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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

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