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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

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