From No Fees to AI Agents: Ex-CEO Brett Keller’s 26 Years at Priceline

When Brett Keller joined Priceline as marketing director in 1999, it was the third-largest U.S. online travel agency behind Travelocity and Expedia, and was selling Name Your Own Price airline tickets.

When Keller finished his 10-year run as CEO last month, Priceline was still selling flights — albeit in a more conventional fashion — and it offered 1.2 million accommodations in 166 countries as a brand within the world’s largest travel company, Booking Holdings.

In a recent Skift interview, Keller reflected on his tenure at Priceline, recalling how the company undercut Expedia by becoming the first OTA to eliminate flight booking fees and redefined brand marketing with the iconic Priceline Negotiator campaign with William Shatner.

He detailed how Priceline’s Penny chatbot has a dozen AI agents surrounding it, handling everything from shopping to cancellations. On the various LLMs’ agentic efforts, Keller said non-travel companies have never commit