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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

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