27 Years of Watching Things Blow Up
I've spent my career building software at every scale. More importantly, I've seen every way these decisions go wrong.
Where I've Worked
- Fortune 500s: Where process matters and scale kills you. I've seen enterprise teams move so slow they got eaten by competitors.
- Startups: Where speed beats perfection and tech debt is a feature. I've seen companies scale their architecture before finding customers.
- Military: Where security isn't optional and downtime costs lives.
- Hedge funds: Where correctness under pressure is everything.
- SaaS: Where uptime is revenue and outages are existential. I built and sold a SaaS. Still run production systems.
I've rescued teams from every expensive mistake. So you can avoid them.
What I've Seen Fail
$50M rewrites that never shipped.
Teams paralyzed by "senior" hires who made everything worse.
Startups that scaled their architecture before finding customers.
Enterprises that moved so slow they got eaten by competitors.
Solo founders who built fast with AI but had no idea what was about to break.
The Quick Version
Founder with one exit. SaaS operator who understands both product and sales. Currently run Backup Parachute Software.
27+ years delivering software for Fortune 500s, hedge funds, government agencies, and fast-moving startups.
Fractional CTO trusted by growing companies to steer technical decisions that actually move revenue.
I help dev teams ship what customers actually need, not just what they asked for.
27 years is not worth much on its own. What it buys is pattern recognition. The frameworks change every few years. The mistakes don't. The rewrite that never ships, the senior hire who isn't, the architecture built for customers you don't have yet. I have watched each of those play out enough times to spot them early, when they are still cheap to fix.
I don't have all the answers. But I've probably seen your situation before.
More about Kyle at kylemiller.com