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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

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