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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

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