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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

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