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 email, calendar, Slack, Linear, and Notion.

Caddy is built by the team behind Loom’s AI and core product. We believe the next era of computing is software that understands intent, handles ambiguous work, and quietly gets work done in the background.

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.

What we’re looking for

• Obsessed with building a product that not only our users love, but that you love and want to use every day
• Can make and defend thoughtful product and technical tradeoffs
• Thrive in ambiguity and default to ownership
• Care about correctness, performance, and user experience
• Move fast and with intention
• Strong opinions, loosely held

What you’ll do

• Own core systems for real-time voice → intent → action workflows
• Design APIs/services for long-running, stateful agent tasks
• Ship user-facing features with strong quality and polish
• Improve reliability, observability, and performance as we scale
• Help set product direction and company culture as the team grows

Our tech stack

Our tech stack is pragmatic and evolving. We care more about strong fundamentals than specific tools.

• TypeScript (required)
• Swift, Objective-C (bonus)