Skip to content
Cindy Don

Fractional CTO · AI-native engineering

Build better.
Ship faster.
Scale leaner.

You bring the vision and the domain expertise. I bring twenty years of shipping product, as a hands-on fractional CTO who’s led at the executive level and still builds with AI.

  • A roadmap aimed straight at product-market fit
  • An AI workflow that accelerates your team strategically
  • Architecture that won't need a rewrite in a year
Cindy Don

Most startups don't need a full-time CTO. They need the right calls, made early.

The wrong architecture, a mis-timed hire, six months spent building the wrong thing. The early technical decisions are the expensive ones to get wrong. What you need is someone who’s seen what breaks at scale and can tell what actually matters on the path to product-market fit.

And the way software gets built has changed. I build AI-native workflows around your actual team, not a template, so development gets genuinely fast. But the real win isn’t speed. It’s that you learn what the market wants faster, and I know how to turn that into the right calls instead of just more code.

The result: a small team that ships like a much bigger one.

Core services

Four ways I help you build better and ship faster

Tech + Security Assessment

When you need a clear read before a big technology, product, or hiring decision.

  • The real reason execution is slow, not just the symptoms
  • Architecture and engineering org review
  • Product delivery and technical debt check
  • Where AI gives you real leverage, and where it won't
  • Technology and security risk review
  • A 90-day roadmap you can act on Monday

Fractional CTO Leadership

When you need senior technical leadership without the full-time price tag.

  • Executive technology decisions across product, engineering, and AI
  • Roadmap prioritization and where your engineering dollars go
  • A healthy product and engineering operating rhythm
  • Hiring: who, when, and how to actually interview them
  • Board and investor support when the technical questions come
  • Scaling output without ballooning the team

Build and Ship

When you need something shipped, not another strategy deck.

  • I own the path from roadmap to working software
  • Turn your prototype into something that survives real users
  • An AI-native way of working, built around your team
  • Product, engineering, and ops pulling the same direction
  • Tight build, test, learn loops so you stop guessing

Technical Due Diligence

When you or your investors need an honest read on technical risk.

  • Product and execution maturity
  • AI readiness, and where the technical risk is hiding
  • Architecture and scalability review
  • Engineering team and org assessment
  • A plain-English summary with an investment recommendation

Proven results

Twenty years across fintech, insurtech, climate tech, and e-discovery — and a consistent pattern of pairing systematic execution with AI to move teams further, faster.

Lower dev costs
75%Lower dev costsvia AI transformation at Pangea
Faster delivery
Faster deliverygoal-driven squads + Claude agents
Uptime
99.9%Uptimeup from 90% at Jellyvision
CO₂ removed
200K tCO₂ removedproducts shipped at Nautilus Labs

Real transformation stories

From an AI-native overhaul at a money-transfer platform to a climate-tech scale to acquisition, the pattern holds: build systematic execution and AI capability together, and lean teams start punching well above their weight.

  • Pangea: AI-native transformation
  • Nautilus Labs → acquired by Danelec
  • Jellyvision: 90% → 99.9% uptime
Cindy Don speaking on a panel at 1871 in Chicago

Hi, I'm Cindy.

I’ve spent 20+ years building software and leading engineering teams across finance, insurance, climate, legal, and healthcare. I’ve tripled delivery speed, taken platforms from 90% to 99.9% uptime, helped a startup scale to acquisition, and shipped products that removed 200,000 metric tons of CO₂ from the atmosphere.

These days I’m a hands-on fractional CTO for early-stage founders, productionizing prototypes and shaping the technical strategy that gets them to product-market fit and funded. I stay hands-on on purpose: I’m also building a social impact app with AI as my development partner, so my advice comes from how AI-native development actually works, not how it’s marketed.

I care most about technology that solves real problems for real people. If that’s what you’re building and you want a hands-on technical partner who’ll give you a straight answer, let’s talk.

Ready to build better?

If your prototype needs to become real, your roadmap needs a point of view, or you want a customized AI strategy for your team and product, let’s talk. No pitch, just a straight read on what it would take.