The Crew Podcast interviews GTM leaders and investors at top AI startups and early-stage companies.
Every week, host Chris Balestras, co-founder @ Crew (a GTM recruiting, media, & investing firm for seed through series D AI-natives) sits down with operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today.
No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.
Find us @ https://www.withcrew.ai/ & https://www.withcrew.blog/
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Données mises à jour le 05/11/2026
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Why Inference Is the Hottest Market in AI Sales Right Now | Soumya Tulloss, SVP Sales @ Fireworks AI
mardi 3 novembre 2026 • Durée 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 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.
How to Build a Sales Team With No Sales Engineers w/ Steven Boone, VP of Enterprise GTM @ Perplexity
mardi 27 octobre 2026 • Durée 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
The Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies.
This Week in GTM w/ Glenn Rachlin (OpenRouter) | Factory vs Cognition, AI GTM Talent Density, & More
jeudi 22 octobre 2026 • Durée 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.
After building his career in crypto, including his time at Alchemy, Glenn has shifted his focus to AI, which he considers the most important technology in history. Now at OpenRouter, he operates at the intersection of AI infrastructure, enterprise sales, and the rapidly evolving ecosystem of AI-native companies.
A student of go-to-market strategy and sales culture, Glenn has a front-row seat to the people, companies, and ideas shaping the next generation of tech. From the rise of AI-native sales teams and the talent wars unfolding across the industry to the unfiltered world of GTM Twitter, he brings a perspective shaped by years in crypto and a new chapter in AI.
Discussed in This Episode:
The Factory vs. Cognition controversy
Why GTM Twitter is where the conversation happens
AI memes and the “butthole era” of logos
How to identify top GTM talent in AI
What makes a sales team AI-native
Why being an order taker can be better than being a hunter
Why hunter AEs should earn more
Glenn’s shift from crypto to AI
What OpenRouter does and how it works
How AI agents are changing everyday work
Timestamps: (00:00) Episode Preview (01:33) Welcome to the Crew Podcast (05:15) Factory vs. Cognition (13:04) GTM Twitter and AI Memes (20:18) AI Agents in Everyday Work (27:48) AI Talent and GTM Teams (31:30) Why AI Matters (33:00) GTM Culture and Memes (39:33) Why Order Taking Is the Best (44:05) The Hunter AE Debate (47:26) From Crypto to AI (50:22) Closing Remarks
About The Crew Podcast The Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies.
From Yale Engineer to 3 IPOs: How to Hire the Right Rep for Your Sale | Rich Liu, ex-Navan CRO
mardi 20 octobre 2026 • Durée 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
Why Most AI Startups Aren't Defensible & Why Sales Teams Fail w/ Brendon Cassidy, Founding GTM @ LinkedIn
mardi 13 octobre 2026 • Durée 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
Cyber Risk Has Never Been Higher & Selling Cyber 101 w/ Steve Pascucci VP of Global Sales @ Outtake
mardi 6 octobre 2026 • Durée 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
Live Podcast: The GTM Rebrand, CRO Musical Chairs & Talent Mafias @ Reserve Padel NYC
jeudi 1 octobre 2026 • Durée 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 Chris Balestras, Partner at Crew, hosting. Started at Salesforce, moved into early-stage sales, then founded Crew.
Curt Clauss, Partner at Crew, heading up the AE and sales leadership practice. Twelve years in tech sales across Series A through E, including runs at Harvey and Outreach, plus founding AE experience.
Matthew Roberts, Crew's SDR leadership practice, three months in. Ten years in SDR leadership, and hiring was always his favorite part.
Caitlin Desai, Co-founder at Crew, running exec recruiting. Seventeen years as a GTM IC and leader at Bay Area companies including Box and Dropbox, and watched a company go from $1M to $1B in ARR.
Plus drop-ins from Mark Ebert of Profound and George of Basis, Head of GTM.
Discussed in This Episode:
- Why Paul Graham thinks “GTM” sounds bogus, and why Crew is doubling down with 200 hats
- The Stripe origin story of the GTM rebrand, and why every AI native inherited it
- CRO musical chairs at the labs: Paul Smith, Denise Dresser, and Dolly's arrival
- How Wiz ran the equivalent of a six-to-twelve-month enterprise sale in six days
GTM Roundtable: The State of AI-Native Sales w/ Clay, Parallel, Avoca & Profound
mardi 29 septembre 2026 • Durée 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
The Science of Sales + Why Founders Hire Sales Too Early w/ Mark Roberge, Stage 2 Capital
mardi 22 septembre 2026 • Durée 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
Building GTM Agents Live + The AI-Pilled AE Operating System w/ Nic Siegle, Founding AE @ Dust
vendredi 18 septembre 2026 • Durée 01:02:25
Nic's Background Nic Siegle is a founding account executive at Dust, the Series B, Sequoia-backed platform for teams of humans and teams of agents. He has been there about a year, placed by Crew's recruiting practice, and came in from a product-led background at Mixpanel and Asana, where product usage data was the bread and butter. He describes himself as a tinkerer who cannot imagine a better tool to play with, and he runs his own account executive operating system inside Dust: a morning briefing delivered as a podcast, an Eisenhower matrix of AI recommended actions, live account plans with org charts, and a fresh AI generated seagull every day because life is short.
Timestamps(00:00) The wrong thing at amazing scale
(01:30) Welcome to the Crew podcast
(02:31) Why Crew wanted to try a live demo episode
(03:56) Nic's background, and what Dust actually is
(06:11) The three stages of AI adoption inside companies
(07:39) Open source Chinese models, and sitting on top of every model
(08:30) The MCP timeline, and when tools started talking to each other
(11:25) Was Opus the chasm?
(12:54) The core sales use cases, from ask-sales bots to RFPs
(17:10) Why "how AI pilled are you" is now an interview question
(18:06) How Clay and 1Password govern who builds what
(20:51) "Show me something you've built"
(22:04) Building a pre-call prep agent from scratch
(24:48) Picking a model, and the test that cost 178 times more
(31:07) Idiot in motion versus the blast radius of AI
(39:03) Setting a 7am trigger and emailing yourself the brief
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 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.
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.
• (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 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/
• (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.
• (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/
(44:48) Publishing an agent so the whole team can use it
(49:26) Nic's cockpit: Pods and an AE operating system
(55:36) Building an account plan with org chart and live product usage
(01:01:15) Where to try Dust
About The Crew Podcast The Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies.
Every week, host Chris Balestras, partner @ Crew, talks to the people actually building go-to-market motions in real time, not in retrospect.
About Crew Crew is a recruiting, investing, & media firm for seed through series D AI-natives & fast-growing SaaS startups.
This Episode Is Brought To You By Dust: The platform for teams of humans and teams of agents to work together. Build agents without writing a line of code, connect them to your company's data and tools, and run them from Slack, a spreadsheet, the Chrome extension, or your phone. Dust sits on top of frontier and open source models so you can pick the right one for each job, with permissions, governance, and human-in-the-loop controls set per action. Trusted by Datadog, 1Password, and Clay. Try it at https://dust.tt/
