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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

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