A fractional chief AI officer who can also ship.

Senior ownership of your AI program, part time: the strategy, the roadmap, the vendor calls, the governance, and the board update, backed by a team that can build what the roadmap says instead of handing you a deck.

01why now

Every leadership team is now being asked what its AI plan is: by the board, by investors, by customers, and by employees who are already using AI tools whether there is a policy or not. Large companies are hiring chief AI officers. A mid-sized company usually cannot justify that full-time hire, and probably should not: the job is intense for the first year, while the roadmap and the foundations are set, and lighter after that.

The alternative most companies fall into is worse: AI handed to the CTO as a side project, or to whoever is most enthusiastic, with no budget, no authority, and no one checking whether the pilots return anything. A fractional AI officer gives you real ownership at the level of commitment the stage needs.

02what the role covers

• Strategy and roadmap. Where AI earns or saves money in your business, ranked by return and effort, with a twelve month roadmap the leadership team agrees to.
• Build versus buy. Which problems a tool you can buy solves, which need custom AI development, and which are not worth solving yet.
• Vendor management. Evaluating AI platforms and agencies, negotiating scope, and holding them to outcomes, including us.
• Governance. An AI usage policy, data handling rules, review steps for anything customer facing, and a record of what is running where.
• Adoption. Making sure the tools you pay for get used, through training on real work and champions inside each team.
• Reporting. A plain account to the CEO and the board of what was spent, what shipped, and what it returned.

why it helps that we also build

An advisor who has never shipped tends to produce roadmaps that are expensive to execute and hard to check. Because Insomnia Club builds software, the person setting your roadmap knows what each item costs to build, how long it takes, and where it usually goes wrong. When the roadmap calls for a build, you can hire our team, another firm, or your own engineers. That choice stays yours.

03who this is for

CEOs and COOs of companies roughly between $10M and $500M in revenue that have no one senior owning AI, or have someone owning it on top of a full-time job. It also fits private equity backed companies with an AI line in the value creation plan; see AI for private equity portfolio companies. For the wider view of how mid-sized firms should buy AI help, read AI consulting for mid-sized companies.

The model is close to how we have served as fractional CTO before. For Nestwell we owned the technical decisions a founding CTO would own, what to build first, what to defer, and how to spend a $30K budget, and the company raised $1.2M+ after shipping.

04how it runs

1. First 30 days: diagnose. Interviews with leadership and the teams, a review of current tools, spend, and data, and a ranked list of opportunities with what each is worth.
2. Days 30 to 90: commit. The roadmap, policy, and budget agreed with leadership, the first one or two projects started, and quick wins from existing tools shipped.
3. Ongoing: run the program. A fixed monthly commitment: regular leadership check-ins, vendor and project oversight, adoption work, and a written update you can hand to the board.
4. Hand-off. When the program is big enough for a full-time leader, we help you write the role, hire for it, and hand over.

Like every engagement, the commitment and the fee are fixed before work starts.

05common questions about fractional chief AI officers

What is a fractional chief AI officer?

A senior leader who owns a company's AI program part time: strategy, roadmap, vendor decisions, governance, adoption, and reporting to the CEO and board. It gives a mid-sized company executive ownership of AI without a full-time executive hire.

When does a company need a fractional chief AI officer?

When AI is on the board's agenda but no one senior owns it, when pilots are running without anyone measuring their return, when teams are using AI tools without a policy, or when the CTO has AI on top of a full-time job.

How is this different from an AI consultant?

A consultant typically delivers a recommendation and leaves. A fractional AI officer stays accountable for the program over time: running the roadmap, managing vendors, and reporting what was spent and what it returned.

Do you only recommend your own services?

No. When the roadmap calls for a build, you can hire our team, another firm, or your own engineers. Part of the role is holding every vendor to outcomes, including us.

How much time does a fractional chief AI officer spend with us?

More in the first ninety days, while the roadmap and foundations are set, then a fixed ongoing commitment sized to the program. The commitment and the fee are agreed before work starts.

What happens when we need a full-time AI leader?

We help you define the role, hire for it, and hand over the roadmap, policies, and vendor relationships so the new leader starts with a working program.