About Chief Of

Senior AI leadership for the other 99% of companies.

The Fortune 500 hired their Chief AI Officer last year. Everyone else is stuck between vendors selling tools and consultancies selling decks. Chief Of exists to give mid-market companies a third option: a senior fractional CAIO who designs the strategy, builds the agents, and is accountable for the outcome.

Why this exists

AI is no longer optional. In 2026 a board chair asking "what's our AI strategy?" is as routine as asking about pipeline or cash. But the market response has been confusing: an explosion of point-solution SaaS, a wall of generic consultancy decks, and a price tag for full-time AI executives that only fits a handful of companies on the planet.

The companies in the gap, anywhere between $5M and $100M in revenue, are stuck. They know AI matters. They don't have a credible senior voice in the room. And the consultants they call are either too junior to land in their boardroom or too senior to actually build anything.

Chief Of was built for those companies. One senior operator, accountable end to end, on a retainer that costs a fraction of a full-time hire.

What "Fractional CAIO" actually means here

A Fractional Chief AI Officer at Chief Of is a senior AI executive who sits at your leadership table on a part-time basis. They own your AI strategy and roadmap, design and oversee the build of custom agents on infrastructure you control, report quarterly to your board, and stay accountable for measurable outcomes: typically increased capacity, reduced cost, or new revenue.

We are not a consultancy that hands you a deck. We are not a vendor reselling someone else's platform. We are not "AI advisors" who show up for monthly calls. We are an operating function: fractional in time, full in accountability.

Brian Schmitt, Founder & Principal CAIO of Chief Of

Brian Schmitt

Founder & Principal CAIO

Chief Of is founded and led by Brian Schmitt, an operator who has spent more than two decades turning data into decisions for brands people actually know, including Peak Design, Hydro Flask, Brooklinen, and OXO. He ran his first A/B test in 2003 by hardcoding the randomizer into the page and piping the results to Webtrends, because Google Analytics didn't exist yet. He's been building measurable, production-grade systems ever since, a pioneer of experimentation and conversion-rate optimization long before either had a name.

That same instinct is exactly what AI demands and rarely gets: ship something real, measure it, and let the data settle the argument. Brian's thesis is simple. The playbook that works for the Fortune 500 (disciplined strategy, vendor-neutral architecture, real production agents, executive-level governance) works just as well for mid-market companies. It just has to be delivered fractionally, by one senior person, on a price tag that fits a $20M company. So that's the practice he built.

Brian is also available to be booked for speaking engagements and panels on AI implementation. A longer bio and prior work is available on request during a strategy call.

Operating philosophy

Five principles run through every engagement. They are choices, not features, and they're the reason we look different from a big-firm consulting engagement on the inside.

Principle 01

Ship in 90, not 180.

A production agent in 90 days, not a strategy phase in 180. Strategy is real only when something is running.

Principle 02

One senior, accountable.

One Fractional CAIO owns the engagement end to end. No partner-sells, junior-builds, hand-off carousel.

Principle 03

Vendor-neutral on purpose.

No referral fees, no kickbacks, no "preferred platforms." We recommend what fits your stack and walk away if you choose differently.

Principle 04

Compliance is upstream.

SOC2 and HIPAA-readiness designed in from day one, through partners with audited controls. Not retrofitted at the end.

Principle 05

Your team owns the work.

Internal fluency is a contractual deliverable. We don't keep the keys, and we don't lock you into a multi-year retainer.

Principle 06

Measure in dollars.

Every production agent gets an evaluation framework and unit economics in dollars. If it doesn't pay back, we sunset it.

Want to see if we're a fit?

A 30-minute strategy call. No pitch deck, no obligation. Honest answer or honest referral.

Book a Strategy Call →