ENTERPRISE AI ARCHITECTURE · FRACTIONAL CTO · COLORADO SPRINGS

Forty years of building what has to work. Now applied to enterprise AI.

Autonomous agent workflows, zero-trust data pipelines, and core system modernization — led by a veteran founder who has shipped mission-critical software for decades. Board-ready fractional CTO & AI advisory.

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

The enterprise reality check

Why most corporate AI pilots never reach production.

The Trust Gap

Moving past simple chatbots requires graduated autonomy and deterministic guardrails, so agents never fail unpredictably in production.

The Token Cost Explosion

93% of surveyed enterprises exceeded their AI budgets as pilots reached production (McKinsey, May 2026). The fix is designed in, not bolted on: route routine calls to small models — 10–30× cheaper to serve, per NVIDIA's benchmarks.

The Hidden Data Debt

AI is only as good as the data beneath it. Core systems must be modernized to feed clean, real-time context to models — safely.

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.

The real barrier to enterprise AI is legacy data hygiene and compliance — the same challenges solved in billion-dollar core migrations.

$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.

Mission-critical reliability: zero-error tolerance is built into the architecture from day one — the standard your AI stack deserves.

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

Core framework capabilities

The architectural playbook behind every engagement.

01

Agentic Workflows

Deterministic multi-agent state machines (LangGraph and similar) with built-in human-in-the-loop checkpoints for regulated industries.

02

Zero-Trust Pipelines

Secure streaming pipelines that scrub PII and enforce strict memory boundaries before data ever reaches a commercial LLM gateway.

03

Core Modernization

Bridging decades-old databases, CRMs, and mainframes to modern vector stores through clean, unified API standards.

Service offerings

Enterprise AI, scoped and priced like enterprise software.

01

Discovery & Technical Blueprint

$5k–$15k

A two-week architectural assessment of your legacy schemas, security boundaries, and highest-friction workflows. Delivers a production-ready agent architecture, a security roadmap, and an ROI model.

02

Autonomous Agent & Pipeline Implementation

$25k–$150k+

Production RAG, semantic middleware, automated PII scrubbing, and multi-agent workflows with human-in-the-loop controls — engineered to the zero-downtime standard your core systems already demand.

03

Fractional CTO & Managed AI Retainer

$5k–$10k/mo

Executive leadership, FinOps and token-cost governance, model drift monitoring, architecture reviews, and engineering team guidance. A season of ownership, not a dependency.

Randy Fair

About Randy

"Your user experience should be exciting.  Your infrastructure should be boring.  I build both."

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

Move from AI experimentation to production alignment.

Book a Fractional AI Strategy Session. I'll analyze your manual system bottlenecks and deliver an initial high-level architectural roadmap that moves you safely past the pilot phase.