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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

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