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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

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