Who we are

We are a product-obsessed team on a mission to give people back their time. We believe the calendar is one of the most powerful tools in the world, and we're building it the way it should have been built from the start.

We've raised $7M from investors like Altos Ventures, Y Combinator (S18), Joe Gebbia (Airbnb Co-founder), Steve Chen (YouTube Founder/CTO), and Dick Costolo (former Twitter CEO). Our users range from fast-moving startups to Fortune 500 companies, and they trust us with the most valuable real estate in their day.

We don't care where you got your degree or if you even have one. Here's what we look for in everyone we hire:

Warmth
Clear thinking
Bias towards over-communication
Excessive attention to detail

Technologies we work with:

Ruby on Rails
React
Typescript
Claude

The role

AI is changing what a calendar can be and we're moving fast to explore what that means for our users. We're looking for a senior AI Product Engineer who can work across the full stack to bring intelligent, delightful features to life.

This isn't a pure ML or research role. You'll be building product: integrating LLMs and AI APIs into a real application, designing the UX around AI-powered interactions, and owning features end-to-end.

Some of the features you'll build include agentic scheduling experiences, such as finding times that work across multiple attendees with packed calendars, identifying conflicts before the user sees them, and surfacing smart suggestions without the back-and-forth. The calendar is a harder technical problem than it looks. Behind a simple grid of meetings lies high webhook traffic, continuous calendar syncing, complex time-zone logic, recurring event handling, and multiple third-party API integrations. The work spans frontend (React), backend (Ruby on Rails), and AI/LLM integration.

What you'll do

Design, build, and ship AI-powered features from scratch: scheduling assistants, smart suggestions, natural language interfaces, and more
Build beautiful, high-quality frontend experiences in React and TypeScript
Work across the stack, from ideation in Claude Design to shipping new APIs and UI to prod
Maintain high reliability in a system people depend on 30-40 times a day
Deliver new features to users on a regular cadence, keeping momentum high and making sure progress is always visible

You might be a great fit if you

Have 3+ years of software engineering experience, including hands-on experience building and shipping LLM or AI-powered features in production
Have worked with React and TypeScript (bonus: Ruby on Rails or another dynamic backend language)
Have strong product instincts and care deeply about user experience
Are genuinely excited about AI, not just as a tool but as a design surface
Thrive with full ownership and a fast shipping cadence
Know how to build reliably with AI: designing for model limitations, handling failures gracefully, and making smart tradeoffs between what's possible and what's production-ready
Love to code, regardless of how you got here — our team includes people from economics, law, and bootcamp backgrounds

Nice to have

Experience with agentic AI patterns, RAG, function calling, or multi-step LLM workflows
Contributions to open source or experience teaching programming
Interest in self-improvement and productivity tools
Experience working on small, highly productive engineering teams