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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

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