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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

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