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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

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