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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

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