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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

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