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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

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