You don't just get a chief AI officer. You get the whole machine.
Every Fractional AI CTO engagement comes with two things most firms can't buy separately: a senior AI executive who's shipped this in insurance, finance, and fintech, and the Keep, our private AI operations system, installed for your business and run for you 24/7. Strategy at the top. A system underneath doing the work. One engagement, everything included.
Related reading: The Keep, the system inside · What is a fractional AI CTO? · AI for insurance · How we build
Digital Monestary is an engineer-led agency. The Fractional AI CTO seat is led by our founder, Josh Cruz: 12+ years building and shipping production systems, teams of 25+ engineers led, fintech platforms architected from scratch, and AI put into production under real governance. Agentic workflows, SOC 2 sign-off, human-in-the-loop. Not slide decks. Shipped systems with real results.
You see the AI opportunity. Every call still feels like a gamble.
What to build, what to skip, how to keep client data safe, how to get a team of producers or advisors to actually use any of it. A full-time CTO to own those calls runs $250K to $450K a year, takes six months to find, and still needs a team and infrastructure behind them. This engagement replaces that entire stack. One flat monthly engagement, live in about two weeks, cancel with 30 days notice.
- ◆A senior partner, not a vendor dropping off tools and disappearing.
- ◆You stop guessing on the big AI bets. Someone who's shipped this owns the call.
- ◆Your team actually adopts AI, instead of buying software that sits unused.
- ◆Your data stays safe, handled the way few agencies bother to.
- ◆You can stop any month. Part-time, fully remote, never locked in.
One engagement. Six things you'd otherwise buy separately.
The Abbot: your chief AI officer
Senior AI leadership in the room. The roadmap, the build-or-skip calls, the vendor decisions, a seat at your leadership table. Led personally by our founder, who's spent 12+ years shipping production systems and leading teams of 25+ engineers.
The Keep: your AI operations system, installed
The part nobody else includes. We install a private, always-on system built for your business, and your operations start running on it. Follow-ups at 9pm. Intake parsed before the coffee's on. Reports that show up finished. It runs while your team sleeps, and we run it so your team never has to. Full breakdown of the Keep →
Hands-on engineering
We don't hand you a slide deck and a to-do list. We build the systems, engineer-led: real code, shipped and maintained. Your headcount stays flat while your output doesn't.
The Rule: governance built for regulated work
A human approves anything sensitive. Deterministic, testable code makes the decisions on regulated sends, not a language model's best guess. SOC 2 discipline on every change. Your compliance person gets real answers, fast.
The Chronicle: the receipts
Every action your systems take, logged and readable. What ran, when, why, and who approved it. When a regulator, an E&O carrier, or your own board asks, the answer takes minutes.
Team adoption
AI only pays when people use it. We train your team, build the daily habits, and stay until it sticks.
What this replaces.
Hiring this capability yourself looks like a full-time CTO or chief AI officer at $250K to $450K, an automation engineer at $150K+, plus the infrastructure, tooling, and governance work on top. Call it half a million a year, and six to twelve months before anything ships.
The results compound, because the Keep keeps running. The system we ship in month one is still working in month twelve, with eleven more stacked on top of it.
Roughly a third of one senior hire, for the executive, the engineering, and the running system together.
- ◆No equity, no benefits, no executive search
- ◆Live in about two weeks
- ◆Month-to-month, 30-day exit, never locked in
The kind of results this seat delivers.
Real results our founder has delivered, described by industry rather than client name. Your numbers depend on your business, and we'll tell you honestly what's realistic before you spend a dollar.
A tangled pipeline was quietly killing good deals.
Tangled backend data, stale leads, no clear view of what to work next. Good opportunities were quietly dying.
Clean modular pipeline tools, automated lead enrichment, and a smart engine that retires stale leads on its own.
Manual processes were costing thousands of hours a year.
Core processes run by hand: slow, error-prone, impossible to scale.
Custom dashboards and step-by-step automation that took over the manual work and doubled processing speed.
Complex partner payouts, all done by hand.
Multi-party revenue splits across white-label partners nobody wanted to calculate manually.
Architected the platform from scratch with an autonomous multi-tier billing engine on Stripe Connect.
Costly downtime and a platform at its limits.
Expensive equipment downtime while the system bumped against processing ceilings.
An AI-driven fix plus a re-architected data layer customers can extend without code.
We'd rather show than tell: on your strategy call, ask us to open live systems running in the Keep right now, logs and all.
Your options for senior AI leadership.
What you're probably wondering.
What exactly is the Keep?
Is it just advice, or do you build too?
How is a Fractional AI CTO different from hiring a full-time CTO?
Do you work on-site?
What does it cost, and can we stop?
How fast can we start?
What happens if we part ways?
Can you work with my existing team and tools?
Stop making the big AI calls alone.
Tell us where you want the business to go. We'll tell you honestly what's worth building, in what order, and then we'll build it and run it. Worst case, you leave the call with a straight answer about what AI can and can't do for your firm. Best case, you get the department without the payroll.
Book a strategy call →