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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

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