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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

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