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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

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