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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

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