New episode on the Crew Podcast - Steve Pascucci, VP of Global Sales @ Outtake.
Also, shoutout to our sponsors for this episode, Parallel & Attention. Been awesome working with both of these teams for recruiting, and now infusing as part of our media arm.
Both incredible products used by a bunch of the AI-natives we work with.
Parallel: Where AI agents find answers - a web index built from the ground up for AI. GTM engineers use it to run real-time account monitors (funding rounds, exec changes, product launches) and automate research and enrichment at scale. Get started for free @ https://parallel.ai/
Attention: Put a team of revenue agents on every deal. They capture all your customer interactions (without a bot), update your CRM, best engage on your deals, cleanly automate all reporting, score opportunities and reps against any framework, and forecast in a way you can actually trust. The fast-growing companies like Lovable, Avoca, Abridge, and hundreds of others rely on them. Try them today at attention.com
Some of our previous guests:
Eleanor Dorfman, Head of Commercial Sales @ Anthropic
Pat Forquer, CRO @ Legora
Graham Moreno, VP of GTM @ Parallel
Tomer Chernia, VP of GTM @ Cursor
Liam Mulcahy, Head of Sales @ Parallel (former GTM Operating Partner @ Kleiner Perkins)
Becca Lindquist, Head of Sales @ Clay
Nick Bogaty, CRO @ Vercel
Kyle Parrish, former VP of Sales @ Figma
Ghazi Masood, CRO @ Replit
Evan Cassidy, VP of Sales @ Decagon
James White, VP of Sales @ Rogo
Mark Ebert, SVP of Revenue @ Profound
Rob Saliterman, VP of Sales @ Harvey
Bardia Shahali, VP of Sales @ Granola
And many more in the pipeline - if you know any good leaders who fit this, shoot me a DM/reply/email ( [email protected] ). We’ll keep openings rolling and be super open to suggestions for similar guests.
We film in-person in SF & NYC at legit podcast studios and have retained a stellar post-production agency, so the quality will be high.
Steve’s Background
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.
Discussed In This Episode
Why the champion answering all your emails is usually the wrong one to bet on
The Workday deal Cloudflare had almost no business winning, and the person in the corner of the room who made it happen
Selling one level below the C-suite, where he says the magic happens
Why CVE reports spiked almost 10x, and the 2 to 5% that are actually weaponized
How threat actors now build pixel-perfect impersonations at machine speed
Creating urgency without ambulance chasing when you can already see a prospect’s exposure
Why security still runs through the channel, and why he thinks the channel is ready to be reinvented
Cloudflare’s early mistake of mistaking good timing for a pattern
Why the path that looks scariest internally is the one that gets you ahead
The hiring red flags he screens for, and the best answer he’s heard to “how do you use AI?”
Why he’s considering blocking AI tools for new hires in their first month
Convening power vs. economic power, and knowing where your buyer sits in the budget cycle
Key Timestamps
(06:38) Pixel-perfect impersonations at machine speed
(15:33) Selling middle out
(16:59) The champion in the corner of the room
(19:30) Creating urgency without ambulance chasing
(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
Thanks for tuning in!
If you enjoy it, please give us a rating, review, or follow on Spotify/YouTube/Apple Podcasts - it really helps us grow this.
For those who are new, my name is Chris Balestras, co-founder & head of talent, media, & brand @ Crew - a GTM recruiting, media, and investing firm, working with seed through series D AI-natives to help them grow.
Where to find Crew:
We work with many of the hottest AI-native startups in various capacities, and for those who are interested, shoot me an email at ( [email protected] ) or a DM on LinkedIn.
🫡 cheers,
Chris