Explorez tous les épisodes du podcast The Crew Podcast
| Titre | Date | Durée | |
|---|---|---|---|
| Why Inference Is the Hottest Market in AI Sales Right Now | Soumya Tulloss, SVP Sales @ Fireworks AI | 03 Nov 2026 | 00:50:47 | |
Soumya Tulloss is SVP of Sales at Fireworks AI, one of the fastest growing AI-native companies out there, fresh off a Series D at an $18B+ valuation. She joined earlier this year when the go-to-market team was about 20 people. Before that she spent seven years at Twilio, joining when the company was around $89M in revenue and proud of having no sales team, then helping build the enterprise motion that took it from hundreds of millions to billions. She came up through finance at Deutsche Bank and biz ops before saying yes to sales, starting as an AE and never looking back. Her take on the market right now: inference is the oxygen of the modern enterprise, and you can't scale if you're spending more on inference than you generate in revenue. Timestamps: • (00:00) You can't scale on inference you can't afford • (01:20) Welcome to the Crew podcast • (02:21) Why inference is the oxygen of the enterprise • (04:48) Where inference sits in the AI stack • (07:03) Cost versus owning your AI stack • (09:23) Competing with the frontier labs • (11:42) From Deutsche Bank and biz ops to sales at Twilio • (14:44) How she chose Fireworks • (17:55) The FIRE way of selling • (21:26) Being first to production in a deal • (24:34) What Fireworks looks for in technical sellers • (28:36) Selling AI at the CEO and board level • (32:13) Why the labs don't pay variable comp • (35:03) Role plays and hiring lessons • (38:18) The agents running Fireworks' GTM team About The Crew Podcast Every week, host Chris Balestras, partner @ Crew, talks to the people actually building go-to-market motions in real time, not in retrospect. About Crew This Episode Is Brought To You By Metaview: The agentic recruiting platform, built for hiring end to end. Metaview's agents source and reach out to candidates in your own tone, review every inbound application against your criteria and tell you exactly why someone made the shortlist, join every call and deliver structured notes the moment it ends, and surface trends across your pipeline from salary expectations to AI fluency. Recruiters, hiring managers and agents all work off one layer of context, with permissions and a full audit trail behind every output. Trusted by Deel, Brex, Deliveroo, Replit and thousands of other teams. Start for free at https://www.metaview.ai/ Where to Find Crew LinkedIn: https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Website: https://www.withcrew.ai/ Blog: https://www.withcrew.blog/ | |||
| How to Build a Sales Team With No Sales Engineers w/ Steven Boone, VP of Enterprise GTM @ Perplexity | 27 Oct 2026 | 00:53:32 | |
Steven Boone is VP of Enterprise at Perplexity, where he joined about five months ago and now runs sales, customer success, consumer and enterprise support, forward deployed engineering, and rev ops. He got there without ever carrying a bag. After starting out in law school, he moved through product marketing and rev ops, served as chief of staff to the CRO at Twilio, and ran go-to-market at a seed-stage legal tech startup before leading enterprise sales at Zuora, a deliberate jump from Twilio's product-led motion into top-down deals. Since he arrived at Perplexity, every rep he has hired has closed a deal in their first 30 days. Timestamps: • (00:00) Clarity of thought over everything • (01:38) Welcome to the Crew podcast • (03:12) A nontraditional path to the revenue seat • (06:10) Turning support tickets into sales opportunities • (09:51) What Perplexity sells, from search API to Computer • (17:58) Leaving product-led Twilio for top-down Zuora • (20:08) Leading enterprise reps without carrying a bag • (22:25) Productize it or white glove it • (26:09) Complexity versus margin-adjusted ACV • (28:13) Kill the first discovery call • (31:44) Torn apart by AI • (36:12) Why Perplexity has no sales engineers • (42:36) How he interviews for clarity of thought • (46:54) Green, yellow, red capacity planning • (52:03) Why he said yes to sales About The Crew Podcast Every week, host Chris Balestras, partner @ Crew, talks to the people actually building go-to-market motions in real time, not in retrospect. About Crew This Episode Is Brought To You By Metaview: The agentic recruiting platform, built for hiring end to end. Metaview's agents source and reach out to candidates in your own tone, review every inbound application against your criteria and tell you exactly why someone made the shortlist, join every call and deliver structured notes the moment it ends, and surface trends across your pipeline from salary expectations to AI fluency. Recruiters, hiring managers and agents all work off one layer of context, with permissions and a full audit trail behind every output. Trusted by Deel, Brex, Deliveroo, Replit and thousands of other teams. Start for free at https://www.metaview.ai/ Where to Find Crew LinkedIn: https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Website: https://www.withcrew.ai/ | |||
| This Week in GTM w/ Glenn Rachlin (OpenRouter) | Factory vs Cognition, AI GTM Talent Density, & More | 22 Oct 2026 | 00:51:08 | |
Glenn is the Head of Strategic GTM at OpenRouter, an AI infrastructure platform that helps businesses access and route requests across AI models, optimizing for factors like cost and performance.
About The Crew Podcast
Where to Find Crew LinkedIn: https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Website: https://www.withcrew.ai/ Blog: https://www.withcrew.blog/ | |||
| From Yale Engineer to 3 IPOs: How to Hire the Right Rep for Your Sale | Rich Liu, ex-Navan CRO | 20 Oct 2026 | 00:53:17 | |
Most companies hire sales reps from the hottest logos and hope they work out. Rich Liu has built sales teams at Meta, MuleSoft and Navan, and his rule is to hire for the sale you're actually running. In this episode he breaks down how MuleSoft turned hiring into religion, why a great rep can fail in the wrong motion, and how Navan rebuilt its go-to-market when COVID took travel revenue to almost nothing. Rich's Background Rich Liu is a go-to-market advisor to AI-native companies and the former CRO at Navan (formerly TripActions), where he helped rebuild the business through COVID and on to an IPO. Before Navan he ran enterprise sales at MuleSoft, leading a team of a couple hundred people across six offices as the company went from roughly $800M in valuation to a 10x in three years. He joined Meta when it had around 2,000 employees and ran sales and account management teams as it scaled to 20,000. A Yale engineer by training, he got his start in a sales boiler room cold-calling for Fisher Investments after 9/11. Timestamps • (00:00) Cold open • (01:19) Welcome to the Crew podcast • (03:12) From Yale engineer to a sales boiler room • (05:47) Breaking into Meta • (08:24) Leaving Meta for a company named after a farm animal • (12:15) The MuleSoft pivot • (16:49) When hiring became religion • (22:38) Why you can't raise the bar later • (25:19) Know the sale before you interview • (27:45) The Vans store BDR • (37:39) Selling travel during a pandemic • (43:58) Advising AI-native companies • (45:57) Chasing Anthropic-level growth • (49:45) Which sales orgs produce the best reps About The Crew Podcast Every week, host Chris Balestras, partner @ Crew, talks to the people actually building go-to-market motions in real time, not in retrospect. About Crew This Episode Is Brought To You By Metaview: The agentic recruiting platform, built for hiring end to end. Metaview's agents source and reach out to candidates in your own tone, review every inbound application against your criteria and tell you exactly why someone made the shortlist, join every call and deliver structured notes the moment it ends, and surface trends across your pipeline from salary expectations to AI fluency. Recruiters, hiring managers and agents all work off one layer of context, with permissions and a full audit trail behind every output. Trusted by Deel, Brex, Deliveroo, Replit and thousands of other teams. Start for free at https://www.metaview.ai/ Where to Find Crew LinkedIn: https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Website: https://www.withcrew.ai/ | |||
| Why Most AI Startups Aren't Defensible & Why Sales Teams Fail w/ Brendon Cassidy, Founding GTM @ LinkedIn | 13 Oct 2026 | 00:54:40 | |
Brendon Cassidy is the founder of Cassidy Ventures, where he operates, advises, and invests in startups, helping founders with everything from demand and pipeline to their first VP of Sales hire. He was one of LinkedIn's earliest employees, then ran sales at EchoSign alongside Jason Lemkin through its acquisition by Adobe, and later at Talkdesk. He was involved with Gong from its inception and has worked with 100 to 150 companies across SaaS and AI, including Higgsfield AI. He started his career in recruiting and got out after a mentor told him that if you stay in recruiting long enough, you're a recruiter. Today he spends his time as a sounding board for founders and CEOs making the hires that shape their go-to-market. Timestamps • (00:00) Intro • (01:00) Welcome to the Crew podcast • (02:22) From LinkedIn to EchoSign to Gong • (06:42) Why hiring more AEs won't fix demand • (08:34) How the best companies create demand • (10:22) Advisory boards and warm intros • (16:34) Why resumes don't tell the whole story • (20:16) When to run a live role play • (22:46) Salespeople are pathological liars • (25:56) How to pick the right company to join • (28:20) Why 95 out of 100 startups won't make it • (30:59) The problem with secondaries: Ramp vs. Brex • (37:31) CPQ and contracts in a usage-based world • (40:21) AI can't fix product market fit • (42:50) The game film idea for hiring sales • (49:41) The sales mafias he respects • (53:49) Radical meritocracy and promoting from within • (01:00:00) The bootstrapped company that surprised him About The Crew Podcast Every week, host Chris Balestras, partner @ Crew, talks to the people actually building go-to-market motions in real time, not in retrospect. About Crew This Episode Is Brought To You By Metaview: The agentic recruiting platform, built for hiring end to end. Metaview's agents source and reach out to candidates in your own tone, review every inbound application against your criteria and tell you exactly why someone made the shortlist, join every call and deliver structured notes the moment it ends, and surface trends across your pipeline from salary expectations to AI fluency. Recruiters, hiring managers and agents all work off one layer of context, with permissions and a full audit trail behind every output. Trusted by Deel, Brex, Deliveroo, Replit and thousands of other teams. Start for free at https://www.metaview.ai/ Where to Find Crew LinkedIn: https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Website: https://www.withcrew.ai/ | |||
