Benefits Lead

Whatnot is the largest livestream shopping platform in North America and Europe to buy, sell, and discover the things you love. We’re re-defining e-commerce by blending community, shopping, and entertainment into a community just for you. As a remote co-located team, we’re inspired by innovation and anchored in our values. With hubs in the US, UK, Ireland, Poland, and Germany, we’re building the future of online marketplaces—together.

From fashion, beauty, and electronics to rare collectibles like trading cards, comic books, and even live plants, our live auctions have something for everyone.

And we’re just getting started! As one of the fastest growing marketplaces, we’re looking for bold, forward-thinking problem solvers across all functional areas. 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.

We are looking for a strategic, experienced Benefits Lead to shape and scale our global benefits programs. You’ll partner closely with our Total Rewards team and executive leadership to design, implement, and optimize benefit offerings that reflect our values, support employee well-being, and drive engagement across our global team. This is a high-impact role focused on strategy, innovation, and execution.

• Own the end-to-end strategy, design, and execution of Whatnot’s global benefits programs, including Health, Retirement, Wellness, Time Off, and Voluntary offerings.

• Develop and lead our multi-year benefits roadmap, ensuring alignment with company values, evolving employee needs, and competitive benchmarks.

• Partner with cross-functional teams (People, Finance, Legal, and Ops) to launch new benefits initiatives, enhancements, and pilots that improve employee experience and retention.

• Serve as the primary contact for brokers and external partners, ensuring accountability, service quality, and cost-effectiveness.

• Own the annual renewal and open enrollment process, including vendor negotiations, employee communications, system updates, and compliance.

• Use data and employee feedback to analyze plan performance, monitor utilization, and make recommendations to enhance offerings or reduce waste.

• Lead global expansion efforts to localize benefits in new countries, partnering with international leaders to address market needs and ensure compliance.

• Drive strategic communications and education, ensuring employees understand and value their benefits package through thoughtful and accessible messaging.

• Stay ahead of benefits trends and regulatory changes to keep our programs competitive and compliant.

• Be a thought partner to leadership, helping shape how benefits reflect our company values and support the holistic well-being of a high-performance, distributed workforce

Team members in this role are required to be within commuting distance of our San Francisco, LA, or NYC hubs.

Curious about who thrives at Whatnot? We’ve found that embodying a low ego, growth mindset, and high-impact drive goes a long way here.

You're someone who thrives in fast-paced, high-ownership environments and wants to have a meaningful impact on the employee experience. You’re equal parts strategic thinker, operational doer, and empathetic partner. We’re excited for you to bring:

• 7+ years of experience in global Benefits roles, including 3+ years owning strategy, design, and implementation at a fast-paced tech or high-growth company.

• Strong benefits design acumen and the ability to craft programs that balance employee needs, cost sustainability, and compliance.

• Comfortable toggling between big-picture thinking and hands-on execution, especially in startup or scaling environments.

• Experience supporting international teams and building localized benefits programs across multiple countries.

• Strong project management skills and experience owning complex, multi-stakeholder rollouts.

• Excellent communication and stakeholder management skills – you make complex topics accessible and actionable.

• Experience with Workday

• Flexible Time off Policy and Company-wide Holidays (including a spring and winter break)

• 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.

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.