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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

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