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