| Cyber Risk Has Never Been Higher & Selling Cyber 101 w/ Steve Pascucci VP of Global Sales @ Outtake | 06 Oct 2026 | 00:53:49 | |
Steve Pascucci is VP of Global Sales at Outtake, the Series B, AI-native security company building a trust layer for the internet. Backed by CRV and ICONIQ and recently named a Forbes Next Billion-Dollar Startup, Outtake protects the world's most recognizable brands and executives from impersonation and threats across the public internet, social media, and the dark web. Before Outtake, Steve spent nearly a decade at Cloudflare, where he was the first outside sales leader hired, helped build its first sales teams, led the push into enterprise, and then built out the global go-to-market for its Zero Trust product. Earlier in his career he built new hire enablement at govtech company Granicus. He grew up in Port Washington, Long Island, and is now based on the West Coast. Timestamps: • (00:00) Welcome to the Crew podcast • (03:22) Why CVEs spiked almost 10x • (06:38) Pixel-perfect impersonations at machine speed • (07:58) Tying your deal to a corporate initiative • (10:36) Why security sells through the channel • (15:33) Selling middle out • (16:59) The champion in the corner of the room • (19:30) Creating urgency without ambulance chasing • (22:45) What's working in outbound • (25:07) Lessons from a decade at Cloudflare • (27:51) Why he always took the harder path • (31:44) Leaving Cloudflare for Outtake • (35:17) Hiring red flags and the AI question • (40:52) How the sales team uses AI agents • (42:21) Blocking AI for new hires in month one • (45:07) Enablement that starts with the Magna Carta • (49:14) Budget cycles and convening power • (53:59) Why he admires the number two players • (57:03) Inside the Outtake sales culture About The Crew Podcast The Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies.Every week, host Chris Balestras, partner @ Crew, talks to the people actually building go-to-market motions in real time, not in retrospect. About Crew Crew is a recruiting, investing, & media firm for seed through series D AI-natives & fast-growing SaaS startups. This Episode Is Brought To You By Attention: Put a team of revenue agents on every deal. Attention captures every customer interaction without a bot in the room, updates your CRM, automates your reporting, scores reps and opportunities against any framework, and forecasts in a way you can actually trust. Trusted by Lovable, Abridge, Avoca, and hundreds of other fast-growing companies. Try it at https://www.attention.com/ Metaview: The agentic recruiting platform, built for hiring end to end. Metaview's agents source and reach out to candidates in your own tone, review every inbound application against your criteria and tell you exactly why someone made the shortlist, join every call and deliver structured notes the moment it ends, and surface trends across your pipeline from salary expectations to AI fluency. Recruiters, hiring managers and agents all work off one layer of context, with permissions and a full audit trail behind every output. Trusted by Deel, Brex, Deliveroo, Replit and thousands of other teams. Start for free at https://www.metaview.ai/ Where to Find Crew LinkedIn: https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Website: https://www.withcrew.ai/ Blog: https://www.withcrew.blog/ | |||
| Live Podcast: The GTM Rebrand, CRO Musical Chairs & Talent Mafias @ Reserve Padel NYC | 01 Oct 2026 | 01:03:08 | |
Live from Hudson Yards: Crew's first-ever live podcast, recorded at the AI GTM Paddle Club Event at Reserve with roughly 150 of New York's best GTM operators in the room. Crew's twelfth event in two years, and the first one on a padel court. The Panel Curt Clauss, Partner at Crew, heading up the AE and sales leadership practice. Twelve years in tech sales across Series A through E, including runs at Harvey and Outreach, plus founding AE experience. Matthew Roberts, Crew's SDR leadership practice, three months in. Ten years in SDR leadership, and hiring was always his favorite part. Caitlin Desai, Co-founder at Crew, running exec recruiting. Seventeen years as a GTM IC and leader at Bay Area companies including Box and Dropbox, and watched a company go from $1M to $1B in ARR. Plus drop-ins from Mark Ebert of Profound and George of Basis, Head of GTM. Discussed in This Episode: - Why Paul Graham thinks “GTM” sounds bogus, and why Crew is doubling down with 200 hats - The Stripe origin story of the GTM rebrand, and why every AI native inherited it - CRO musical chairs at the labs: Paul Smith, Denise Dresser, and Dolly's arrival - How Wiz ran the equivalent of a six-to-twelve-month enterprise sale in six days - Curt's 80/20 for vetting a startup AE role: tier one investor, inbound mix, real product market fit - Read the wins channel. Cobwebs and crickets tell you what the pitch won't - Andy Kofoid's four-to-five-year rule, and why it lacks nuance for startup operators - The three reasons people actually stay: quota, learning, equity - Commission breath: are the best reps coin operated, or is it the story behind the answer? - Prep, don't creep. Green flag if you did the research, red flag if you're weird about it - GTM mafias: Stripe, MongoDB, Metronome, Slack, Segment, Listen Labs, Cursor - Mark Ebert on Profound's pivot from single-product to multi-product, and training a team running 150 miles an hour Timestamps - (00:00) Live from Hudson Yards: Crew's first live podcast - (05:00) Paul Graham vs. the GTM rebrand - (11:00) CRO musical chairs at OpenAI and Anthropic - (15:00) How Wiz ran a six-day enterprise deal - (20:00) Mark Ebert on Profound's pivot to multi-product - (29:00) The 80/20 of picking a startup AE role - (31:30) Read the wins channel before you sign - (39:00) Andy Kofoid's four-year rule, and why Chris disagrees - (45:30) Are the best reps coin operated? - (55:30) GTM mafias: Stripe, Mongo, Metronome, Cursor About The Crew Podcast Every week, host Chris Balestras, partner @ Crew, talks to the people actually building go-to-market motions in real time, not in retrospect. About Crew Where to Find Crew LinkedIn: https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Website: https://www.withcrew.ai/ | |||
| GTM Roundtable: The State of AI-Native Sales w/ Clay, Parallel, Avoca & Profound | 29 Sep 2026 | 01:31:14 | |
Four sales leaders running revenue at AI-native companies sat down with Chris Balestras to talk about what the job actually looks like right now. Territory plans that get thrown out mid-year. Comp models nobody has figured out. And the thing candidates never hear before they sign, which is that the first year is going to hurt. The conversation runs through deal caps and inbound throttling, why a four-month paper process feels broken to founders who watched the eval close in two days, and how each of them decides whether a candidate wants to learn the game or just extract from it. It closes somewhere more personal, on the conversations these guys had at home before taking the job. The Guests Liam Mulcahy is Head of Go-To-Market at Parallel. Jack Gashi is VP of Sales at Avoca Mark Ebert is SVP of Revenue at Profound Todd Busler is Head of Sales, Americas Discussed in This Episode: • Why annual territory and capacity planning falls apart when you hire this fast • Which things should stay written in pencil and which need to be written in pen • Deal caps and shutting off inbound to stop reps from sitting on pipeline • Why AE productivity benchmarks are made up right now, and everyone knows it • Jack on why equity is the wrong thing for most AEs to optimize for • The “worst 12 months” preview Clay gives candidates on purpose • Coin-operated vs. money-motivated, and how to tell them apart in an interview • The conversations these leaders had with their spouses before saying yes • Hiring people with young kids as a deliberate advantage Timestamps - (00:00) The worst 12 months of your life - (00:51) Welcome to the Crew podcast - (02:05) Headcount planning heading into next year - (02:50) Why most of the plan is written in pencil - (03:55) The four-month paper process nobody can explain - (11:53) When your best rep is also shipping code - (20:57) Moving the AM function into sales - (21:17) What you actually tell a candidate about quota and club - (24:47) Interviewing AMs and writing the rules as you go - (29:33) How do you do capacity planning right now - (29:55) Why the productivity math doesn't add up - (31:11) Reps turtling on deals - (32:33) Setting a deal cap ten minutes after the meeting - (34:14) It's a race, and what that does to coverage - (44:55) Forget the equity - (48:50) Coin-operated vs. money-motivated - (56:36) Hiring someone with a young kid at home - (61:09) Quality of time, and what the family actually sees - (75:04) The nuclear keys About The Crew Podcast The Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Crew, talks to the people actually building go-to-market motions in real time, not in retrospect. About Crew Crew is a recruiting, investing, & media firm for seed through series D AI-natives & fast-growing SaaS startups. Where to Find Crew LinkedIn: https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Website: https://www.withcrew.ai/Blog: https://www.withcrew.blog/ | |||
| The Science of Sales + Why Founders Hire Sales Too Early w/ Mark Roberge, Stage 2 Capital | 22 Sep 2026 | 00:59:21 | |
