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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

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