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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

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