Ryan launched the Dilbert website, based on the popular comic strip created by Scott Adams.
[2] Serving as senior VP of business and finance, he helped lead a restructuring effort that increased United Media's profits fivefold.
DoubleClick was sold in 2005 for $1.1 billion to Hellman and Friedman LLC, and Ryan stepped down as CEO shortly thereafter.
[5] During this time in career, Ryan also served on the boards of the Direct Marketing Association, the Ad Council, and HotJobs.
Gilt offers fashion for women, men, and children; home decor; artisanal ingredients; hotels and travel experiences on every continent.
Ryan served as chairman of the board through the company's initial public offering in 2017 at a $1.18 billion valuation.
[10] Ryan has gone on to found and serve as chairman of the board for several other New York–based companies including, Zola, Coedition, Nomad Health, and Meetup.
[11] Ryan was a founding advisor and seed investor for Pearl Health, before participating in the company's Andreessen Horowitz-led Series A fundraise, alongside AlleyCorp.
He has been named the director emeritus of Human Rights Watch as well as being on the advisory board for Doctors Without Borders.