About the role
We are looking for a Member of Technical Staff with 1+ years of experience to join a tiny, high-ownership team building the next interface for AI — a personal AI assistant that lives in iMessage. You'll be a product-minded full-stack engineer who has shipped something real to users and thrives in ambiguity. Caddy is backed by Y Combinator and Matrix Partners, has hundreds of monthly active users after launching just a month ago, and is scaling fast. This is a true founding engineer opportunity where you'll set the tone for both the product and the engineering culture.
What will you be doing?
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Building out Caddy's memory system — taking cutting-edge research on agent memory and retrieval and productizing it into something accessible for non-technical users
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Owning large, ambiguous problems end-to-end: choosing the approach, building the system, shipping to users, and iterating based on feedback
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Building integrations across consumer and work tools (email, Stripe, Oura Ring, Slack, Notion) to make Caddy truly proactive
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Working on frontier AI problems including agent reliability, context retrieval, and personalization
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Shipping fast in a 4-person team where everyone is a former founder and the pace is intense
