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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

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