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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

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