Fractional CTO

You run the business. We’ll run the technology behind it.

One senior person runs your roadmap, your vendors, and your technology decisions — with a plan you can follow and a scoreboard you can read in two minutes.

From $8,000 a month · 3-month minimum

A captain in a waistcoat steering a brass ship's wheel
Years running business systems
13+
To a full Systems Map
30 days
Max response time
1 day
Openings for Q1 2027
2

Why owners call us

You are likely here because…

  • “I don’t know what I don’t know.”

    Within 30 days you have a clear map of your systems, risks, and gaps — on one page.

  • “Every vendor is selling me something.”

    Someone on your side vets them, negotiates, and says no when the answer is no.

  • “Tech projects drag and I can’t tell if they’re on track.”

    Every initiative has an owner, a date, and a status you can read in two minutes.

  • One Owner

    Roadmap, vendors, architecture, and priorities sit with one senior person — not with you by default.

  • Senior Judgment

    Executive-level technology decisions from someone who has made them before, scoped to what your business needs.

Power Techniques Inc. case study Power Techniques Inc. Field operations connected from site to office

Who it's for

Growing businesses with no one owning technology.

Usually $3M–$50M in revenue, adding customers, people, sites, or acquisitions faster than the systems can keep up. Technology decisions get made reactively — by the owner or the ops team — because nobody owns the whole picture.

Clara fine-tunes a winged mechanical assistant.

WHAT YOU GET

What you get, and when.

FIRST 30 DAYS

Systems Map and 90-day plan

Every system, vendor, risk, and gap on one page, plus the first quarter's priorities.

Your first month, done

EVERY FRIDAY

Written update

The scoreboard, what moved, what's blocked, what we need from you. Two minutes to read.

13× per quarter

EVERY TWO WEEKS

60-minute working session

Decisions, priorities, vendor and project review with you or your leadership team.

6× per quarter

EVERY QUARTER

Half-day strategic review

The plan and scoreboard reset for the next 90 days. In person where practical.

1× per quarter

Always on

  • Decision log

    Every technology decision in plain English, with the reason and the date.

  • Direct access

    Email or message, answered within one business day.

WHAT'S IN THE RETAINER

Decisions, direction, and accountability.

Anything that ships code, fixes a device, or takes on-call responsibility is priced separately.

Included

  • Technology roadmap and 90-day plans
  • Architecture and build-vs-buy decisions
  • Vendor selection, negotiation, oversight, and replacement
  • Hiring input: job descriptions, interviews, contractor evaluation. You make the employment call
  • Security posture review and priorities
  • AI adoption: what to use, what to avoid, and the guardrails
  • Specs and requirements for any build, whoever builds it
  • Growth Care for products we built: monitoring, P1 response, and 15 retained hours / month

Not included

  • Building software — quoted separately as Design & Build
  • Support for other live systems — that's Application Care, with its own response times
  • IT helpdesk work: laptops, passwords, email admin. We'll help you pick a managed IT provider, then manage them
  • 24/7 or emergency response, or managing your staff day to day
  • Extra retained hours, hourly rates, or overage billing beyond your Growth Care plan

Transparent plans

Two ways to start.

A monthly retainer when you're ready to hand over the technology picture, or a two-week diagnostic if you'd rather see the map first.

Fractional CTO Retainer

From $8,000 / mo

  • 3-month minimum, then month to month
  • 30 days' written notice, any time after month two
  • Starts within two weeks of signing; first month prorated
  • Billed monthly in advance on the 1st
  • Your rate is locked for the first six months
  • Includes Growth Care for products we built

Not sure yet?

Start with a Technology Diagnostic

$7,500 · two weeks

We interview you and your key people, inventory your systems and vendors, and run a four-hour working session with your leadership team. You get your Systems Map, a punch list of immediate fixes, your risks and blind spots, and a 90-day plan — with a plain recommendation: a fractional CTO, a build, or a plan you run yourselves.

If you go on to a retainer, your first month is already done.

Download the Fractional CTO one-pager (PDF)

WHO YOU'D WORK WITH

One senior person, accountable.

Andrew Smith, founder of Stiff Upper Lip

Andrew Smith

Founder, Stiff Upper Lip

Andrew has led enterprise software architecture for a national multi-unit brand and has spent 13+ years designing and running business systems.

In Andrew's words

Most of the technology problems I get pulled into started as reasonable decisions. A vendor chosen fast because the demo was great or the timeline demanded it. A platform built for 10 users that now carries 10,000. A strong engineering team shipping hard in a direction nobody pressure-tested. By the time it shows up as missed deadlines or a surprise invoice, the cause is often two or three decisions back.

I work on those decisions: platform and tech choices, vendor evaluation and procurement, and building engineering teams that don’t burn out. Much of that is translating between what the business wants and what the technology can do, and making the trade-offs visible to both sides.

Questions I come back to often

  • Should we build or buy?
  • What breaks first when we scale?
  • Is this a technology problem or a team structure problem? (It’s the second one more often than people expect.)

If you're weighing a big technology call or wondering why delivery keeps slipping, send me a message.

Frequently Asked Questions

Finding the Right Fit

Stiff Upper Lip software development team in the office
You also build software. Isn’t that a conflict?

When we recommend a build, we’ll tell you upfront whether we’d like to bid on it. You get the recommendation and the spec in writing before any SUL quote, and you’re free to take that spec to anyone. You own it either way, and when we’re bidding, you make the vendor decision.

What's the minimum commitment?

Three months, then month to month. After month two you can end it any time with 30 days' written notice.

What if something comes up that doesn't fit the cadence?

It becomes a scoped project, quoted separately, or we reprioritize it at the next working session. You never get a surprise invoice for hours.

How is this different from Application Care?

Fractional CTO is direction and accountability: the roadmap, vendors, and decisions. Application Care keeps a live system running, with its own response times. If we built your product and you're on Growth Care, Fractional CTO is the upgrade: the retainer includes your Growth Care plan, and we add the direction on top.

Do you hire people for us?

We write the job descriptions, sit in on interviews, and evaluate contractors. You make the employment call.

How do we get started?

Book a 30-minute strategy call. If you're not sure yet, start with a two-week Technology Diagnostic — if you move to a retainer, your first month is already done.

Can't find the answer you're looking for?

Contact Us

Not the right fit for your current challenge?

Technical leadership comes in many forms. Whether you need a product built, AI woven into your workflows, or a long-term partner in your corner — there's a door for that.

  • Software Design and Build

    You have the idea. You need it built. Discovery through launch, one team — design and engineering together.

  • AI Integration

    Where AI actually fits in your business, built private on our own models — not as a bolt-on demo.

  • Technology Strategy

    Not sure what to build yet — or whether to build at all? We diagnose first, then hand you a roadmap: what to build, what to buy, what to skip.

Ready to stop making technology decisions alone?

One 30-minute conversation to find out what's going on and whether we're the right fit. We take on a small number of fractional clients at a time — two openings for Q1 2027.