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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

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