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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

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