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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

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