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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

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