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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

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