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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

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