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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

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