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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

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