// Service · Fractional CAIO

A fractional Chief AI Officer, in your leadership meetings.

Strategic direction and hands-on prototyping for funded teams that need an AI executive but not a $400K hire. Roy joins your weekly leadership cadence, ships alongside engineering, and owns the AI roadmap. One monthly retainer.

// The problem

A full-time CAIO costs $400K loaded and the role is too new to scope.

The Chief AI Officer is the youngest title on most org charts. Five years ago it did not exist. Two years ago it was a board-deck talking point. Now investors ask about it on every funding call, and founders are stuck deciding whether to hire one before they have a clear sense of what the person should own day to day. Base salary for a credible CAIO at a Series B in the US runs $250K to $350K. Loaded with equity, benefits, and recruiting fees, you are at $400K to $500K before the person has shipped a single agent.

The harder problem is scoping. A CAIO at a 5,000-person company runs an org. A CAIO at a 35-person company plays four roles simultaneously, half of which the founder used to own. Strategy, vendor selection, prototype building, hiring panel, board narrative. That is not one job, it is a portfolio of unfamiliar work, and most candidates with the title on their LinkedIn have never operated at sub-50 headcount. You end up paying senior-exec money for someone who needs onboarding to your stack and your customers before they add value.

So founders try to be the CAIO themselves. They block Thursday afternoons for "AI strategy," watch the time get eaten by sales calls, and end up shipping nothing. Or they hire a junior AI engineer and ask them to think like an executive, which never works. The middle option, a fractional Chief AI Officer who shows up in the room for the strategic decisions and the prototype work, is what most funded teams under 50 need in practice. We wrote about this category in detail in What Is a Fractional AI Department.

// Why fractional fits this role

Most of the CAIO job is concentrated in eight to twelve hours a week.

For a funded team under 50, the high-impact work of a Chief AI Officer compresses into a predictable weekly shape. One leadership meeting where AI direction gets debated and locked in. Two to three deep work sessions with engineering on whatever prototype is the priority that sprint. A vendor call or two. A memo. The rest of a full-time exec calendar gets filled with internal coordination that does not exist yet at your stage. You do not have an AI org to manage. You have a small team and a roadmap.

That compression is exactly why fractional works for this role specifically, in a way it does not work for, say, a fractional CTO at a hardware company. The strategic input is bursty. The prototype work is project-shaped. The hiring panel is a quarterly thing, not a weekly one. A fractional CAIO who shows up for eight to twelve hours a week gets to the same set of decisions a full-time hire would touch, without the fixed cost.

And the unit economics flip. A $400K annual loaded cost amortizes to roughly $33K a month. The same operator on a fractional retainer is a fraction of that, with no equity dilution, no recruiting cycle, and no six-month ramp. For a Series A to Series B team that needs AI direction now but does not have the AI surface area for a full-time hire, the math is not close. The risk profile is also lower because you can scope up or scope down month to month as the work changes.

// The work

Five things a fractional Chief AI Officer owns end to end.

Not a deck-only consultant. Roy sits inside your leadership cadence, ships alongside your engineers, and owns the AI roadmap as an executive would.

01

Weekly leadership meeting

A fixed seat in your weekly exec or leadership sync. AI direction, prioritization, what got built last week, what is shipping next. The CAIO voice in the room when product and engineering are arguing about scope. Calendar held permanently, not booked ad hoc.

02

Hands-on prototyping

When a prototype needs to ship in five days, Roy is in the codebase with your engineers. Agent design, model selection, eval harness, ship. Not a Notion brief handed to your team to figure out. Real PRs, real reviews, real shipping on your repo.

03

Strategic memos + investor-deck input

Monthly written memos on AI roadmap, build-vs-buy calls, and the competitive landscape in your category. Direct input on the AI sections of your fundraising deck and investor updates. Board-quality writing, not bullet points.

04

Vendor + tool selection

Model providers, agent frameworks, eval tools, observability, data pipelines. Roy runs the vendor calls, scores the options against your actual stack, and writes the decision memo. You stop spending Friday afternoons on AI vendor demos.

05

Hiring panel for AI roles

When you do start hiring AI engineers, ML leads, or eventually a full-time CAIO, Roy sits the panel. Technical screens, leadership interviews, reference checks. The job description, the rubric, the offer math. You get the role filled correctly rather than reactively.

