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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

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