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Chief AI
Officer.
On your team.
AI, handled.

Your company gets a Chief AI Officer on its leadership team: someone senior who sorts out where AI actually belongs in your business, gets your people using it safely, and builds the software himself when something's missing. That's Chris Boylan, three-time CTO.

Chris Boylan

Chris Boylan · 3× CTO · 20 years

Led engineering at

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

What your
Chief AI Officer
actually does

Every part of your business is being pitched AI right now, and every vendor swears theirs is the answer. Someone senior should be deciding what's actually worth it. In a small to medium sized company, that person usually doesn't exist, so the decisions land on you.

That's the seat Chris takes. He sits on your leadership team on an ongoing retainer, a few days a month, and owns AI for the company: which tools are worth it, which aren't, how your data stays safe, what your team should be doing differently by next quarter, and where the real opportunity is.

And when the right answer is software that doesn't exist yet, you don't get a brief handed to some other vendor. He builds it. Twenty years of engineering means you get someone who knows what's hard, what's easy, and what's a waste of your money.

How it works

  1. 1One free call

    A call with you, on the phone or on video, about what's actually going on in your business and where AI could help. No pitch deck. If it's not the right fit, you'll hear that on the call.

  2. 2A seat at the table

    Chris joins your leadership team as Chief AI Officer on a monthly retainer. Together you decide what to fix first, and your team gets someone working alongside them, in plain English, at a pace they can absorb.

  3. 3Built when it needs building

    Not every problem in your business has an off-the-shelf answer. When yours doesn't, Chris builds one. Using AI, he creates custom software in a fraction of the time it used to take a team, and it often fits far better than anything you could buy.

The record

Twenty years
as a software engineer
Three time CTO
Chief Technology Officer at three companies

Twenty years as a software engineer and three-time Chief Technology Officer. Chris has led the engineering teams at Rolling Stone, Us Weekly, Fatherly, CAFE, Daily Dot, and Nautilus.

He has led AI adoption inside companies before and shipped AI-powered software to production. He runs his own work on AI every day, including building this website with AI coding agents, so what your company gets is what he actually uses, not what he's read about.

You get plain English, and you get told when something is a bad idea instead of being sold it.

Let's talk about
your business.

One free call about your business. Chris takes three of these a week, so yours gets his full attention. Bring the messy version; that's the useful one.