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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

The early technical decisions are the ones that come back to haunt you.

A wrong architecture bet, a mis-timed hire, six months building something nobody wanted. These are the mistakes that surface months later, when they’re expensive to undo. I’ve seen what breaks at scale, and I can tell you 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 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.