The Crew Podcast

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/

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.
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/

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.
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/

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/