The Crew Podcast

https://www.withcrew.blog/p/why-join-blacksmith

Ex-Bankers as AEs, the Anthropic IPO & 47-Point Claude Memos | Live from Crew's SF Padel Event Nov 09, 2026

Show notes

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:

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/

Why Inference Is the Hottest Market in AI Sales Right Now | Soumya Tulloss, SVP Sales @ Fireworks AI Nov 03, 2026

Show notes

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.

Start for free at https://www.metaview.ai/

Where to Find Crew

How to Build a Sales Team With No Sales Engineers w/ Steven Boone, VP of Enterprise GTM @ Perplexity Oct 27, 2026

Show notes

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.

Start for free at https://www.metaview.ai/

Where to Find Crew

This Week in GTM w/ Glenn Rachlin (OpenRouter) | Factory vs Cognition, AI GTM Talent Density, & More Oct 22, 2026

Show notes

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

From Yale Engineer to 3 IPOs: How to Hire the Right Rep for Your Sale | Rich Liu, ex-Navan CRO Oct 20, 2026

Show notes

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
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.

Start for free at https://www.metaview.ai/

Where to Find Crew

Why Most AI Startups Aren't Defensible & Why Sales Teams Fail w/ Brendon Cassidy, Founding GTM @ LinkedIn Oct 13, 2026

Show notes

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
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

Cyber Risk Has Never Been Higher & Selling Cyber 101 w/ Steve Pascucci VP of Global Sales @ Outtake Oct 06, 2026

Show notes

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/

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 Oct 01, 2026

Show notes

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

- 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
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