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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

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