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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

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