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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

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