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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

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