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