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