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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

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