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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

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