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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

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