Benefits Lead

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.

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