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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

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