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