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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

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