John Fly III, DSL

Chief Technology Officer at FirmPilot

Readyville, Tennessee, United States

About John Fly III, DSL

John Fly III, DSL is Chief Technology Officer at FirmPilot. Location: Readyville, Tennessee, United States.

I build what a company can't build for itself, and I fix what everyone else has given up on. For 30 years, at every size of company, the pattern has held: I run at the hardest, most-avoided problem in the building and leave behind a system that works, scales, and lasts. It started at fifteen, cold-calling my way into a programming job and helping a six-person company out-build competitors twenty times its size. A small team wins on what it is willing to build, not its headcount. Selected results, across startups, scale-ups, and public companies: - FirmPilot (current, AI legal-marketing): built the AI platform from nothing to 100+ law firms and helped raise more than $27M from Thomson Reuters Ventures and HubSpot Ventures, at a $100M valuation. - Legacy (digital health, Series B): cut average work-in-progress age from six months to under one, moved delivery from the slowest tier to the fastest, and reached SOC 2 readiness in three months. - SmileDirectClub (NASDAQ, consumer health): took a mobile program every other leader had written off, a year behind, to a production beta in three months, and grew the team from 9 to 30+. - WebMD (healthcare transactions): self-taught a mainframe nobody would touch and cut its compute 30 to 60%, results so unusual finance opened an inquiry into the savings. - RANDA (edtech): invented, unasked, the workflow engine that became the flagship product, on systems that scaled to 300,000 users and 150,000 concurrent. My turnarounds are engineering and execution turnarounds, not clean-up jobs. I tear out broken operating models and rebuild how teams ship, moving teams from the slowest delivery tier to the fastest. Away from the keyboard I build and restore things by hand, and I bring the same instinct to systems: build holistically, to tolerance, and don't stop until it works and lasts. What most people call impossible is usually just hard work that most people won't do. I code the first version, build the team that scales it, and can explain to a board exactly why it works. I build across the whole organization, not one slice of it. I hold a Doctor of Strategic Leadership and publish peer-reviewed work on feedback loops and AI governance. Focus: AI-native platforms, agentic systems, platform builds and modernization, engineering turnarounds, enterprise architecture, and technology leadership at scale.

Skills

  • AI Strategy
  • C Level Management
  • C Suite

Additional experience

  • Ambassador, Gartner Peer Community

    Gartner

    Started July 2023

Education

  • Doctor of Strategic Leadership, Liberty University
  • Master of Business Administration (MBA), Bottega University