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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

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