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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

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