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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

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