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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

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