🎙️ Learnings from Attio, Hex, and Segment: Hollie Wegman on Building the Operator Muscle

Hi, I’m Jan. After years as a Chief of Staff and Operations Lead at companies like Airbnb, I started The Operator to give a voice to the people leading, growing, and shaping high-growth tech companies. Every few weeks, I share stories from Operators who have helped build some of the most exciting organizations in tech.This is the first recorded podcast issue of The Operator. Find the written summary here.Hollie Wegman has been at the center of some incredible company-building stories. She helped scale Segment all the way to its $3.2B acquisition by Twilio, worked as an EIR at Redpoint, and most recently served as COO of Attio, the AI-native CRM that raised $52M led by GV (Google Ventures).Hollie recently left Attio to invest in and advise AI startups. For this episode of The Operator, we talked about what four years inside an AI-native rocketship taught her about the changing Operator playbook.In this episode, we cover:00:00 From Marketing to COO04:35 Scaling as Attio COO06:43 Jazz vs Symphony Ops08:27 North Stars in the AI Era10:10 The Invisible COO Work13:18 Hiring for AI Native Orgs16:42 How AI Changes GTM20:07 Hollie's Advising and Investing Thesis22:02 Everyone Becomes a COO24:23 Lessons from Segment and Hex26:17 Brand in an Agent World29:33 Curiosity as Superpower31:04 Closing Words and Where to Follow Hollie_Where to find Hollie Wegman:LinkedIn: https://www.linkedin.com/in/hollie/Dear Operator Newsletter: https://substack.com/@dearoperator_Where to find Jan:LinkedIn: https://www.linkedin.com/in/janrixgens/The Operator Newsletter: https://www.readoperator.com/X: https://x.com/jrixgens This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.readoperator.com