Fractional AI CTO · "The Abbot"

You're making big AI decisions — with no one senior in your corner.

Senior AI strategy, hands-on engineering, and real governance — part-time, fully remote. We set the roadmap, build the systems, get your team actually using AI, and keep your data safe. All of it for about a third of a full-time hire. From $10,000/mo.

Related reading: What is a fractional AI CTO? · AI for insurance · AI for RIAs · How we build

Josh Cruz, founder and CTO of Digital Monestary
Led by Josh Cruz
Founder · CTO · Applied AI Engineer · Redding, CA

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.

Who it's for

You see the AI opportunity. Every call still feels like a gamble.

What to build, what to skip, how to keep data safe, how to get your team to actually use it — and how to pay for the judgment to make those calls. A full-time CTO runs $250K–$450K. You need the clarity, not the overhead.

  • You get 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 — security and PII handled the way few agencies bother to.
  • You can stop any month. Part-time, fully remote, never locked in.
What's included

Strategy, builds, adoption, and safety — all of it.

The lower rungs install systems and keep them running. The Fractional AI CTO is different: we help you decide where the business is going, build the systems to get there, and make sure your team actually uses them.

🧭

AI Roadmap

A revenue-tied strategy: what to build, in what order, and why. We anchor every decision to what pays — not what's trending.

🤝

Team Adoption

AI only pays off when people use it. We train your team and build the daily habits so it stays off the shelf and earns its keep.

🛡

Data Safety & Governance

Security, PII handling, and SOC 2 AI governance with human-in-the-loop — the part most agencies skip. You scale without exposing yourself.

📈

Hands-On Builds

We don't just advise — we build. Real code, real systems, shipped. More output from your current team, without adding headcount.

Proven results

What senior AI leadership actually delivers.

Real results our founder has delivered — across insurance, equipment finance, fintech, and manufacturing. Described by industry, not by client name.

Insurance · enterprise sales

A tangled pipeline was quietly killing good deals.

The problem

Tangled backend data, stale leads, no clear view of what to work next. Good opportunities were quietly dying.

What we built

Clean modular pipeline tools, automated lead enrichment, and a smart engine that retires stale leads on its own.

$1.7M
in added sales revenue, with pipelines that manage themselves
Equipment finance · operations

Manual processes were costing thousands of hours a year.

The problem

Core processes run by hand — slow, error-prone, impossible to scale.

What we built

Custom dashboards and step-by-step automation that took over the manual work and doubled processing speed.

2,200+
hours saved in one department · 2× faster · ~$450K/yr
Fintech · alternative investments

Complex partner payouts, all done by hand.

The problem

Multi-party revenue splits across white-label partners nobody wanted to calculate manually.

What we built

Architected the platform from scratch with an autonomous multi-tier billing engine on Stripe Connect.

100%
automated payouts across multiple partner brands
Manufacturing · software

Costly downtime and a platform at its limits.

The problem

Expensive equipment downtime while the system bumped against processing ceilings.

What we built

An AI-driven fix plus a re-architected data layer customers can extend without code.

10×
event-processing capacity, re-architected
What it costs — and saves

Senior AI leadership at a fraction of the hire.

A full-time CTO runs $250K–$450K a year — before equity or benefits. A fractional engagement puts that same level of judgment on your team, scoped to what you actually need, with a 30-day exit whenever you want it.

from $10,000 /mo

Scoped to the hours and work you actually need.

  • ~⅓ the cost of a full-time CTO
  • No equity, no benefits, no long-term commitment
  • Month-to-month — 30-day exit, never locked in
  • Live in ~2 weeks, not a 4–6 month executive search
FAQ

What you're probably wondering.

How is a Fractional AI CTO different from hiring a full-time CTO?
You get senior AI leadership — strategy, hands-on builds, and someone to own the technical calls — part-time and fully remote, for about a third of the $250K–$450K a full-time CTO costs. No equity, no benefits, and you can stop any month.
Is it just advice, or do you build too?
Both. We set the roadmap and we build it — real systems and real code, not slide decks. We also lead your team and your vendors, and handle AI governance so things ship safely.
Do you work on-site?
No — engagements are fully remote. We work as part of your team over the tools you already use, so location is never a constraint.
What does it cost, and can we stop?
Engagements start at $10,000/mo, scoped to the hours and work you actually need. It's month-to-month with a 30-day exit — you're never locked in.
How fast can we start?
Most engagements are live in about two weeks, not the four-to-six months a full-time executive search takes.
What results have you delivered?
Results our founder has delivered include $1.7M in added sales revenue from pipeline automation for an insurance brokerage, 2,200+ staff hours saved and roughly $450K/year in efficiency for an equipment-finance lender, and 10× event-processing capacity for a manufacturing software platform. We describe work by industry, not by client name.
Can you work with my existing team and tools?
Yes. We join your team and work over the tools you already use. A big part of the role is helping your people actually adopt AI — and leading your vendors — not ripping out what already works.
Ready when you are

Stop making big AI calls alone.

Tell us where you want to take the business. We'll tell you honestly what's worth building, in what order — then build it with you.

Book a strategy call →