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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

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