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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

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