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/

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