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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

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