Mark Roberge is co-founder and Managing Director at Stage 2 Capital, a VC firm backed by roughly a thousand LPs who are go-to-market operators, including the founding CRO of Snowflake and revenue leaders at Anthropic, OpenAI, Databricks, and GitHub. He was the fourth hire at HubSpot and its CRO, taking the company from zero to 100 million in revenue through its IPO. He teaches entrepreneurial sales at Harvard Business School, a course that had 550 students last year and 70 sales coaches on staff, and he is the author of The Sales Acceleration Formula and The Science of Scaling. All proceeds from the new book go to mental health causes. Timestamps: • (00:00) Welcome to the Crew podcast • (00:58) The keynote that became the book • (02:06) The pattern behind the IPOs and the bankruptcies • (04:01) Hiring sales too early, and the VC treadmill • (05:52) Assessing the blitzscale risk of your category • (06:19) AI customer support versus software for airports • (07:02) Set a hiring pace, not a lump sum in January • (08:38) The dilution trap • (10:02) Twenty bets a decade versus your one • (12:24) Nobody agrees on what product market fit is • (13:26) Value creation, not revenue creation • (15:06) Slack's real North Star metric • (16:04) Go-to-market fit and unit economics • (17:16) The revenue velocity formula • (21:33) What is broken in venture capital • (26:12) How his Harvard sales class found product market fit • (29:39) Why he would hire MBAs right now • (30:41) Scorecard versus vibes • (33:42) The biggest hiring mistake founders make • (38:26) Hiring the startup person • (41:36) "I want them to cheat with AI" • (46:51) Selling time: 12 hours a week to 25 • (48:29) Paying HubSpot reps 25% more instead of hiring • (57:37) Why the book proceeds go to mental health About The Crew Podcast The Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Crew, talks to the people actually building go-to-market motions in real time, not in retrospect. About Crew Crew is a recruiting, investing, & media firm for seed through series D AI-natives & fast-growing SaaS startups. This Episode Is Brought To You By Attention: Put a team of revenue agents on every deal. Attention captures every customer interaction without a bot in the room, updates your CRM, automates your reporting, scores reps and opportunities against any framework, and forecasts in a way you can actually trust. Trusted by Lovable, Abridge, Avoca, and hundreds of other fast-growing companies. Try it at https://www.attention.com/ Metaview: The agentic recruiting platform, built for hiring end to end. Metaview's agents source and reach out to candidates in your own tone, review every inbound application against your criteria and tell you exactly why someone made the shortlist, join every call and deliver structured notes the moment it ends, and surface trends across your pipeline from salary expectations to AI fluency. Recruiters, hiring managers and agents all work off one layer of context, with permissions and a full audit trail behind every output. Trusted by Deel, Brex, Deliveroo, Replit and thousands of other teams. Start for free at https://www.metaview.ai/ Where to Find Crew LinkedIn: https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Website: https://www.withcrew.ai/ Blog: https://www.withcrew.blog/ | |||
| Building GTM Agents Live + The AI-Pilled AE Operating System w/ Nic Siegle, Founding AE @ Dust | 18 Sep 2026 | 01:02:25 | |
Nic's Background Timestamps(00:00) The wrong thing at amazing scale (01:30) Welcome to the Crew podcast (02:31) Why Crew wanted to try a live demo episode (03:56) Nic's background, and what Dust actually is (06:11) The three stages of AI adoption inside companies (07:39) Open source Chinese models, and sitting on top of every model (08:30) The MCP timeline, and when tools started talking to each other (11:25) Was Opus the chasm? (12:54) The core sales use cases, from ask-sales bots to RFPs (17:10) Why "how AI pilled are you" is now an interview question (18:06) How Clay and 1Password govern who builds what (20:51) "Show me something you've built" (22:04) Building a pre-call prep agent from scratch (24:48) Picking a model, and the test that cost 178 times more (31:07) Idiot in motion versus the blast radius of AI (39:03) Setting a 7am trigger and emailing yourself the brief (44:48) Publishing an agent so the whole team can use it (49:26) Nic's cockpit: Pods and an AE operating system (55:36) Building an account plan with org chart and live product usage (01:01:15) Where to try Dust About The Crew Podcast Every week, host Chris Balestras, partner @ Crew, talks to the people actually building go-to-market motions in real time, not in retrospect. About Crew This Episode Is Brought To You By Where to Find Crew LinkedIn: https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Website: https://www.withcrew.ai/ | |||
| The 0 to $20M GTM Traps + How To Diligence A Founder w/ Dini Mehta, Operating Partner @ Peak XV | 15 Sep 2026 | 00:43:10 | |
Dini Mehta is an Operating Partner at Peak XV, where she parachutes into portfolio companies on go-to-market, sits in exec meetings, runs forecast calls, and hosts open office hours for founders and GTM teams across the portfolio. She was CRO at Lattice, where she took the company from $3M to over $100M ARR and from a single product to a platform. Before that she led go-to-market at Drawbridge from pre-revenue to $140M ARR, and got her start in the early programmatic days at Comcast. An immigrant who fell into sales and then into tech, she spent roughly a decade selling top-down enterprise before deliberately taking a job in a category she knew nothing about. Timestamps: • (00:00) The AI theater • (01:41) Welcome to the Crew podcast • (02:39) Leaving the operator seat for Peak XV • (07:44) What Peak XV is, and her three engagement models • (10:25) The question she gets most in office hours • (11:23) Comcast, Drawbridge, and Lattice from $3M to $100M • (14:17) Two types of go-to-market leaders • (14:38) Top down versus bottom up, and where each one breaks • (18:06) Trap one: hiring AEs before you have demand • (20:27) Trap two: not hiring fast enough at 500% attainment • (22:14) Why she ignores resumes and logos • (24:31) Trap three: the founder who passes the hot potato • (26:27) Centralized or decentralized AI ownership • (29:05) Behind closed doors, none of it is solved • (31:20) How she diligences a company • (34:19) The hypotheticals that expose a founder • (38:08) Why traction alone has eroded as a signal • (38:47) The full body yes • (39:47) Run your own race • (42:22) What she would tell her younger self About The Crew Podcast The Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies.Every week, host Chris Balestras, partner @ Crew, talks to the people actually building go-to-market motions in real time, not in retrospect. About Crew Crew is a recruiting, investing, & media firm for seed through series D AI-natives & fast-growing SaaS startups. This Episode Is Brought To You By Attention: Put a team of revenue agents on every deal. Attention captures every customer interaction without a bot in the room, updates your CRM, automates your reporting, scores reps and opportunities against any framework, and forecasts in a way you can actually trust. Trusted by Lovable, Abridge, Avoca, and hundreds of other fast-growing companies. Try it at https://www.attention.com/ Metaview: The agentic recruiting platform, built for hiring end to end. Metaview's agents source and reach out to candidates in your own tone, review every inbound application against your criteria and tell you exactly why someone made the shortlist, join every call and deliver structured notes the moment it ends, and surface trends across your pipeline from salary expectations to AI fluency. Recruiters, hiring managers and agents all work off one layer of context, with permissions and a full audit trail behind every output. Trusted by Deel, Brex, Deliveroo, Replit and thousands of other teams. Start for free at https://www.metaview.ai/ Where to Find CrewLinkedIn: https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Website: https://www.withcrew.ai/ Blog: https://www.withcrew.blog/ | |||
| Why I Left VC To Get Back Into The GTM Operating Seat w/ Liam Mulcahy, Head of GTM @ Parallel | 08 Sep 2026 | 01:08:55 | |
This week Chris sits down with Liam Mulcahy, Head of Go-to-Market at Parallel Web Systems, who spent seven years in venture at Kleiner Perkins before taking an operating role and bringing seven people with him. Liam's claim is that the innovator's dilemma gap has effectively closed: Parallel has closed roughly 10 Fortune 500 enterprises in the last four months, one of them the fastest AI deal a major bank could remember, and those buyers are now evaluating with the same sophistication as agentic-native companies. He also makes the case that a modern GTM org needs 50% fewer salespeople up to half a billion in revenue, walks through the payback-of-one standard he holds new reps to inside 45 days, and explains what happens when a rep shows up with a PhD-level brief built in Claude and can't say whether the prospect is based in New York or San Francisco. It's his second time on the show, and he spends most of it arguing against the way sales teams are still being built. Discussed In This Episode • Why the innovator's dilemma gap has almost disappeared for companies building on the frontier • The 10 Fortune 500 deals Parallel closed in four months, and the bank that called it their fastest AI deal ever • Payback of one: covering a rep's full base salary in closed deals within 45 days • Why he thinks you need 50% fewer salespeople up until half a billion in revenue • Teaching classically trained sellers to be technical, and technical sellers to run a real process • The Claude brief that looks perfect and still can't tell you how the company makes money • Why "that ignorance is unemployment" if you're not building with these tools for fun • Leaving seven years in VC for an operating role, and the seven people who came with him • Why he wanted founders with perspective, and the Father's Day tea he didn't want to explain to a 24-year-old Timestamps: (0:00) Cold open + intro (3:00) The Paul Graham "GTM is bogus" tweet (4:12) From Kleiner Perkins back to the operator seat (9:57) Getting the band back together: the seven who came over (12:10) Picking your spot in the AI stack (16:02) The eval harness: a fourth party in every deal (23:36) Influencing deals you're boxed out of (27:43) The enterprise lag is dead (33:12) Capacity math: the Degnan debate & payback of one (39:35) Jevons paradox & the one-person-company myth (42:01) When to use AI in sales - and when it backfires (44:26) "How does this company make money?": the Claude doc story (50:51) The new org chart: deployed engineers & the end of the CSM (54:36) Paid extroverts: why founders hire consultants post-sale (56:37) Why Parallel will never hire BDRs (1:01:50) Ignorance is unemployment: every rep needs a GitHub (1:06:45) Where the talent went - and the Shawshank close About The Crew Podcast The Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Crew (a recruiting, investing, & media firm for seed through Series D AI-natives & fast-growing SaaS startups) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today. No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts. About Crew Crew is a recruiting, investing, & media firm for seed through Series D AI-natives & fast-growing SaaS startups. Where to Find CrewLinkedIn: https://www.linkedin.com/company/crewgtmYouTube: https://www.youtube.com/@thecrewgtmNewsletter: https://www.withcrew.blog/Website: https://www.withcrew.ai/ | |||
