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

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