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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

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