| Why Utah Produces Elite Sales Talent + Building The GTM Machine @ Exa w/ Marcus Holm, CRO @ Exa | 01 Sep 2026 | 01:03:03 | |
Marcus Holm is the Chief Revenue Officer at Exa, the search API built for agents, now used under the hood by Cursor and Cognition's Devin among others. He joined in 2026 after nearly four years at LaunchDarkly, where he was CRO and then President and took rep quota attainment from 18% to 54%. Before that he led go-to-market at Heptio, the Kubernetes company founded by Craig McLuskie and Joe Beda, and at Cloudera during the Hadoop wars. He spent three and a half years at Cisco across Raleigh, Dallas, Singapore, and the Bay Area. He started out knocking doors on commission in college, and before that spent two years in Latvia and Estonia selling religion to atheists in Russian, a language he did not speak when he arrived. Discussed in This Episode: • Why AI companies keep building their sales teams out of Utah, and what an 18-month church mission does to a person's tolerance for rejection • Why door-to-door is the most intimidating sale there is, and how telesales and field sales each get easier from there • Commission-only math: 25 reps go out for the summer, ten are left by the end of it • The 75% pay cut he took on purpose to leave door-to-door for an SDR seat at Cisco • Two special needs brothers, a sister who died of cancer, a father who went bankrupt, and the risk tolerance that came out of it • "Who will Claude not kill": the durability test he ran on Exa, and why years of sweat equity is the only real moat • Why Exa's human users are now growing faster than its agent users, which was not the founding thesis • The ICE framework, and why he will hire someone with no dev tools experience if the raw materials are there • The management belief he abandoned: that good sellers have to be wired like him • How LaunchDarkly went from 18% to 54% of reps over plan, and why "70 at 70" no longer holds in AI • Quota attainment benchmarks now: 30 to 40% is the norm, over 50% is best in class Timestamps: • (02:18) Welcome, and why Exa's investors kept texting Chris about Marcus • (03:30) Why AI companies keep building sales teams in Utah • (05:33) Why door-to-door is the most intimidating sale there is • (06:31) His father the sales trainer, Super Target, and the date that needed a car • (09:39) Commission only: 25 reps in June, ten by August • (12:38) The adversity that set his risk tolerance • (16:15) How he ended up a technical seller, and the superpower he found learning Russian • (19:09) Seattle, Heptio, and the orchestration wars • (21:34) Learn, earn, grow: how to pick your next company • (24:56) Channeling his inner VC on Exa • (28:27) Who Claude won't kill, and why the open source graveyard is the analog • (34:54) Websites vs. the API, and humans becoming the customer • (40:15) Signals, propensity data, and giving developers free consulting • (43:56) The ICE framework for hiring • (46:11) What he changed his mind about in hiring • (48:17) The AI tools his reps actually use • (51:55) From 18% to 54% quota attainment • (58:38) Forward deployed engineers and doing more with fewer people • (1:02:04) GTM mafias, and why the AI era is too early to call About The Crew Podcast The Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Crew, talks to the people actually building go-to-market motions in real time, not in retrospect. About Crew Crew is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups. Where to Find Crew LinkedIn: https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Website: https://www.withcrew.ai/ Blog: https://www.withcrew.blog/ | |||
| Why Remote Breaks at Scale & the GTM Playbook Behind AI Agents w/ Darren Moffett, VP of Sales @ LangChain | 25 Aug 2026 | 00:56:36 | |
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 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 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/ | |||
| Inside the GTM Playbooks at Twilio & Vanta w/ Stevie Case, CRO @ Vanta | 18 Aug 2026 | 01:02:03 | |
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 About The Crew Podcast 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 Where to Find Crew LinkedIn: https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Newsletter: https://www.withcrew.blog/ | |||
| The First Sales Hire Mistake That Sinks Startups w/ Rafa Jara-Simkin, Partner @ Theory Ventures | 11 Aug 2026 | 00:56:06 | |
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 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/ | |||
| 12 Things That Top Candidates Are Doing To Land Offers in 2026 w/ Chris Balestras, Co-founder @ Crew | 06 Aug 2026 | 00:54:03 | |
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 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 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/ | |||
| How We're Scaling Vercel's GTM Motion Through A 9B Valuation w/ Nick Bogaty, CRO @ Vercel | 04 Aug 2026 | 00:48:49 | |
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
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 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/ | |||
| How Clay Built the GTM Team Behind a $5B Valuation w/ Becca Lindquist, Head of Sales @ Clay | 28 Jul 2026 | 01:01:19 | |
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:
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 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 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/ | |||
| Why Product Love Doesn't Actually Close Deals w/ Simran Duggal, VP of Sales @ Juicebox | 21 Jul 2026 | 00:52:36 | |
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:
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/ | |||
| Don't Take the Anthropic Job First w/ Mark Goldberger, VP Sales @ Metaview | 14 Jul 2026 | 00:58:22 | |
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:
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 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/ | |||
| How To Pick The Right AI Company To Bet On & Operationalize Champion Building w/ Bryan Cox, VP of Worldwide Sales @ Braintrust | 07 Jul 2026 | 00:52:36 | |
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. | |||
| State of GTM Recruiting @ The AI-Natives w/ Chris Balestras, Co-founder @ Crew | 04 Jul 2026 | 00:26:44 | |
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
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. | |||
| Sales Mafias & What Made MongoDB Great w/ Graham Moreno, VP Worldwide GTM @ Parallel | 30 Jun 2026 | 00:58:11 | |
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 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 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. | |||
| How We're Building Granola Into the Most Beloved Product in AI w/ Bardia Shahali, VP Sales @ Granola | 23 Jun 2026 | 01:01:47 | |
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 About The Crew Podcast 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 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 | |||
| How To Hire Sales Reps Like a Moneyball GM W/ Navid Zolfaghari, Chief Sales Officer @ Zapier | 16 Jun 2026 | 00:56:10 | |
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 | |||
| How The Best Salespeople Are Building Agents in GTM w/ Roy Mathew, Head of Sales @ Gumloop | 09 Jun 2026 | 01:00:35 | |
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 | |||
| Every Startup Is Lying to You, So Here's How to Pick the Right One w/ Glenn Rachlin | 02 Jun 2026 | 00:57:24 | |
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 | |||
| How Harvey Scaled GTM to an 11B Valuation w/ Rob Saliterman, VP of Sales @ Harvey | 26 May 2026 | 00:49:26 | |
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
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/ | |||
| Why The Best Sales Rep You Interview Is Probably Your Worst Hire with Mike Heller, Partner @ Floodgate | 19 May 2026 | 00:51:16 | |
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
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/ | |||
| How We Built Profound’s GTM Motion To A $1B+ Valuation w/ Mark Ebert, SVP of Revenue @ Profound | 12 May 2026 | 00:44:10 | |
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
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/ | |||
| Why "AI for Finance" Is Meaningless & Why Bankers Make the Best Sellers W/ James White @ Rogo | 05 May 2026 | 00:46:44 | |
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:
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/ | |||
| The Old Sales Playbook Is Dead: Hiring + Selling In The AI Era w/ Jacquelyn Goldberg, VP Sales @ Unframe AI | 28 Apr 2026 | 00:55:49 | |
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/ | |||
| Tell Them the Movie Before They Watch It: Enterprise Sales, Champion Building & the No-Pilot Stance W/ Adam Ali, SVP Revenue @ Rox | 21 Apr 2026 | 00:57:48 | |
Adam Ali's Background Adam Ali is the SVP of Worldwide Revenue at Rox, an AI-native revenue operating system backed by Sequoia, GV, and General Catalyst. He joined in September 2025 after being named Glean's Top Sales Leader of 2025 and leading the entire company in total revenue growth, net new enterprise logos, and time to productivity per rep. Before Glean, Adam spent six years at Rubrik, joining when the company was at $20M ARR and helping scale to over $700M ARR. Before that, he got in his early reps at SAP, where he was #1 in the sales academy every week. Unlike most people in sales, Adam didn't fall into it. He started the sales program at the University of Arizona before graduating and was prospecting his way into jobs as a student. Discussed In This Episode
