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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

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