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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

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