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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

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