Helios Dev Shop Helios Dev Shop Log In
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

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