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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

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