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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

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