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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

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