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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

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