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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

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