Fractional CTO & Rails Architecture for Rails Teams

Stable Systems • Scalable Infrastructure • Measurable Results

I’m Lee Whittaker, a systems-focused engineer and Fractional CTO specializing in Rails architecture, DevOps reliability, and performance optimization.

I help product teams and growing companies stabilize fragile systems, eliminate scaling bottlenecks, and ship with confidence—without needing a full-time CTO on staff.

Work with me →

How I Help

Rails Architecture & Technical Leadership

  • Fractional CTO support for teams without senior technical direction
  • Architecture assessments using 4+1 and system-level mapping
  • Refactoring plans that reduce risk instead of spreading it around
  • Guidance on roadmap, trade-offs, and long-term maintainability

System Rescue, Performance & Reliability

  • Debugging brittle asynchronous pipelines and background jobs
  • Eliminating race conditions and data integrity issues
  • Performance tuning (throughput, latency, memory, N+1, indexing, etc.)
  • Infrastructure modernization with Docker, CI/CD, and observability

Modernization & Migration

  • Upgrading legacy Rails apps to supported, secure versions
  • Resolving UTF-8 / internationalization issues blocking global users
  • Stabilizing deploy pipelines and integrating with third-party APIs
  • Designing safer paths away from “big bang” rewrites

See how I work →

Recent Impact

  • 1,361 images processed in 2 minutes after redesigning an async image-processing pipeline
  • 60% memory reduction by migrating from Heroku buildpacks to a modern Docker-based deployment strategy
  • 118 failing tests resolved while upgrading a legacy choir-management system to current Ruby and Rails
  • High-risk concurrency bugs eliminated in a legal hearing scheduling platform where tests were passing but data was failing
  • Global UTF-8 encoding failures corrected, restoring international customer onboarding and search

These aren’t theoretical exercises—they’re real systems, in production, under real constraints.

What Clients Say

"Lee's contributions have significantly improved the efficiency and effectiveness of the Enterprise Program Management Office (EPMO), Benefits and Memorial (BAM) Services Portfolio, enabling the delivery of critical technology solutions to support the Veterans Benefits Administration (VBA) and National Cemetery Administration (NCA)."

Clayton Coleman
COO & Director of Engineering, J-Mack Technologies

"Lee absolutely raised the bar for our entire product line in that regard. He presented all of his findings and desired path forward to our internal Architectural Review Board, and his presentation received glowing reviews."

Matthew Thornton
Technical Lead, Booz Allen Hamilton

See all testimonials →

Recent Writing

I document real-world case studies from my work—what broke, why it mattered, how we fixed it, and the outcomes.

From Solo Practitioner to Team Multiplier: How Nine Years of Full-Stack Mastery Became a Four-Day Sprint That Changed How I Think About Technical Leadership

November 26, 2025 — Ruby on Rails, Software Development, Technical Leadership

How 9 years of solo full-stack experience translated into 2.5x team velocity through systemic architectural prep. First sprint planning delivered p…


Processing 1,361 Images in 2 Minutes: The Architectural Shift That Turned a Slow Rails Pipeline into a High-Throughput, Asynchronous System

November 25, 2025 — Ruby on Rails, Performance Engineering, Async Architecture

How we rebuilt a legacy synchronous Paperclip + S3 image pipeline into a fully asynchronous architecture—cutting processing time from 11 hours to 2…


The Complete Rails Docker Reference: Every Configuration File, Command, and Troubleshooting Guide You Need for Production-Ready Container Deployment

July 04, 2025 — Ruby on Rails, DevOps, Reference

Complete Rails Docker configuration reference with all Dockerfiles, GitHub Actions, Makefiles, and troubleshooting guides. Ready-to-use templates f…


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Who I Work With

  • SaaS and product companies whose Rails apps are critical to revenue
  • Growing teams that need senior architecture guidance without a full-time CTO
  • Founders and engineering leaders facing scaling, reliability, or modernization challenges
  • Organizations preparing for audits, investor scrutiny, or major growth

If your system feels fragile, slow, or risky, you don’t just need “more code.”
You need clear architecture, calm leadership, and a plan.

Let’s Work Together

Whether you’re fighting production fires, planning a major upgrade, or preparing your platform for the next stage of growth, I can help you stabilize your foundation and move forward with confidence.

Ready to talk?
Get in touch →

Clear architecture. Stable systems. Confident delivery.