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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

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