16 Jul 2026 07:00
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.
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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
33:34 – 135 people on day one: the focus call that cut the team to 110, then built it back stronger
38:01 – One mission, one North Star, and the moment focus “just exploded” the company
39:23 – The first 90 days that make or break a COO: the listening tour that validated everything
47:23 – Why this COO leaves messages unread on purpose, and what it taught him about good decisions
50:09 – The one-sentence piece of advice he would give his 22-year-old self
About the GuestAlex Triplett is the Chief Operating Officer of you.com, the leading web search API for AI agents, serving customers like Salesforce, Anthropic, and Harvey. An investor turned operator, Alex spent the first decade of his career in private equity before moving to the operating side. He served as Global Head of Corporate Development at ION Group, where he helped grow the business from $150 million to $3 billion in revenue, and later as CFO and COO of Appfire. He also chairs the board of the travel app Pangea and holds a degree from the McIntire School of Commerce at the University of Virginia.
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