Cheeky is a remote-first team of engineers, designers, and operators building the AI fashion network that connects wardrobes, styling, social discovery, and commerce. We move fast, ship often, and care deeply about the product.
We want people who are energized by building something that doesn't exist yet.
Cheeky is not a place for people who want to be told what to do. It is a place for people who see what needs to happen and go make it real. We value energy, taste, ownership, and speed over credentials and process.
We are building at the intersection of AI, fashion, social, and commerce. The problems are real, the market is massive, and the team is small enough that every person shapes the product.
There are no layers between you and the product. Features you build today show up in the app tomorrow. At this stage, every engineer, designer, and operator has direct influence on what Cheeky becomes.
We are building on-device ML models for apparel detection, edge-to-cloud inference pipelines, and AI styling systems that understand real wardrobes. This is applied AI with a tangible product surface.
We are a remote-first team distributed across the US and internationally. We care about output, not hours. Build your schedule around when you do your best work.
We don't assign tickets. We share context, align on goals, and trust each other to figure out the best path forward. You'll own entire features from idea to production.
We bias toward action. Short cycles, fast feedback, real users. We would rather ship something imperfect and learn than spend months debating the ideal approach.
From API design to pixel spacing, we care about craft. Fashion is a taste-driven category, and the product needs to reflect that sensibility at every level.
Startups are hard. The people who thrive here are the ones who genuinely enjoy building, learning new things, and figuring out hard problems with a small group of people they respect.
Hire amazing people, give them real problems, and get out of the way.
We keep the team small on purpose. Fewer people means more ownership, faster decisions, and a product that reflects a coherent point of view instead of a committee's compromise.
We don't always have a specific role posted, but we are always open to meeting people who are exceptional at what they do. If Cheeky sounds like something you'd want to build, reach out.
jpande-cfo@cheeky-fit.comSend us a short note about what you do, what excites you, and a link to anything you've built. No formal resume required — show us your work.
Meet the founding team, explore the product, or download the app and start using it yourself.