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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

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