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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

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