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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

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