Fractional CTO · Colorado Springs

Forty years of building what has to work.

Enterprise systems, mergers, and regulated platforms — led by a founder who has shipped them since before the cloud. Retainer-grade CTO leadership, no full-time hire.

40

Years in software

50+

Apps delivered

99+

Projects led

30+

Airports served

J.P. Morgan ChaseCIAL3HarrisUSADAWings Credit UnionSwiss OlympicBank of AmericaDFW AirportWADAWillis Towers Watson

Selected work

01

The second-largest credit union merger in history

Directed four agile engineering teams through the full core-banking integration, then architected the $243M asset-securitization loan migration — zero customer-facing downtime.

$243M migration · 4 teams

02

Air traffic control at the world's busiest airports

Flight and operations tracking systems still running today across 30+ major hubs — DEN, DFW, LAX, JFK — where a single defect is not an option.

30+ airports · safety-critical

03

An anti-doping platform, sold to WADA

Built the USADA data warehouse and dashboard, then led the sale of the platform to the World Anti-Doping Agency and the Swiss Olympic Committee.

USADA → WADA exit

04

Two decades of DewEye consultancy

A founder-led practice delivering 50+ enterprise applications for banking, aviation, investment, and government clients — L3Harris, Willis Towers Watson, Port Authority NY/NJ.

20+ years · founder

How an engagement runs

Leadership you can dial in — then hand off.

01

Diagnose

A focused read on your architecture, team, and the decisions quietly blocking you — where the risk actually lives and what it costs to leave it there.

02

Build & lead

Hands-on engineering leadership embedded with your teams — hiring, roadmaps, vendor calls, board decks, and the hard calls a CTO should carry.

03

Hand off

Documentation, a trained internal owner, and a clean exit. The retainer is a season, not a dependency.

Randy Fair

About Randy

"The best systems are boring. I like boring."

Randy started coding on a Commodore 64 at fifteen, served as a Computer and Telecommunications Specialist in the US Air Force, and has spent four decades since building software that carries consequences — for the CIA, the FAA, J.P. Morgan Chase, and credit unions worth billions. He founded and ran his own consultancy for twenty years, and along the way a coffee lounge with a team of twenty. Father of ten, husband of one, and a firm believer that the best architecture reviews happen over a very good cup of coffee.

Let's talk

Bring me the hard problem.

Board-ready, hands-on, and honest about what a retainer can and can't fix.