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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

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