Travel is a $4 trillion industry running on software from the last century. We are fixing that. is the leading marketplace for exceptional vacation homes with best-in-category guest satisfaction. OS takes that same battle-tested engine and puts it in the hands of every property manager on Earth: conversion-optimized direct booking websites, automated guest marketing, and AI-powered distribution to millions of travelers. Operators own their brand, their bookings, and their guests. No middlemen.

is led by a second-time founder and an all-star team from companies like Shopify. We are a Series B company gearing up for Series C, and product velocity has gone vertical: AI agents, payments, new distribution channels, and performance products, all shipping on a cadence most companies would call impossible. We call it Tuesday.

Our mission is to help people find their happy place. Our vision is to build the infrastructure for people to experience the world. If you want to make a dent in one of the largest industries on the planet, this is the place.

is building the future of hospitality, helping travelers find exceptional vacation homes. We're looking for a Senior Product Designer with outstanding visual craft to help make feel as remarkable as the homes and technology behind it.

You'll split your time roughly evenly between brand and product, working alongside our brand designer and partnering closely with Product and Engineering. This is a hands-on individual contributor role: most of your week is spent making things and shipping them.

• Help establish a distinctive visual language for through motion, illustration, and iconography.
• Design beautiful, intuitive, customer-facing experiences across web and mobile.
• Create brand moments for travelers and operators: campaigns, ads, launch assets, events, and presentations.

• Exceptional visual craft. You have a strong eye for typography, composition, color, and interaction design. Your work is thoughtful, polished, and unmistakably well designed.
• Motion, illustration, and icons. You have real depth in motion or illustration, strength in the other, and the ability to draw a clean, consistent icon set. You use them to bring personality and delight to our brand and product.
• Strong product thinking. You've shipped consumer products on web and mobile, and you can turn complex problems into simple, intuitive experiences.
• A builder's mindset. You love prototyping, exploring ideas in Figma, experimenting with AI, and bringing concepts to life with tools like Vercel. Even better if you build your own tools.
• An obsession with the details. You care deeply about design, from the overall experience down to the precise shade of gray. Sometimes a little too deeply. We get it.

We're a small, ambitious team that values experimentation, creativity, and strong opinions loosely held. We're looking for someone who can bring fresh ideas, elevate our visual identity, and make every experience feel more considered.

To apply, include a portfolio with shipped product work, plus motion, illustration, and icon samples.

• Exceptional visual and interaction craft, especially typography, composition, and polish.
• Demonstrated excellence in motion or illustration, strength in the other, and solid icon design. Not just a passing interest.
• Helps define a distinctive, elevated visual language across product and brand.
• Ships polished, customer-facing UI for wander and the app.
• Strong collaborator and hands-on builder.