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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

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