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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

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