The Crew Podcast

Maia Josebachvili is CRO of Stripe AI and CRO of Stripe's revenue suite. Her path started as a trader on the stock exchange floor, then went through founding a company and serving as CMO at Greenhouse, before 8+ years and 5 different jobs at Stripe. She joined when Stripe had about 1,000 people, and it's now over 10,000. Today she has a front-row seat to the fastest-growing AI companies in the world: the top 100 AI companies on Stripe are growing 195% year over year, up from 145% a year ago, and 48% of their revenue comes from outside their home market. Her sales strategy slide this year says "Don't sell anything," and her reps are well above quota.

Discussed in This Episode:
• Why the top 100 AI companies on Stripe are growing 195% year over year
• AI companies going global from day one, and why Brazil and India are markets they can't miss
• Building PLG and enterprise sales at the same time
• Agents as the third buyer, and agent traffic to Stripe's docs
• Why AI pricing landed on hybrid: a platform fee plus usage on top
• Why outcome-based pricing mostly stuck in customer support
• "Don't sell anything," and how reps acting as growth consultants still beat quota
• The local payment methods and checkout tweaks that move revenue
•Stay conversations, and why reps love working with the product team
• How Stripe's sales team uses its internal AI hub
• What separates Stripe's best sellers

Timestamps:
• (00:00) Your incentives have to be aligned
• (01:29) Welcome to the Crew podcast
• (03:40) From the stock exchange floor to CRO
• (06:04) How AI natives are commercializing
• (08:18) Agents are the third buyer
• (12:55) Why AI companies go global so fast
• (15:06) How AI companies are pricing now
• (16:32) What happened to outcome-based pricing
• (19:22) Don't sell anything
• (21:13) Local payment methods that move revenue
• (24:01) Stay conversations and hiring Stripe sellers
• (28:19) How Stripe's sales team uses AI
• (32:09) What Stripe's best sellers do differently
• (37:54) The bets Stripe got wrong, and agentic payments

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/

Recorded live at Park Paddle on the Embarcadero in San Francisco, this special edition of This Week in GTM comes from Crew’s second GTM Paddle event. After the first in New York, we brought the series to the Bay Area, the hub of AI startups, with around 100 enterprise AEs and sales leaders, a DJ, food, and drinks.

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, heading up Crew’s BD practice. Ten years in SDR leadership, and hiring was always his favorite part.
Cailen DSa, 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 guest appearances from Marc Goldberger, VP of Sales at MetaView, and John Boyer, VP of Sales at Blacksmith.

Discussed in This Episode:
Why former bankers, consultants, and lawyers may be the best salespeople of the AI era.

If a company won’t pay above market for a hunter AE role, it’s a red flag

Marc Goldberger on MetaView growing

Paraform’s index and which AI-native sales teams stand out

The new em dash of AI: 47-point Claude memos

What Anthropic’s IPO means for AEs who joined early

What the best recruiters do, and what the best candidates do

How Crew uses AI agents

John Boyer on why AI coding made CI the new bottleneck

The one diligence question to ask before joining a startup

EQ, IQ, and AQ: the three pillars for interviewing AEs

Favorite Crew clients

Timestamps:
(00:00) Episode Preview

(01:49) Welcome to the GTM Paddle Event in SF

(03:53) Why Ex-Bankers, Consultants & Lawyers Make Great Sellers

(07:34) Hunter AE Pay and Inbound vs. Outbound

(14:17) Marc Goldberger on the Hiring Market and MetaView

(16:27) AI-Native Sales Teams and Talent Density

(21:31) Why the Top Talent Wants AI Jobs

(26:55) The New Em Dash of AI

(30:24) Rocket Ships, “Zero to One,” and the Anthropic IPO

(37:04) What the Best Recruiters and Candidates Do

(50:34) AI Agents in Recruiting and Everyday Work

(1:01:54) John Boyer on Blacksmith

(1:06:41) Corgi and the Ideal Sales Role Checklist

(1:09:10) The One Diligence Question to Ask Before Joining a Startup

(1:14:04) Never Leave a Meeting Without the Next Meeting Booked?

(1:18:14) Favorite Client Companies

(1:19:48) Closing

Blogs mentioned in the Podcast:

Why Join Blacksmith:
https://www.withcrew.blog/p/why-join-blacksmith 
12 Things Top GTM Interviewers Are Doing In 2026 To Land Offers:
https://www.withcrew.blog/p/12-things-top-gtm-interviewers-are-doing-in-2026-to-land-offers 

Thanks to our sponsors: Fireworks, Listen Labs, Serval, Greptile, MetaView, Blacksmith, Nooks, and Centralized.

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/

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.
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/

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
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/

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.

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/