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.
Yes. Cheeky-Fit Inc. lists open roles at cheeky-fit.com/careers for engineers, designers, and operators building an AI fashion network.
Yes. Cheeky is a remote-first startup. Roles are designed for distributed team members who move fast and think big about fashion technology.
Cheeky builds an AI fashion network: wardrobe digitization, AI styling, social discovery, and a global marketplace with 0% seller commission for brands.
Visit cheeky-fit.com/careers for current openings and application details. Email jpande-cfo@cheeky-fit.com if you do not see a matching role.
Cheeky-Fit Inc. is headquartered in Manassas, Virginia, United States, and operates as a remote-first company founded in 2024.
Cheeky hires engineers, designers, and operators. See the careers page for the latest job descriptions and team needs.
Cheeky-Fit Inc. is an early-stage fashion technology company founded in 2024 and accepted into Stripe's Accelerate program in June 2026.
Check cheeky-fit.com/careers for current opportunities or email jpande-cfo@cheeky-fit.com to inquire about internships and contract work.
Cheeky builds iPhone product experiences and web properties with modern engineering practices. Specific stack details are shared during the interview process.
Email jpande-cfo@cheeky-fit.com with recruiting questions or visit cheeky-fit.com/careers for open roles and application instructions.