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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

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