Timestamps (00:00) Intro & Adam's Background (02:08) Being Sales-Pilled Before Graduation: Starting the Sales Program at U of A (06:02) Landing at SAP & What Big Company Sales Actually Teaches You (07:33) Executive Presence Training: Stillness, Eye Contact & Body Language (09:58) The Manager Who Left for Rubrik & Planting the Seed (14:40) The $100 Bill Story: Human Capital & Getting in the Game (18:56) Champion Building: Test First, Build Second (22:01) The Difference Between a Champion and a Coach (23:35) Shadow Selling: What Happens Between the Meetings (25:53) How to Test Whether Someone Is Actually Your Champion (29:14) The No-Pilot Stance: EB Go/No-Go and Proof of Value (36:17) Tell Them the Movie Before They Watch It (38:37) How to Build Momentum Inside a Single Meeting (41:04) Breaking the Deal: How to Find Out What's Really Going On (45:33) Rox, AI Sales Tech & Where the Landscape Is Heading (51:57) What an Agent Swarm Actually Means (57:35) Why Adam Made Two Bets on AI Companies (1:00:35) How to Get Hired at Rox 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/ | |||
| Fewer Reps, More Pipeline: How AI-Native GTM Teams Are Doing More With Less w/ Jason Miller, VP Sales @ Unify | 14 Apr 2026 | 00:51:46 | |
Jason Miller is the VP of Sales at Unify, a signal-based selling platform helping go-to-market teams connect buyer intent to personalized outreach at scale. Before Unify, Jason spent just over seven years at Monday.com, joining as one of the first 12 US sales hires when the company was almost entirely PLG and didn't even believe it needed a sales team. He helped build the outbound motion from the ground up, moved into sales leadership, and scaled the company through hypergrowth to IPO. Prior to Monday.com, Jason was at Convey (now project44), where he took over the founder-led sales playbook and built out the SDR and AE teams in the scrappiest of environments where you either learn fast or you don't last. He came up reading Predictable Revenue, built his career on the belief that inputs always drive outputs, and carries a clear philosophy into every org he joins: hire slow, keep the bar high, and don't confuse quota attainment with talent. Timestamps (00:00) Cold open: the Mount Rushmore of GTM signals(02:28) Jason's background: falling into sales and finding SaaS(05:30) What makes the Israeli tech scene different from SF and New York(09:35) Crossing the PLG chasm: why he left Monday for a sales-led company(10:19) Why he almost didn't join a go-to-market company (and what changed)(12:07) How to evaluate founders in an interview process(14:14) The dating analogy: finding the right sales culture fit(14:50) The hiring mistake that taught him never to lower the bar(16:52) How to prevent "shiny object" bias in an interview loop(18:56) What top candidates actually do differently (the follow-up problem)(20:24) Asking better questions: layers, active listening, and interview-as-discovery(22:23) The $1M growth hire and the future of the sales team(25:52) The sales tech landscape in 2026: how to cut through the noise(29:04) Ideal stack for a Series B AI-native: CRM, CI, sequencer, signals(30:53) Clay vs. Unify: how to think about using both(33:24) PLG vs. SLG: what really changes when the inbound stops(38:17) The three metrics every AE should track(39:46) Why quota attainment can be misleading(45:13) Cold outbound isn't dead (it just has to be better)(47:45) Roleplay, reps, and why HyperBound might be the most underrated tool(50:05) Methodologies that actually matter: MEDIC, MEDDPICC, Spiced 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/ | |||
| How to Reinvent Yourself & The Athlete Mindset Behind Elite Sales Teams w/ Evan Cassidy @ Decagon | 07 Apr 2026 | 00:58:52 | |
Evan Cassidy’s Background Evan Cassidy is the VP of Sales at Decagon, the leading AI-native customer support platform. He joined as the company's first sales hire when it was doing less than $2M in ARR. Now? Decagon is valued at $4.5B, and Evan has been instrumental to scaling the GTM org along the way from a team of ten through Series A, B, C, and D. Before Decagon, Evan held sales leadership roles at Drift and Dropbox (after getting rejected the first time and doing a 10-month stint at Yelp to build his foundation) before reapplying and landing the role. Before getting into tech, Evan was a competitive rower: captain of Columbia's heavyweight team, two-time US Under-23 National Team member, and spent time at the Olympic Training Center in Oklahoma City. Evan had an unconventional start to his career after not starting full-time work until 25 that included driving across the country to San Francisco with no job, no plan, and not much money. His career has been a study in reinvention and in knowing when to throw yourself in the deep end. Timestamps (00:00) Intro & Evan's story: from rowing to Oklahoma City to San Francisco (06:16) Columbia's 100-year rebuild in 2 years and how that shapes Evan’s approach to team building today (11:22) What traits replace "former athlete" for candidates who didn't play college sports (15:17) Breaking into tech in 2013 and why Dropbox was the target (20:06) Getting rejected, going to Yelp, and coming back to get the job 10 months later (25:12) Why most people ruin their job search by skipping the inner work (28:45) The Never Search Alone approach and the feedback that redirected his career (33:00) What "feeling stuck" actually feels like and how one moment with an exec coach shifted things completely (40:50) Joining Decagon with a 2- and 3-year-old and under $2M in revenue (46:11) The AI bifurcation and why salespeople need to move now (51:37) What Decagon's GTM culture looks like and who is actually a good cultural fit (57:15) Building a magnetic organization: what it means, why it matters(01:01:30) Where customer support automation goes from here 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/ | |||
| The $1M Salary GTM Role Nobody Qualifies For Yet w/ Jason Gelman, GTM Partner @ Primary VC | 31 Mar 2026 | 01:04:02 | |
Jason Gelman’s Background Jason Gelman is a Go-to-Market Operating Partner at Primary Venture Partners, one of the largest early-stage VC firm that just closed its $625 million Fund V (the largest to date) a few days ago, bringing total AUM to ~$1.6B. Before Primary, Jason led Revenue Strategy & Operations at Compass, helping scale the company from ~$100M ARR to $6B through their IPO. He got his start in the New York tech scene after attending law school, where he quickly realized the meritocracy of tech was a better fit for him than the rigid hierarchies of the legal world. He’s never looked back. At Primary, Jason has built out two core programs for portfolio companies: a Market Development team (centralized BD outreach on behalf of founders) and a Go-to-Market Engineering program (tech stack buildout and systems architecture). He's also leading the development of the firm's investment thesis around go-to-market tech. Discussed In This Episode • How Primary's portfolio support model actually works and why "advice-giving" doesn’t cut it • The Market Dev team's unfair advantage: why outreach from Primary converts better than any vendor pitch • The Go-to-Market Architect role: why it's different from a GTM Engineer (and why Clay's definition falls short) • Why a profile with deep experience in legacy SaaS tools + fluency in modern AI will easily earn $500K to $1M+/year •How to find the rare 3-in-30: RevOps chops + AI fluency + business acumen • The Full Stack GTM person: one role replacing marketer + SDR + AE • How the PNL test should filter every sales tech investment and why the old "time savings" ROI story is dead • Where Salesforce is headed in the next 10 years and why its pricing leverage is finally at risk • Why Slack might be Salesforce's best asset going forward • Small teams doing massive revenue: what $1M+ IRR per employee actually looks like • How to break into VC from a go-to-market background Timestamps (00:00) Intro & Jason's Background: From Law School to NYC Tech (07:15) The Go-to-Market Operating Partner Role: What It Is (and Isn't) (11:38) How Primary's Portfolio Support Programs Were Built (16:42) The Market Development Team: Primary's Unfair BD Advantage (21:26) Go-to-Market Engineering: Building the Stack for Founders (25:43) The GTM Architect vs. GTM Engineer and Why the Distinction Matters (30:09) Why This Profile Will Earn $500K–$1M+ and How to Find One (34:21) The Full Stack GTM Role: One Person Replacing Three (37:07) Primary's Investment Thesis: The PNL Test for Sales Tech (42:30) Where Salesforce Is Headed and Why Its Grip Is Finally Slipping (49:04) Small Teams, Massive Revenue: GTM Efficiency Benchmarks (55:35) How to Break Into VC from a Sales/GTM Background 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/ | |||
| How The Best CROs Actually Hire Salespeople w/ Kyle Norton, CRO @ Owner.com | 24 Mar 2026 | 01:07:44 | |
Kyle Norton is the CRO of Owner.com, the all-in-one online presence platform for independent restaurants: think Shopify Plus meets HubSpot, but built specifically for your neighborhood restaurant that’s your go-to for ordering in on a Thursday night. He's taken Owner from $2.5M ARR to $100M in just under four years, with 2025 growth outpacing 2024. Before Owner, Kyle spent three years at Shopify where he built out the Point of Sale go-to-market organization and then ran the Canadian market, which is a quarter-billion-dollar business. Prior to Shopify, he was the first-time VP of Sales at League, taking them from 0 to $25M ARR. Kyle started his career in sales in 2008 during the financial crisis (tough timing that forged a great seller) and has been building and rebuilding revenue teams ever since. He was only an individual contributor for 14 months total before moving into leadership, which speaks volumes. Kyle recently relocated from Toronto to San Francisco, and he'll be the first to tell you the dinner conversations there are on another level. He works basically nonstop, thinks deeply about first principles, and has a well-known polarizing style: intense, hyper-transparent, and deeply opinionated about language and systems. Discussed In This Episode • Why case study scores have almost no correlation with rep performance • The halo effect in hiring: how charisma hijacks your scorecard and what to do instead • Why "organized operators" consistently outperform charismatic closers at Owner • The barbell happening in both companies and talent and what it means for your career right now • Why a VP of Sales title at a mediocre company is a worse bet than first-line manager at a world-class one • How to do real diligence on a company before joining: who to talk to, what to ask, how to find the dirt • Why Kyle brings in Rev Ops and Enablement earlier than almost anyone and the exact 80/20 moves to start with • Centralized vs. decentralized AI strategy and why Owner chose to keep it centralized • The AI tools giving Owner a real edge: Avira for rep training, Triggers for post-sales, OneMind for AI-native selling • How Kyle uses Claude Code as a personal chief of staff, from performance reviews, to weekly updates, and more Timestamps (00:00) Intro & Kyle's Move from Toronto to SF (04:00) Starting a Career in Sales During the 2008 Financial Crisis (10:00) League, Shopify, and the Path to Owner.com (16:00) What Owner.com Actually Does (and Why Their Model Works) (22:00) Joining Owner: Talent Assessment, Radical Transparency, and Mutual References (30:00) Why Case Studies Are Broken (Sort Of) (38:00) The Halo Effect, Scorecard Hiring, and Why Operators Win (44:00) The Barbell: Companies, Talent, and Career Selection in 2025 (52:00) How to Actually Diligence a Company Before You Join (58:00) Hire Rev Ops & Enablement Earlier Than You Think (01:04:00) Centralized AI Strategy: How Owner Builds, Deploys, and Adopts AI Tools (01:12:00) Kyle's Personal AI Stack: Claude Code, Open Claude, and Building Your Own Chief of Staff 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 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/ | |||
