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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

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