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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

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