| My #1 Rep Closed $3.5M & Never Sold A Day In Their Life w/ Ghazi Masood, CRO @ Replit | 17 Mar 2026 | 00:49:15 | |
Ghazi’s Background Ghazi Masood is the CRO at Replit, one of the most talked-about companies in the AI era, building what they consider to be the only credible end-to-end vibe coding solution for enterprises. Before Replit, Ghazi was VP of Sales at Retool, where he helped scale one of the most elite GTM teams in developer tooling. Before that, he spent 4+ years at Auth0, joining early and leading all aspects of revenue growth for the Americas - scaling from $28M to $300M+ in 4 years before Okta acquired Auth0 for $6.5B in 2021. Ghazi is one of the most respected GTM leaders in the developer tooling and technical products space - it was fun to dive into his philosophy on hiring nontraditional sellers, why most companies staff for aspiration instead of demand, and how the AI era is fundamentally changing the way enterprise sales orgs are built. Discussed In This Episode • Why Replit's #1 seller closed $3.5M and had never sold a day in his life and what that actually means for how AI companies should hire • The "panel presentation" interview format and why Ghazi makes every candidate show what they've built in Replit before they get the job • Staff demand, not aspiration and the back of the napkin math every sales leader needs to do before hiring their first rep • Why Ghazi renamed his SEs to "Field Engineers" and rewrote the traditional pre/post-sales model • The work hard, play hard culture that made Auth0 special and how he's rebuilding it at Replit • Back channeling done right and why he never calls the references candidates give him • Why tenure is the most underrated signal in a sales resume right now • The founders' mistake he sees over and over: hiring a VP of Sales too early • How Replit is using its own product internally from CPQ tools to SDR call scripts • Why distribution is the new moat (not technology) and what that means for how you build a GTM org in 2025 Timestamps (00:00) Intro, What Replit Is Building & Why Ghazi Joined (04:00) Building the Auth0 Culture: Work Hard, Play Hard & The Off-Sites That Actually Mattered (12:00) From Auth0 to Retool: What Great GTM Culture Actually Looks Like (18:00) Why Replit's Best Reps Have Never Sold Anything and How Ghazi Finds Them (26:00) The Panel Presentation: Ghazi's Highest-Signal Interview Step (32:00) How AI Is Changing the Sales Org Structure and Why Field Engineers are Replacing SEs (38:00) Staff Demand, Not Aspiration: The Back of The Napkin Math Every Founder Needs to Do (44:00) What to Ask in a VP of Sales Interview to Know If the Pipeline Is Real (50:00) Back Channeling, Tenure & How Ghazi Actually Evaluates Candidates (56:00) Hiring Senior Sales Leaders Too Early, Distribution Is the Moat & The Advice He Keeps Giving Founders Who Won't Listen 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/ | |||
| Why Anthropic is The Hottest Company in AI & & How To Use Claude As A Seller w/ Eleanor Dorfman, Head of Industries @ Anthropic | 10 Mar 2026 | 00:56:43 | |
Eleanor Dorfman is the Head of Industries at Anthropic, where she leads enterprise go-to-market for Claude at the epicenter of the AI revolution. Before Anthropic, Eleanor built and scaled GTM teams at some of the most talent-dense companies of the last decade. She started her career at Clever (where she turned multiple rejections into an eventual yes through sheer conviction and follow-through), moved to Segment, where she transitioned from customer success into sales and built the expansion motion, and then joined Retool as an early sales leader, helping scale the org through hypergrowth. She also advises early-stage companies and has worked closely with venture firms like Thrive Capital giving her a front-row seat to how breakout startups are built and how early GTM hires play a mission-critical role in either accelerating or stalling that trajectory. From public education to developer tooling to AI labs, Eleanor’s career looks less like the traditional “ladder” and more like what she aptly describes as a “jungle gym.” Discussed In This Episode • Why careers are a jungle gym, not a ladder and how to pivot on “one foot”• Getting rejected (and rejected again) and why persistence + conviction still win• The moment she realized sales was about energy, not personality • What makes a seller truly AI-native and how top reps are using Claude today • How to use Claude Code to build live prototypes (and why you may no longer need your sales engineer) • Why “not technical enough” is often a lazy hiring critique • The curiosity test: the one interview question that flipped her from “no” to “yes” • Why early startup hires require a founder mentality • The “ego death” principle and how ego hinders hypergrowth • Why she doesn’t care about “productive capacity” in the AI era • Learning vs. earning vs. values and the difference between Anthropic vs. other AI-natives • Why Anthropic is enterprise-first and what that means for sellers Timestamps (00:00) From paralegal to public education to startup life (05:10) Rejected three times by Clever and why she kept coming back (11:30) Transitioning from customer success into sales at Segment (16:45) Building the expansion sales motion and falling in love with sales (24:46) Retool, hypergrowth, and scaling GTM in developer tooling (29:30) How to break into an AI lab (and what actually gets a recruiter’s attention) (32:09) Ego death, ownership, and what real commitment looks like (39:00) The myth of “not technical enough” in early GTM hiring (42:43) Claude’s personality: designed, not accidental (44:30) How top reps use Claude Code to build live demos mid-cycle (45:11) Managing in the AI era: throw out productive capacity, optimize for learning (52:24) Why Join Anthropic (58:26) Learning, earning, values and how to play for “the front of the jersey” 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/ | |||
| 11 Traits That Make A Hot Sales Job & How To Avoid Joining A Dud | 03 Mar 2026 | 00:23:15 | |
This week, Chris goes solo. No guest necessary as he breaks down the answer to the question he’s gotten asked more times than he can count: how do I actually choose the right sales job? Chris has spent several years navigating this himself, written articles on it, and interviewed enough VPs of Sales and CROs to know what separates career-defining moves from ones that stall your career trajectory without you even realizing it. The result? His 11 traits framework, which is a crystal clearest distillation of what makes a sales role genuinely great. Discussed In This Episode • The #1 thing the happiest, most successful people in Chris's network all have in common, and why most people make the mistake of not prioritizing it • GTM mafias and talent vortexes: why 90% of the time, the people landing the best jobs have a champion on the inside • Why OpenAI and Anthropic are career insurance, and what that snowball effect actually looks like in action • The "breakout period" of the Series A through C sweet spot that startup veterans optimize for, and why the AI natives have blown up the old ARR benchmarks • The inbound tailwind test: if more than 30% of deals are outbound, what that signals about the environment you're walking into • Why some of Chris's friends joined PLG companies with tons of inbound but still hated the job • The path-to-enterprise question every seller needs to ask before signing an offer, and why $100K deal size is the minimum bar he'd set • Selling complex products vs. app layer and why Chris wishes he'd gone more technical earlier • What "AI native" sales leadership actually looks like vs. the dinosaur playbook • Why in-person matters in the AI era, and the Keith Rabois framing that explains the feedback loop advantage • How to do due diligence on engineering shipping velocity before you join, and why it directly affects your close rate as an AE • Back channeling the right way: who to actually talk to, why VCs don't know what you need to know, and why Repview has its limits Timestamps (00:00) Why Chris Is Going Solo For This Episode (02:22) Trait #1: Join a Mafia or a Talent Vortex (04:45) Trait #2: Clear Signs of Market Pull Via the Inbound Tailwind Test (06:15) Trait #3: The Breakout Period Explained: Find the Risk-Reward Sweet Spot (08:00) Trait #4: Does the Product Have a Path to Enterprise? The $100K Deal Question (10:30) Trait #5: Why Actual Interest in the Industry and Problem is a Prerequisite to Sell Well (11:30) Trait #6: Why Technical Sales Compounds Your Career (13:30) Trait #7: The Ability to Do More Than Just Sell at an Early-Stage Startup (15:00) Trait #8: Sales Leadership Must Be AI Native (and What That Actually Means) (17:30) Trait #9: New York and/or SF Presence and the Case for the In-Person Feedback Loop (19:45) Trait #10: The Engineering Team Needs to Be Shipping Constantly and How to Test Them (21:30) Trait #11: Back Channel Everything: Who to Talk To and Who to Skip (23:30) Recap of All 11 Traits & What's Coming Next on Vibescaling 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/ | |||
| The Art & Science Of Choosing Which Startup To Join & How To Value Your Equity w/ Billy Gallagher, CEO @ Prospect | 24 Feb 2026 | 00:55:14 | |
