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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

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