Fractional CTO Services

A CTO for the months before you hire one

You have software in production and nobody senior to make the technical calls: which vendor, whether to rebuild, what to do about the contractor who went quiet. I make those calls with you, by the month, until you're ready to hire a full-time CTO.
From $5,000/month, month to month. Serving startups and SMBs across Tampa, Orlando, Lakeland, and Central Florida, and remote everywhere else.

What you get

The parts of a CTO's job a small company actually needs, priced by the month.
01

Technology strategy

A roadmap tied to revenue, a stack you can hire for, and a written answer to "should we build this?"

02

Architecture reviews

Find what breaks at ten times the load before your customers do, and fix the parts that matter.

03

Hiring and mentoring

Write the job description, run the technical interview, and review code so your developers get better on purpose.

04

Vendor calls

Straight recommendations on tools, platforms, and dev shops. No reseller deals, so nothing to steer you toward.

05

Security and compliance

Auth, secrets, backups, and access reviewed against what your customers and auditors will ask about.

06

Technical due diligence

Raising or selling? Get a written assessment of your code and infrastructure before the buyer's engineer writes one for you.

It usually starts with one of these

A call you can't make alone

Rebuild or refactor. Which vendor. A developer or a dev shop. Decisions that are expensive to reverse and hard to make without someone who has made them before.

A contractor gone sideways

Missed dates, vague updates, code nobody else can read. You need someone to look at it and tell you what's true.

A question from the board

An investor asked about security, scale, or tech debt, and you didn't have an answer you trusted.

Not sure if you need a full-time CTO instead?

I wrote an honest, no-strawman comparison of when fractional wins and when it's time to hire full-time.

Compare fractional CTO vs. full-time CTO

Building an AI product and need shipping, not just leadership?

A forward deployed engineer sits inside your team and ships agents, integrations, and evals. It's a different job from leadership, and often the one AI teams need first.

See forward deployed engineer
Matt has been an invaluable partner as a fractional CTO — leading complex CRM integrations, building custom programs that enhanced our operational efficiency, and contributing to cost-saving initiatives that positively impacted our bottom line. He's incredibly reliable, often available around the clock, and genuinely cares about delivering results.
Tim Madden
CEO & Founder, Executive Career Upgrades
FAQ

Frequently Asked Questions

What does a fractional CTO do?

A fractional CTO provides part-time, senior-level technical leadership for your company. This includes setting technology strategy, reviewing architecture decisions, mentoring development teams, evaluating vendors, overseeing security practices, and making CTO-level decisions — without the cost of a full-time executive hire. My fractional CTO services are tailored to startups and SMBs in the Tampa-Orlando area who need experienced technical guidance.

How much does a fractional CTO cost?

Two month-to-month retainers: Advisor at $5,000/month (two working sessions plus async access) and Embedded at $9,000/month (weekly sessions, your Slack, and hands-on review in your repos). Both are on the AI advisory pricing page at redleg.dev/advisory. A full-time CTO at Series A scale runs $250k+ plus equity; this is the version where you only buy the months you actually need leadership. No annual contract, no termination fee, thirty days' notice either way.

Do I need a fractional CTO or a full-time CTO?

If you're a startup or SMB with a small development team (or no team yet), a fractional CTO is usually the right choice. You get the same strategic guidance and technical oversight without the full-time salary commitment. A full-time CTO makes sense when your engineering team exceeds 15-20 people and you need daily, hands-on leadership. Many of my clients in the Tampa-Orlando corridor start with fractional CTO services and transition to full-time as they scale.

Can a fractional CTO work with my remote team?

Yes. Most engagements are remote. Red Leg Dev is based in Lakeland, Florida, so in-person days in Tampa, Orlando, and the rest of Central Florida are easy when a whiteboard helps.

What industries does Red Leg Dev serve as a fractional CTO?

I have fractional CTO experience across banking and financial services, healthcare, automotive technology, SaaS startups, payroll processing, construction, credit unions, and education. With 15+ years of SaaS and product development experience, I adapt quickly to your industry's specific requirements and compliance needs.

Serving the Tampa–Orlando Corridor

Based in Lakeland, Florida, I provide fractional CTO services to businesses across Central Florida — including Tampa, Orlando, Brandon, Plant City, Winter Haven, and Kissimmee. I work both in-person and remotely.
Tampa, FLOrlando, FLLakeland, FLBrandon, FLPlant City, FLWinter Haven, FLKissimmee, FL

Get the next big call right

Thirty minutes, free. Bring the decision you're stuck on. You'll leave with a recommendation, whether or not you hire me.
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