Senior Art Director, 2D Illustration

Join the Future of Commerce with Whatnot!

Whatnot is the largest live shopping platform in North America and Europe to buy, sell, and discover the things you love. Whether it's trading cards, fashion, electronics, or live plants, our sellers are building real businesses across hundreds of categories. We're building live commerce at a scale that's never been done in the West, and there's no playbook to copy. The people here are shaping how an entirely new industry develops.

As a remote co-located team, we're inspired by our values and anchored in hubs across the US, UK, Ireland, Poland, Germany, and Australia. We move fast, stay close to our users, and focus on the work that drives the most impact.

We're one of the fastest growing marketplaces and were recently named the #1 Best Startup Employer in America by Forbes. Check out the latest Whatnot updates on our news and engineering blogs and join us as we enable anyone to turn their passion into a business and bring people together through commerce.

Role

Whatnot is looking for a multidisciplinary Designer and Illustrator to join the Brand Experience team as an Art Director, 2D Illustration. We’re a small, collaborative team of 2D and 3D illustrators and designers that care deeply about our respective craft. The Brand Experience team works across a wide range of surfaces at Whatnot, including digital experiences, marketing campaigns, growth, events, and merchandise.

This is a hands-on generalist role for someone with a high level of taste, craft, and creative range. This person should show a strong ability to simplify complex concepts into unique, intuitive, and visually compelling metaphors. The role requires a strong point of view and an ability to communicate actionable feedback or guidance to the team, empowering them to do their best work. This role requires a self-starter who is driven, proactive, and truly loves the creative process and working with others in a collaborative setting. They are comfortable working in ambiguous, fast-paced environments while maintaining a high level of craft. The right person brings strong 2D design craft, a point of view on art direction, and the ability to make smart creative calls with minimal guidance or information. Someone who isn’t afraid to experiment or learn new skills and keeps a pulse on design trends, propelling Whatnot’s visual identity in the creative vanguard.

In this role, you will:

• Develop visual strategies, art direction, and creative to extend Whatnot’s brand into digital experiences, product launches, events, social, and other high-impact surfaces.

• Work collaboratively across business verticals with designers, engineers, copywriters, marketers, and creative leads from the initial brief to delivery.

• Move fast from the initial brief to execution, cutting scope when possible while maintaining a high bar for craft.

• Maintain and evolve visual strategies through moodboards and sketches to create bespoke, beautiful, production-ready assets.

• Bring a meticulous eye with an ability to communicate actionable feedback in a productive way.

• Maintaining a collaborative and positive environment that motivates the team to do their best work.

• An ability to see a project from start to finish, with an ability to verbalize the concepts in a convincing manner.

• Works with tools like Figma, Adobe Creative Suite, and AI workflows to communicate ideas, streamline processes, and make the work better, faster.

• Keep a pulse on current fashion and design trends, pop culture, commerce, creators, and the Whatnot community to create a genuine connection to a wide variety of demographics.

We offer flexibility to work from home or from one of our global office hubs, and we value in-person time for planning, problem-solving, and connection. Team members in this role must live within commuting distance of our San Francisco, New York, Seattle or Los Angeles hubs.

You

People who do well at Whatnot tend to be comfortable figuring things out as they go, biased toward action, and genuinely curious about what they're building. They care more about outcomes than credit and stay close to the product and the people using it.

As an Art Director, 2D Illustration, you should have 7+ years of experience across brand, campaign, or creative studio work, with a portfolio that shows strong visual thinking and hands-on execution. You know how to make work that looks great, moves quickly, and solves the actual problem.

Candidates should have:

• Experience — industry experience creating work for similar products or brands, in-product experiences, visual identities, large-scale campaigns, social media, and merchandise.

• Storytelling — showcases an exceptional ability to communicate ideas, stories, and narratives through static and animated creative assets.

• Taste — a portfolio or presentation showcasing a high level of taste, strong art direction, strategy, knowledge, and experience working within or developing visual systems, and highly polished illustration and graphic design solutions.

• Creative Tools — proficiency in Figma, Adobe Creative Suite, Figma Weave, ChatGPT, Claude, Gemini, and other creative tools.

• Driven — this role requires someone that is driven with a ‘figure it out’ mentality. They are proactive, curious, and passionate about making great creative.

• Meticulous — You know when to templatize, when to self-edit, and where to push in order to deliver the best possible outcome.

• Self-Belief — you have experience leading creative work from start to finish, while collaborating closely with brand, product, engineers, and other cross-functional partners.

• Self-awareness — we’re looking for someone with a low-ego, and a high sense of ownership. You’re able to identify new opportunities to push our work and the brand. You’re able to take and deliver hard feedback in a thoughtful way, catered to each person’s personality and preferences of work style. You’re also able to see when the team needs you to jump in and get your hands dirty.

• Creative Buffer — showcase a strong ability to refine ambiguous briefs, find the real problem, and create an actionable gameplan for themselves or teams they partner with.

• Move uncomfortably fast — you’re comfortable working in a fast-paced environment and making decisions with incomplete information.

• Experimental —This person is self-motivated, and loves learning new skills or tools. They’re not afraid to push their work, within reason, to evolve Whatnot’s brand into the creative vanguard.

• Respected — this person is well-respected in the design community, and maintains strong ties to industry peers.

Nice to have:

• Experience in a high-growth startup, marketplace, consumer app, creator platform, or fast-moving creative studio.

• Experience in art directing motion, illustration, design, or creating capsule collections in fashion.

• Passion for AI tools and experimentation with vibe coding.

• Experience building illustration systems for in-house creative teams.

• Building creative tools to help support a large-scale design organization.

Benefits

• Generous Holiday and Time off Policy

• Health Insurance options including Medical, Dental, Vision

• Work From Home Support

  • Home office setup allowance

  • Monthly allowance for cell phone and internet

• Care benefits

  • Monthly allowance for wellness

  • Annual allowance towards Childcare

  • Lifetime benefit for family planning, such as adoption or fertility expenses

• Retirement; 401k offering for Traditional and Roth accounts in the US (employer match up to 4% of base salary) and Pension plans internationally

• Monthly allowance to dogfood the app

  • All Whatnauts are expected to develop a deep understanding of our product. We're passionate about building the best user experience, and all employees are expected to use Whatnot as both a buyer and a seller as part of their job. Our dogfooding budget makes this fun and easy.

• Parental Leave

  • 16 weeks of paid parental leave + one month gradual return to work. Company leave allowances run concurrently with country leave requirements which take precedence.

Please note: Whatnot will only contact you through official @whatnot.com email addresses. If you see an email impersonating a Whatnot recruiter, please disregard and report it as spam.

EOE

Whatnot is proud to be an Equal Opportunity Employer. We value diversity, and we do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, parental status, disability status, or any other status protected by local law. We believe that our work is better and our company culture is improved when we encourage, support, and respect the different skills and experiences represented within our workforce.