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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

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