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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

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