Second Engineer
The voice interface that works proactively for you You’ll be our second engineer, working directly with Caddy’s founders on core architecture, product direction, and execution. If you’re excited about real-time systems, agentic workflows, and building a product you’ll use every day, you’ll have outsized impact here. You will own large, ambiguous problems end-to-end: from choosing the approach to shipping new features, operating them in production, and iterating based on user feedback. We work in person out of our SoHo office. Our tech stack is pragmatic and evolving. We care more about strong fundamentals than specific tools. Caddy is the operating system that works proactively for you. It learns how you work and acts on your behalf, keeping work moving while your context and voice stay intact. Instead of producing generic AI output, Caddy creates real work artifacts that sound like you and fit how you actually work. Today, it operates across the tools you use every day, including emai