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