Chris Boylan workingopen.com

Chief AI Officer at Working Open

Chris Boylan

I run Working Open, where I take the Chief AI Officer seat on the leadership teams of companies with 10 to 100 people.

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Chris Boylan

Twenty years building software. Three-time CTO.

I've spent twenty years as a software engineer and have been Chief Technology Officer at three companies. I've led the engineering teams at Rolling Stone, Us Weekly, Fatherly, CAFE, Daily Dot, and Nautilus. I have taken companies through AI adoption from the inside and put AI-powered software into production, and I use these tools in my own work every day, including to build this page.

Working Open is where that experience goes to work for smaller companies. I sit on a leadership team a few days a month, own the AI decisions from what to adopt to what to ignore, and when the right software doesn't exist yet, I build it myself.

  • Rolling Stone
  • Us Weekly
  • Fatherly
  • CAFE
  • Daily Dot
  • Nautilus

More at workingopen.com About me at Working Open LinkedIn GitHub Contact

Before Working Open, this site was my blog. The older writing and audio are still here: the blog archive, the audio archive and the forum archive, 2003–2009.