We have been the ones who have to make it work.
Caio is Greg and David: two co-founders who find the useful work, build the system, and stay accountable for what happens after launch.
Two founders
Caio was founded by Greg and David. We work as a small, senior team: close enough to understand how a business actually runs, and technical enough to build the system ourselves.
Clients work with the founders, from the first assessment through the build and handoff. There is no strategy team passing the work to someone else.
Greg’s background
Greg is a Seattle-based technologist with thirty years across engineering, product, and go-to-market. He is currently co-founder and CTO of Scribbl. Before that he co-founded Onder as its CTO, which was acquired by EasyKnock.
Along the way he was Chief Revenue Officer at DevHub, VP of Product at Angi and at Outreach, Head of Global Flights Shopping Product at Expedia, and a founding member of the AI team at Compass. He studied at the University of Washington.
Why a fractional Chief AI Officer
Most businesses that need AI expertise cannot justify hiring for it. The role is real, but it is not forty hours a week, and the people who can do it well are expensive and already employed.
A fractional arrangement fixes the mismatch. You get senior operators who have shipped software at scale, who can tell the difference between a technology that is ready and one that merely demos well, and who are accountable for outcomes rather than recommendations — for a few days a month.
Custom software used to be out of reach for most businesses. That is changing. Combined with agents that can carry out tasks across systems, software built around your operations can change how the business runs. Most owners simply do not have anyone whose job it is to notice that.
The hotel
During the pandemic Greg restored a vintage mid-century modern hotel on the Washington coast. He then automated much of its operations with custom AI agents and workflows — door access, guest communication, network maintenance, marketing.
Roughly 95% of guest interactions now happen without a person. It is a useful proof point because the building, the operating costs, and the nights on call were real before the systems took over.
How we work
We start by learning how the business actually runs, which is rarely how the org chart says it runs. Then we are direct about what is worth automating and what is not. Plenty of things are cheaper to leave alone.
What we build is meant to be handed over. Documentation, training, and systems your team can change without us. If the engagement works, it ends.
Greg’s experience
- ScribblCo-founder & CTO · Current
- OnderCo-founder & CTO · Acquired by EasyKnock
- DevHubChief Revenue Officer
- AngiVP of Product
- OutreachVP of Product
- ExpediaHead of Global Flights Shopping Product
- CompassFounding member, AI team
17 podcast appearances and features in Business Insider, NewsNation, and Commit 250.

Tell us how the business runs.
Thirty minutes, no deck. If we cannot help, we will say so.
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