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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

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