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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

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