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