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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

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