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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

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