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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

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