Billy’s Background Billy Gallagher is the founder and CEO of Prospect, a robo-advisor that helps startup employees better manage their private company equity. Think: Wealthfront for startups. Before Prospect, Billy was on the investing team at Khosla Ventures, where he worked on early-stage deals from seed through Series B, including companies like Stripe, DoorDash, and Instacart. He then joined Rippling as the 34th employee in a generalist "special projects" role, staying for three and a half years as the company scaled to over a thousand people. Between Khosla, Rippling, a Stanford MBA, and a stint covering startups at TechCrunch, he's seen the startup equity problem from literally every seat at the table The gap he kept seeing between how professional investors managed equity at Khosla vs. how employees fumbled through it at Rippling is exactly what led him to start Prospect. Timestamps (00:00) Intro & Billy's path from Khosla Ventures to Rippling to founding Prospect (03:44) How to evaluate a startup quantitatively: investors, headcount, web traffic (05:14) Why the lead investor's seniority level matters more than the firm name (07:14) Tracking investor quality across rounds (and when it's a red flag) (09:17) The rise of the solo GP and what it signals for employees (10:18) Second-time founders vs. first-time founders: when experience is an edge (12:10) The Ramp example: hitting a double, staying hungry, then hitting a grand slam (13:27) Tools for researching startups: Prospect, Crunchbase, and what to look for (17:30) Headcount growth as a proxy for business growth (19:54) Secondary market signals: what they tell you about a company between rounds (22:14) When a fundraising gap is a red flag vs. a sign of capital efficiency (24:46) The breakout period: why Series A–C is the best risk-adjusted time to join (30:23) Qualitative signals: founder vision, speed, and the talent vortex (32:07) How to spot a fast-moving founder without asking a single question (34:00) Talking to customers: developing taste for product-market fit (36:42) Market timing and the Paul Graham test: it should feel almost too late (39:53) Equity 101: options vs. RSUs and when you'll get each (41:50) QSBS and early exercise: the tax advantages most employees miss (43:59) Post-termination exercise windows: why 90 days is no longer acceptable (47:38) Percent ownership: how to benchmark your equity offer (49:23)Tender offers and the 20% rule: taking chips off the table without losing upside (52:24) What Prospect does and how to use it to navigate your equity lifecycle 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/ | |||
| The Best Sales Reps Are Coin Operated & All Roads Lead Back To The Steak Dinner w/ Jack Gashi, VP of Sales @ Avoca | 17 Feb 2026 | 01:05:28 | |
Jack's Background Jack Gashi is VP of Sales at Avoca, an AI-native platform bringing automation to home service businesses. At Avoca, Jack is building the sales organization from scratch as the company scales AI-driven voice and scheduling technology across industries. Before Avoca, Jack spent several years at Check, a high-growth cybersecurity startup, where he learned what it actually takes to build durable GTM teams. Prior to that, he worked in ad sales at Foursquare during the company’s peak growth years, and even earlier in his career Jack cut his teeth in classic boiler-room sales at Yext, making hundreds of cold calls a day selling into home services. Through experience across SMB, mid-market, and enterprise sales, Jack knows what it actually takes to build a sales org that works. His philosophy is rep-first and unapologetic: sales is coin-operated, built on trust, and keeps the lights on. He’s a proud Jersey guy, a former Fyre Festival attendee (yes, really), and the first to admit that the best sales conversations still happen face-to-face. Discussed In This Episode • Why fear-based sales cultures break down while trust-first cultures actually scale • Jack’s early career in boiler-room sales (150 cold calls a day) and why that foundation still matters • How tech sales talent evolved from “falling into it” to Ivy League grads choosing it deliberately • The “trough of disillusionment” every sales career hits • Why sales is coin-operated and why pretending money doesn’t matter creates misalignment • The hidden, spreadsheet-level cost of losing a $2M ARR top rep • How to spot whether sales is a first-class citizen or a “necessary evil” at a company • Why PLG works… until it doesn’t • How real trust gets built (hint: it’s not five-step cadences) • Why great AEs sell their own job search like a deal • What sales skills transfer to real life Timestamps (00:00) Why fear-driven sales cultures fail — and what actually builds trust (03:29) Fyre Festival and the danger of believing the outside story (06:03) 150 cold calls a day at Yext and learning to really sell (09:28) How tech sales talent has changed — Ivy League grads choosing sales (15:03) The “trough of disillusionment” in a sales career (18:19) Stop romanticizing work (21:26) Sales morale as the beating heart of a company (23:09) How to tell if a founder truly respects sales (25:03) The real cost of losing a top rep (26:11) “All roads lead back to steak dinners” — the limits of PLG (29:00) Sales as trust transfer, not scripts (31:02) Why automation and perfect sequencing keep failing (33:04) Product knowledge as a trust weapon (36:31) When to leave a good job — why Jack chose Avoca (44:15) How elite AEs evaluate roles when data doesn’t exist (46:06) Are the best reps coin-operated? (53:41) What’s dead in modern sales 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 Company Page - https://www.linkedin.com/company/vibescaling/ YouTube - https://www.youtube.com/@vibescaling Newsletter - Website - | |||
| The Words You Use Are Killing Your Trust & What Great Sellers Do Instead W/ Sam Berg, VP of Sales @ Tennr” | 10 Feb 2026 | 01:06:13 | |
Sam’s BackgroundSam Berg is the VP of Sales at Tennr, one of the fastest-growing companies in the healthcare AI space. Sam leads Tennr’s sales org during a period of hyper-growth, where he’s laser-focused on building disciplined sales teams while scaling a high-trust sales motion. Before Tennr, Sam spent nearly 8 years at VTS (formerly Hightower), where he rose from individual contributor to sales leader, helping to scale an enterprise sales org selling into commercial real estate brokers. Like many other great sales leaders, his career had a seemingly innocuous start: selling tickets to New York Islanders games and building a customer-first sales approach in the process. Sam builds sales teams and systems that scale by earning trust, not burning it. Discussed In This Episode • From $8/hour ticket sales to VP of Sales - how early habits compound • Why discipline and curiosity matter more than talent (and how he actually tests for them in interviews) • His sales interview philosophy: preparation > polish • The competency framework he built to promote SDRs into enterprise reps • Why great sellers sound calm by using trust signals• Transparency breaks patterns - how setting negotiation guardrails builds trust • Why he avoids words like “deal” and “feedback” and how language subtly shapes buyer behavior • How to find the real urgency that accelerates enterprise deals • Why creating context beats jumping to discovery • Why competition fuels the best sales teams pushing to out-execute each other Timestamps (00:00) Intro, Brooklyn vs. Long Island debate & why food opinions matter more than sales titles (05:00) From club promoting to ticket sales: getting paid $8/hour and taking “small” sales seriously (10:00) Early account research hacks & learning willingness-to-pay the hard way (16:00) “I don’t want to sell glass seats. I want to buy them”: deciding to leave sports for software (21:00) Breaking into software sales, early career mistakes & choosing the small pond over the big logo (27:00) Selling outcomes vs. features: the inflection point that changed how he sold forever (33:00) Transparency as a sales weapon: naming weaknesses, breaking patterns & earning trust (39:00) Internal vs. external change: what actually creates urgency in enterprise sales (45:00) From Hightower to Tennr: why vertical, “unsexy” industries are the best place to sell (50:00) Joining Tennr early: hypergrowth energy, imposter syndrome & “Hamilton-level” intensity (55:00) Building a sales team from scratch: why discipline and curiosity beat raw talent (01:01:00) How he interviews sellers: testing preparation, hypotheses & real curiosity (01:07:00) Tone, cadence, and posture: why great sellers sound calm instead of clever (01:12:00) Words that kill trust (“deal,” “feedback”) and what to say instead (01:17:00) Healthy sales competition: winning on execution, not hoping teammates fail 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 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: YouTube: Newsletter: Chris from vibescalingHome | Vibescaling Blog Website: | |||
| Why You Should Join Cursor Over OpenAI and Anthropic & How To Avoid Bad Sales Hires W/ Tomer Chernia, VP of GTM @ Cursor | 03 Feb 2026 | 00:57:53 | |
Tomer Chernia is the VP of GTM at Cursor, one of the fastest-growing companies in tech - reportedly going from 0 to $500M+ ARR faster than almost any company in history. Before Cursor, Tomer spent three years at Vercel where he helped build out the go-to-market motion and developed their GTM efficiency framework. Prior to that, he was at Branch and Segment as early GTM hires. Tomer got his start in tech at Yahoo, then joined Wildfire pre-acquisition by Google - where he caught the startup bug. He even tried his hand at founding a company before going back to sales. He's a serious foodie (ask him for SF restaurant recs) and recently got into natural wine. Discussed In This Episode • His interview process evolution: from "pitch your product" to discovery sessions + deal reviews • The "three hows" technique for testing candidate depth until their understanding breaks • How Cursor went from 8 GTM people to nearly 100 in six months • Why he chose Cursor over staying at Vercel (the "would you regret it?" test) • The Cursor vs. OpenAI/Anthropic pitch for candidates - why "born adult" matters • Why Cursor pays commissions when others don't - the real tradeoffs • PLG sellers vs. top-down sellers - different strengths, different failure modes • Why sales morale matters more than most leaders admit - and how quota setting destroys it • "Buyers are liars" - why your champion isn't always a reliable narrator • The future of outbound: signal-based, not spray-and-pray Timestamps (00:00) Intro & SF Restaurant Recommendations from a Serious Foodie (04:00) From Humanities Major to Yahoo: How Tomer Fell Into Sales by Accident (12:00) Wildfire, Google, Founding a Company & Why He Went Back to Sales (20:00) The Tap on the Shoulder from Cursor: "Would You Regret Saying No?" (26:00) How to Actually Hire Great Salespeople: Discovery Sessions + Deal Reviews (32:00) The "Three Hows" - Testing Candidate Depth Until Understanding Breaks (38:00) Why Sales Morale Matters: Quota Setting & Rep Motivation (44:00) Cursor's GTM Growth: From 8 People to Nearly 100 in Six Months (50:00) Why Cursor Over OpenAI or Anthropic: The "Born Adult" Company (56:00) The Future of Outbound & How to Stand Out as a Candidate 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 Company Page - https://www.linkedin.com/company/vibescaling/ YouTube - https://www.youtube.com/@vibescaling Newsletter - Website - | |||
