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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

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