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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

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