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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

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