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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

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