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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

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