| Jack Dorsey Hired Me from My Dorm Room As Employee 100 @ Square | Mike Donahue, CRO @ Maven AGI | 28 Jan 2026 | 01:01:28 | |
Episode Description: Mike Donohue is the CRO at Maven AGI, one of the fastest-growing AI agent companies focused on customer support automation. Before Maven, Mike was SVP of Sales at Gubshup, a messaging AI tool, and spent time at PayPal to give BigCo a spin. He was an early sales hire at Lean Plum, growing with the company from Series A through Series D and competing head-to-head with Braze during the mobile marketing wars. Mike's career started unconventionally - while captain of the varsity heavyweight rowing team at Columbia, he ran a dorm business doing room cleaning, dry cleaning, and beverage delivery. He started using Square to process payments, fell in love with the product, and eventually got hired directly by Jack Dorsey when the company was sub-100 employees. He's a Philly native who will tell you Tony Luke's beats Pat & Geno's as the best cheesesteak in Philly. Discussed in this episode:
Episode Timestamps: (00:00) Intro & Best Philly Cheesesteak: Why Tony Luke's Beats Pat & Geno's (04:00) Running a Dorm Business at Columbia & Discovering Square (08:00) Getting Hired by Jack Dorsey When Square Was Sub-100 Employees (12:00) The Athlete Mentality in Sales: "Score Takes Care of Itself" (18:00) Why Sales is a Science, Not an Art - Playbooks Beat Artists (24:00) How to Evaluate AI Usage in Sales Interviews: Meh, Good & Great Answers (30:00) "I Vibe Coded 80% of My Outbound in Windsurf" - What Impresses Hiring Managers (38:00) Where AI Agents Are Actually Working in Customer Support (45:00) The Braze vs Lean Plum Horse Race: Competing from Series A to C (52:00) Why Sales Dinners Are Dead & Education-First Selling is Winning (58:00) Maven AGI is Hiring - What Mike Looks For in Candidates 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 & SaaS startups) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today. No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts. About Vibescaling: Vibescaling is an advisory, recruiting, media, & investing firm for seed through series C AI-natives & fast-growing SaaS startups scaling from 0 to $100M ARR. Where to Find VibeScaling: | |||
| How I Built Legora's GTM Motion To A $1B+ Valuation w/ Patrick Forquer, SVP Global Revenue @ Legora | 22 Jan 2026 | 01:02:17 | |
Episode Description: Patrick Forquer is the SVP of Global Revenue at Legora, one of the leading players in the AI-native legal tech space, coming off a recent Series C raise to value the company at over a billion dollars. Before Legora, Patrick spent 7 years at Braze (formerly AppBoy) from the early days through IPO, leaving as the AVP of sales. He started his career as a BDR at Yext during the 2008 financial crisis, worked at Intralinks, then moved to Cloud Sherpas, managing their Google Cloud relationship before the Accenture acquisition. He was also CRO at Jacquard, an early generative AI company. Pat is one of the more down-to-earth people I've met in the space; I really enjoyed the conversation + hope you do too. Discussed in this episode:
Episode Timestamps: (00:00) Intro & Pat's Background (02:30) Meeting His Wife at Memory Motel in Montauk (04:30) His Path: From BDR at Yext to SVP of Global Revenue at Legora (06:50) Selling SaaS vs AI: Why It's the Best Time to Be a Seller (12:00) The Last Mile Problem in Vertical AI Sales (18:00) How Deal Velocity Has Changed with AI (26:00) Discovery, Change Management & Why MEDDICC Isn't a Sales Process (34:00) Chris Degnan's "Make It Snow" and Snowflake's GTM Playbook (42:00) PLG vs Enterprise: The False Tension (55:00) Basketball Talk: Jalen Brunson, the Knicks & NYC Sports (58:00) Creative Ways to Break Through & Get a Response 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 & SaaS startups) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today. No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts. About Vibescaling: Vibescaling is an advisory, recruiting, media, & investing firm for seed through series C AI-natives & fast-growing SaaS startups scaling from 0 to $100M ARR. Where to Find VibeScaling: | |||
| How I Broke Into VC From Sales With Liam Mulcahy, Operating Partner @ Kleiner Perkins | 15 Jan 2026 | 01:09:04 | |
Episode Description: Liam Mulcahy is an Operating Partner at Kleiner Perkins, where he leads go-to-market strategy for their portfolio companies from Series A through C. Before Kleiner, Liam was an early member of the GTM ops team at Unusual Ventures where he served as the first sales rep for 26+ portfolio companies simultaneously, building their GTM motions from zero. He cut his teeth at MongoDB pre and post-IPO, where he went from being told "we don't think you can cut it" to becoming a top performer and sales leader. Liam is one of the most thoughtful and intelligent voices on zero-to-one sales, career strategy, and what it actually takes to break into venture capital from an operating background. Discussed in this episode:
Episode Timestamps: (00:00) Liam's Journey: From D1 Track Athlete to Kleiner Perkins Operating Partner (06:00) Why Advertising Taught Him Sales (Without Realizing It) (10:00) The Tim Ferriss Books That Sparked the Startup Bug (14:00) What Made MongoDB's Interview Process Hard (In A Good Way) (18:00) The Cardboard Cutout That Changed Everything (24:00) Treat Your Interview Like a Deal: Getting Feedback After Rejection (31:00) Dealing With Imposter Syndrome (36:00) "If You're Going to Do Something, Do It Well" - The Flashcard QBR Story (40:00) Why Liam Didn't Want to Be a CRO (45:00) Cold Calling the Midas List to Break Into VC (50:00) How Kleiner Uniquely Positions The VC Operating Model (57:00) Why a Signed Contract is Your Best Competitive Moat (62:00) How to Actually Break Into VC (Step by Step) 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 & SaaS startups) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today. No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts. About Vibescaling: Vibescaling is an advisory, recruiting, media, & investing firm for seed through series C AI-natives & fast-growing SaaS startups scaling from 0 to $100M ARR. Where to Find VibeScaling: | |||
| From $2M to $950M ARR: How Kyle Parrish Built Figma's Sales Machine - Vibescaling Podcast Episode #3 | 08 Jan 2026 | 00:58:33 | |
Episode Description: Kyle Parrish was the third sales hire at Dropbox and the founding sales leader at Figma, where he scaled the business from $2M to $950M in ARR over six and a half years through their IPO. Before Figma, Kyle opened Dropbox's Austin office and hired 150 people in under two years. He's now advising and investing in top AI-native startups. Kyle is one of the most thoughtful go-to-market leaders in the game - his frameworks on PLG-to-enterprise, founder-led sales, and building high-performing teams are pure gold. Also, shout out to our awesome sponsor for this episode, Kondo. Think of it like Superhuman for LinkedIn messages - if you're terminally on LinkedIn like I am and your inbox is becoming unwieldy, give it a try for the first month free using this link - it saves me over an hour a day.
Episode Timestamps: (00:00) Kyle's Journey: From Dropbox's Third Sales Hire to Figma's Sales Leader (06:00) When Should Founders Hire Their First Head of Sales? (12:00) The Hardest Part of Founder-Led Sales Transition (18:00) PLG to Enterprise: Why You Might Want the Top-Down Seller (24:00) Building Dropbox Austin: 150 Hires in Under 2 Years (30:00) How Kyle Spotted Figma Before Anyone Else (The 3 Trends) (36:00) Scaling Figma from $2M to $950M ARR (42:00) "Stay Low at the Highs, High at the Lows" - Surviving the Roller Coaster (48:00) Why Founders Pitch Too Early (The Discovery Trap) (53:00) What Kyle Would Tell His Younger Self 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 & SaaS startups) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today. No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts. About Vibescaling: Vibescaling is an advisory, recruiting, media, & investing firm for seed through series C AI-natives & fast-growing SaaS startups scaling from 0 to $100M ARR. Where to Find VibeScaling: | |||
| This Week In GTM Episode #2 (Featuring Brendan Short of The Signal) - 12/5/25 | 18 Dec 2025 | 00:50:34 | |
Timestamps: (00:00) Intros (04:00) Vercel's AI SDR: Replacing a 10-Person Team with One GTM Engineer (08:00) When Should Founders Hire Their First Salesperson (11:00) "Sales Teams Should Be Indistinguishable from Product Managers" (14:00) What Does "Consultative Selling" Actually Mean? (18:00) The YC Founder GTM Playbook: LinkedIn-First Outbound (20:00) Why LinkedIn Content Beats Cold Email (26:00) Network-Led Growth: Why Warm Intros Still Win (30:00) "Climbing Cringe Mountain" - Why Posting on LinkedIn Works (34:00) Content as a Recruiting Superpower (38:00) Why Is Everyone Calling Sales "GTM" Now? (44:00) Ramp Shut Down Their Outbound Automation Team - Here's Why Episode Description: In this episode of "This Week in GTM," Chris, Cailen, and special guest Brendan Short (The Signal newsletter) break down the tweets they've been texting each other all week and share unfiltered takes on the evolving state of go-to-market. Discussed in this episode:
Host Links: About 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 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 Company Page - / vibescaling YouTube - / @vibescaling Newsletter - GTMBA - https://www.gtmba.ai/ Website - https://www.vibescaling.ai/ | |||