Ep. 597 - You.com COO Alex Triplett - How To Make or Break a COO in The First 90 Days

What if walking away from the CEO seat was the smartest career move you could make in AI right now?

Cameron Herold sits down with Alex Triplett, COO of you.com, the company quietly powering web search for AI agents behind brands like Salesforce, Anthropic, and Harvey. Alex turned down the chance to be a CEO to take the second-in-command seat at a fast-moving AI startup, and he explains exactly why.

They get into the operator work most leaders avoid: walking into a 135-person company, making a brutal focus call, and rebuilding the team around a single mission. Alex breaks down his first 90 days, the listening tour that validated his biggest decision, how he sells to enterprise without getting strung along, and the system that keeps him out of the minutiae.

Skip this one, and you risk what most new executives do: the right idea at the wrong time, and broken trust. Listen now for the unfiltered COO playbook on focus and timing.

Sponsored byGenius Network - An exclusive community for highly successful entrepreneurs, connecting you with top-tier leaders, strategic insights, and powerful relationships to help you grow your business faster and smarter.

Learn more: https://www.geniusnetwork.com/

Timestamped Highlights10:16 – “Google for AI agents,” explained: the invisible layer your favorite LLM cannot work without

13:18 – You might be using you.com right now without knowing it. Here is where it hides in the AI stack

15:08 – How to tell a real enterprise deal from a buyer who is just keeping you busy

19:56 – The COO superpower hiding in plain sight, and why it gets you a seat at the C-suite table

23:08 – Chief of staff or glorified executive assistant? The title too many companies get wrong

25:24 – Three companies, one founder: how Richard runs you.com while raising $650M for a frontier lab