Fractional CTO and technical leadership

Grow the business on the software you already have.

Whether an agency built it, your CTO just left, or investors are about to look under the hood, in two weeks we’ll tell you plainly where it stands and what to do next. Then we stay on your side to get it done.

We’ve kept a live insurance platform moving through federal audits, acquisitions, and a switch to B2B sales, and helped a fintech grow through $49 million in funding without a rebuild.

Sound familiar?

  • “Our CTO just left.”

  • “The agency says it’s fine. Is it?”

  • “I don’t know if our developers are any good.”

  • “We got a quote to rebuild it. Do we really need to?”

  • “Investors are about to look under the hood.”

Whatever the situation, you need one senior person on your side who will give you a straight answer and take responsibility for fixing it. We work for you, not the vendor.

How we start

Technical Second Opinion

Two weeks. Fixed fee. A clear answer on where your software stands and what to do next.

  • What we look at

    The code and architecture, security basics, hosting and accounts (who has access to what), the team or vendor building it, and what depends on one person.

  • What you get

    A plain-English report, a prioritized fix list any engineer could pick up, a 90-day plan, and a 60-minute readout with you.

  • Our promise

    The report stands on its own whether or not you keep working with us. We don’t sell rebuilds.

Fixed fee, agreed before we start.

Then: your fractional technical lead

If it makes sense, a senior Stackpad engineer stays on as your technical lead for a few hours a week. Some people call this a fractional CTO.

  • Hands-on, not just advice. We work in your codebase and with your team or vendor.
  • One defined result in three months. For example: releases shipping again, the vendor under control, the platform ready for diligence, or your permanent technical leader hired.
  • Six to ten hours a week, as a three-month pilot you can end monthly.

When the work grows

If there’s real work to do after the report, our senior team can take it on, or we’ll help you hire the people who can. We’ll always tell you if someone else is a better fit.

Work

Two companies that grew on the software they already had. It’s the same job we’d do for you.

Catch

Health insurance for the self-employed

When Catch was acquired in 2023, our in-house roles became Stackpad’s first client. Since then we’ve owned Catch’s technology through its biggest business moves: federal audits that keep it approved to enroll customers, acquisitions, and this year, CMS approval for an agent and broker pathway that moved Catch from selling direct to consumers to selling through agents and brokers.

Read the Catch case study
Lettuce

The business behind the business for the self-employed

Part of Lettuce’s engineering team since day one, as it grew from tax automation into banking, payroll, an AI assistant, and health benefits, and raised $49 million. Every new product went onto the same platform without a rebuild, and it held up through every tax-season peak.

Read the Lettuce case study

Who we are

Stackpad was founded by senior engineers who’ve carried companies through audits, acquisitions, and new ways to sell. No junior consultants with senior titles.

  • Matt Little, Co-founder

  • Lexi Smith, Co-founder

Meet the founders →

Questions

Is this a fractional CTO?
In practice, yes: a senior technical lead for part of the week. We start with a two-week Technical Second Opinion so you see how we work before committing to more.
What if our software is fine?
Then we’ll tell you, and the report will say so. A clean bill of health is a good outcome.
Will you replace our agency or developers?
Only if that’s the right call, and the report will lay out the options, including ones that don’t involve us. We often work alongside the team you have.
Will our agency or developers know?
That’s your call. It’s usually simplest to tell them it’s a standard review, and we work with them professionally. The goal is a clear picture, not blame.
What if it needs fixing?
The report lays out your options, including ones that don’t involve us: your current team with clearer direction, a new hire, or Stackpad.
What do you need from us?
Read access to the code and hosting, an hour with whoever builds it, and an hour with you.
How soon can you start?
We take on a small number of clients at a time. Book a call and we’ll tell you honestly when we can begin.

Not sure your software can carry what’s next?

In 30 minutes we’ll ask the questions a good technical lead would ask and tell you plainly what we’d look at first. No pitch deck.