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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

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