// The shape of the engagement

What the calendar and the output look like in practice.

Honest numbers from current and recent engagements. Your shape varies by stage and roadmap, but the medians are consistent.

32 to 48
Hours per month
eight to twelve hours a week on average
6 to 10
Founder hours freed per week
reclaimed from AI strategy work
6 to 12
Months typical engagement length
most teams renew at the six-month mark
5 to 10
Days to first shipped prototype
from kickoff call to a working artifact
// Side by side

Hiring a full-time CAIO vs fractional CAIO with EOI.

Both options get you executive-level AI ownership. The cost, ramp, and risk profiles are not in the same category.

Hire full-time CAIO
  • $400K to $500K loaded annual cost
  • + 0.5% to 1.5% equity grant
  • 4 to 6 month executive search
  • 3 to 6 month ramp to full output
  • Fixed cost once hired, hard to unwind
  • Candidate may have never operated sub-50
  • Single bet on one person, single failure mode
  • Wrong hire costs 12 months and severance
Fractional CAIO with EOI
  • Monthly retainer, fraction of a full-time hire
  • No equity required
  • Engaged within two weeks of scoping call
  • Shipping in week one, prototype in days
  • Scope up or down month to month
  • Built for the funded-team-under-50 stage
  • Backed by the EOI bench for surge work
  • Cancel any time after first 60 days
// How it starts

From first conversation to steady state in four weeks.

Step 01

Week 0 · Discovery + scoping

A 90-minute scoping call with Roy. Stage, team shape, current AI surface area, the three decisions on your plate, the prototype you wish was already shipped. We agree the scope, the retainer, the cadence, and the first 30-day deliverables. A short written engagement memo follows within 48 hours.

Step 02

Weeks 1 to 4 · First 30 days

Roy joins the leadership meeting starting week one. First prototype is in motion by day five. By day fourteen, the vendor landscape memo for your priority decision is on your desk. By day thirty, the AI roadmap for the next two quarters is locked, with the hiring plan attached. You get back the Thursday afternoons.

Step 03

Month 2 onward · Steady-state cadence

Predictable weekly rhythm. Monday leadership meeting, midweek engineering session, Friday memo or vendor call. Monthly executive review with your CEO and CTO. Quarterly board-ready AI section for your investor update. Roy is reachable on Slack between cadences for fast calls when something breaks.

// What hands-on means

A consultant writes a deck. A fractional CAIO ships.

The category most founders have seen is the AI consultancy that arrives with a slide team, runs interviews for two weeks, produces a 60-page strategic recommendation, invoices, and leaves. The deck is usually correct in the abstract. It is also rarely actionable inside a 35-person team that has three sprints and one engineer to spare. The strategy and the execution sit in different rooms. By the time your team translates the deck into a roadmap, the landscape has moved.

Hands-on means the opposite of that. Roy is in your repo, in your eval harness, in the room when a model choice is being argued. When the team needs a working agent prototype to show a customer next Tuesday, the fractional CAIO is the person who builds it with your engineers, not the person who briefs them and waits. Code reviews on AI-heavy PRs. Real model evaluation runs, not gut calls. Vendor demos taken in the same week they get requested.

The deliverable on a fractional CAIO engagement is not pages of analysis. It is decisions made, prototypes shipped, vendors selected, hires made, and a team that knows what they are building next month. The memos that do get written are short and load-bearing. Two pages on a build-vs-buy call. Three pages on the agent architecture for the priority workflow. Strategy as a byproduct of shipping, not a substitute for it.

For a deeper read on how the wider EOI department model layers under this, the AI Sales Department and AI Ops Department pages walk through how the fractional CAIO engagement maps to underlying execution capacity when you want both strategy and operating teams from the same operator.

// The founder-time math

Six hours back every week is a different company.

A founder running a Series A or Series B team without a CAIO typically gives up 6 to 10 hours a week to AI strategy work they cannot fully resolve. Vendor calls that should not be on their calendar. Slack threads about model choice. Reading research papers at 11pm. Writing the AI section of the board update from scratch. Standing in for the CAIO in product reviews. None of these tasks alone is a crisis. Collectively, they cost a quarter of the founders week.

