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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

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