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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

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