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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

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