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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

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