Reclaim that quarter and the company changes shape. The founder spends more time with customers, more time recruiting, more time on the things only a founder can do. The team gets a sharper AI roadmap because somebody whose entire job is thinking about it owns the answer. The board gets cleaner narrative, which compounds into the next round. The cost of the fractional CAIO is recovered in founder-time alone, before any of the prototype or vendor work shows up in the P&L.

For founders who want to validate the scope before committing to a retainer, the AI Strategy Audit is the one-time on-ramp. Two weeks, fixed price, working artifact and roadmap at the end. Many fractional CAIO engagements start as a strategy audit and convert when the founder sees what the next quarter of work would look like.

Excellent communication and top-notch quality of service. EOI has been a choice to accelerate our company, not only on a technical level, but also business-wise and creatively. If you need anyone to do your AI workflows, these guys are the experts.
Gregory Benjamins
CEO · Green Collective
// Pricing

Monthly retainer. No equity, no long lock-in.

Monthly retainer · 60-day minimum

A fraction of a loaded CAIO salary, no equity grant, no recruiting fees. Cancel any time after the first 60 days.

  • Standing seat in your weekly leadership meeting
  • 32 to 48 hours per month of executive + hands-on time
  • Hands-on prototype work in your repo with your engineers
  • Monthly strategic memos and quarterly board-ready AI section
  • Vendor evaluation, decision memos, and selection ownership
  • Hiring panel participation for AI engineering and leadership roles
  • Fractional CAIO title and email if useful for investor or customer credibility
  • Direct Slack line to Roy between scheduled cadences
Book a scoping call
// Not ready for a retainer yet

If you want to validate the scope before committing to a monthly engagement, the AI Strategy Audit is a two-week, fixed-price on-ramp. You get a written roadmap, a vendor landscape memo, and a working prototype. Many fractional CAIO engagements start here.

See the strategy audit
// FAQ

The questions founders ask before they apply.

01What hours and how is the time spent?
Typically 32 to 48 hours per month, averaging eight to twelve hours a week. A standing leadership meeting, one or two engineering sessions, vendor calls, a monthly memo. Time is tracked at the cadence level rather than the hour. Roy is reachable on Slack between cadences for fast calls.
02Can we use a fractional CAIO title on our deck and website?
Yes, by default. The retainer includes a fractional Chief AI Officer title and an email on your domain if it helps with investor or customer credibility. Roy is comfortable being introduced this way to your board, customers, and recruits, with the fractional nature disclosed where it matters.
03Do you work alongside our existing CTO or CPO?
That is the default shape. The fractional CAIO does not replace your CTO or CPO. Roy sits beside them in leadership meetings, owns the AI roadmap specifically, and keeps coordination clean. The role works best when the CTO owns engineering broadly and the CAIO owns AI direction, with overlap on AI engineering hires.
04What does the first month of the engagement look like?
Week one: scoping memo finalized, leadership meeting seat starts. Week two: first prototype in motion, vendor landscape memo on priority decision. Week three: AI hiring plan drafted, build-vs-buy memo on top architectural call. Week four: two-quarter roadmap locked, monthly review with CEO and CTO. Concrete output every week.
05Do you take board observer seats?
Occasionally, by mutual agreement. For most engagements the work is captured in the weekly leadership meeting and a quarterly board-ready memo, which is sufficient. Board observer seats are available for retainers above a higher tier and where it materially improves the work. Decided case by case.
06How do you handle confidentiality and conflicts of interest?
Standard mutual NDA at engagement start, plus a written conflict policy. Roy does not take fractional CAIO engagements with two direct competitors at the same time. Client list is disclosed at scoping. EOI department engagements with non-competing companies in adjacent verticals are fine and surfaced upfront.
07Can the engagement scale up to interim full-time if we need it?
Yes, for short defined windows. If a fundraise, acquisition, or product launch needs interim full-time CAIO presence for four to eight weeks, we can scale the retainer accordingly. Roy does not take permanent full-time roles, but interim surge is part of how the engagement flexes for funded teams.
08How do you measure success on a fractional CAIO engagement?
Three concrete outputs per quarter: a locked AI roadmap, shipped prototypes against the roadmap, and decisions made on vendor and hiring fronts. Plus founder-time freed, tracked subjectively at the start and revisited at month three. If the roadmap is not sharper and the founder is not getting hours back, the engagement is not working.
// From the notes
// Also worth a look
// Ready to ship this?

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