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Jason Fleetwood-Boldt

About Jason Fleetwood-Boldt

I've spent 20+ years building large applications: high-quality, tested codebases. I did TDD in Rails from the start, and I've always advocated for pair programming: two developers, one task. Now that coding isn't the bottleneck anymore, and judgment is the name of the game, pair programming feels more relevant than ever.

I'm also a lifelong learner and teacher at heart. I write about the craft (see my "Automated Testing from 10,000 Feet" crash course on testing and TDD) and built Hot Glue, an open-source Rails Turbo toolkit with 100k+ downloads. Mentoring junior engineers through a hard refactor is one of my favorite parts of the job.

On the business side: I've been an IC, a lead engineer, and a VP at Mack Weldon, where the platform my team built scaled the company to $30M. I've also worked as a lead architect bridging strategy and execution at places ranging from early-stage startups to Charles Schwab. These days I'm deep in agentic engineering and LLM orchestration: RAG, vector similarity search, and building AI systems with turn-based state management and autonomous workflows.

Past Clients & Technologies

Bootstrap SimpleCov Webhooks SendGrid Perplexity OAuth WebMock OpenAI GitHub Actions Sass Cypress SQL Distributed Systems Plaid PostCSS Webpacker CI/CD FactoryBot Pundit CSS Docker Ruby on Rails CircleCI Hotwire Resque Elasticsearch React DeepSeek Datadog VCR Mailgun Prompt Engineering Redis RDS RAG AI Agents ActiveStorage Devise Turbo Swift MongoDB Meta Graph API S3 JavaScript WebSockets Google APIs Stripe Node.js Stimulus Python RSpec Capybara CloudWatch HAML EC2 jQuery Git iOS pgvector Terraform ActionCable Vector Search Google Analytics GraphQL Vite HTML Sidekiq MySQL Mux Nginx NextJS New Relic Heroku NestJS AWS Jest TypeScript PostHog PostgreSQL LLM Systems