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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

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