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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

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