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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

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