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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

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