Lead, Benefits

About the Company Gemini is a global crypto and Web3 platform founded by Cameron and Tyler Winklevoss in 2014, offering a wide range of simple, reliable, and secure crypto products and services to individuals and institutions in over 70 countries. Our mission is to unlock the next era of financial, creative, and personal freedom by providing trusted access to the decentralized future. We envision a world where crypto reshapes the global financial system, internet, and money to create greater choice, independence, and opportunity for all — bridging traditional finance with the emerging cryptoeconomy in a way that is more open, fair, and secure. As a publicly traded company, Gemini is poised to accelerate this vision with greater scale, reach, and impact. The Department: People The Role: Lead, Benefits Reporting to the Associate Director, Total Rewards & Payroll, the Lead, Employee Benefits will own Gemini’s employee benefits and leave administration functions across the United States and Singapore. This role is responsible for the strategy, administration, compliance, vendor management, communication, and continuous improvement of Gemini’s employee benefits and leave programs while delivering a high-quality employee experience. As the subject matter expert for Benefits and Leave Administration, you will have end-to-end accountability for health and welfare programs, employee leaves, vendor partnerships, compliance, reporting, and employee education. You will partner closely with Payroll, Finance, Legal, People Business Partners, Talent Acquisition, managers, and external vendors to ensure our programs remain competitive, compliant, and operationally effective. This role requires exceptional judgment, discretion, analytical thinking, and the ability to independently drive strategic initiatives while maintaining strong day-to-day execution in a fast-paced environment. Responsibilities: Own Gemini’s employee benefits and leave administration functions across the United States and Singapore. Lead the strategy, administration, communication, and continuous improvement of all employee benefits and leave programs. Evaluate market trends, employee feedback, utilization data, and business needs to recommend competitive and innovative benefits offerings. Lead benefits renewals in the United States and Singapore, including vendor evaluations, negotiations, plan design recommendations, implementation, and ongoing program management. Own the annual U.S. Open Enrollment process, including planning, system configuration, testing, employee communications, enrollment support, and post-enrollment reconciliation. Manage employee leave programs in partnership with third-party vendors, including FMLA, disability, parental leave, statutory leaves, company-sponsored leaves, and other applicable leave programs. Serve as the primary point of contact for leave administration vendors, ensuring timely case management, accurate employee communications, regulatory compliance, and a consistent employee experience throughout the leave lifecycle. Partner with People Business Partners, Payroll, Legal, managers, and external vendors to coordinate complex leave and accommodation cases. Maintain appropriate confidentiality while ensuring stakeholders receive the information necessary to effectively support employees and manage business operations. Serve as the primary relationship manager for benefits brokers, carriers, leave administrators, consultants, and other external vendors, holding partners accountable to service levels, contractual commitments, and compliance requirements. Partner with Payroll, Finance, Legal, and People Operations to ensure accurate benefits administration, payroll deductions, funding, reporting, and regulatory compliance. Develop and execute employee communications and education initiatives that improve awareness, understanding, and utilization of Gemini’s benefits and leave programs. Partner with Talent Acquisition to ensure employee benefits are accurately and effectively represented throughout the candidate experience. Build and maintain benefits and leave reporting, dashboards, and analytics to measure utilization, cost, vendor performance, employee engagement, and program effectiveness. Monitor leave trends, case management outcomes, vendor performance, and employee feedback, and recommend improvements to strengthen the employee experience and operational efficiency. Standardize, document, and continuously improve benefits and leave processes, controls, policies, and procedures across supported jurisdictions. Ensure compliance with all applicable federal, state, and local requirements within the United States, as well as applicable benefits and leave requirements in Singapore. Act as the escalation point for complex and sensitive employee benefits and leave questions. Support internal and external audits, regulatory reporting, testing, and compliance activities related to benefits and employee leaves. Identify opportunities to automate processes, strengthen controls, reduce administrative burden, and improve service delivery. Partner with the broader Total Rewards team on strategic initiatives where benefits or leave expertise is required. Minimum Qualifications: Bachelor’s degree in Human Resources, Business Administration, or a related field, or an equivalent combination of relevant education, training, and experience. 8+ years of progressive experience administering and managing employee benefits programs. Demonstrated experience owning a corporate benefits function with end-to-end accountability. Experience supporting benefits programs in the United States and international markets; experience supporting Singapore is strongly preferred. Demonstrated experience leading U.S. benefits renewals and annual Open Enrollment. Experience administering employee leave programs in partnership with third-party vendors, including FMLA, disability, parental leave, and other statutory or company-sponsored leave programs. Working knowledge of U.S. employee benefits and leave requirements, including FMLA, ADA, and applicable state and local leave laws. Experience managing benefits brokers, carriers, leave administrators, consultants, and third-party vendors. Strong analytical, problem-solving, and critical-thinking skills, with the ability to make data-informed recommendations. Excellent project management and organizational skills, with the ability to independently manage multiple priorities and deadlines. Strong client-service orientation and the ability to manage complex or sensitive employee matters with discretion and empathy. Excellent written and verbal communication skills, including the ability to explain complex benefits and leave information clearly. Demonstrated judgment and ability to manage highly confidential and sensitive information. Strong attention to detail and commitment to operational accuracy. Ability to thrive in a fast-paced and evolving environment while balancing strategic initiatives with day-to-day execution. Preferred Qualifications: Experience administering benefits through Dayforce and/or Workday, including benefits configuration and Open Enrollment. Experience supporting a transition from Workday to Dayforce or another HRIS or payroll platform. Experience administering employee benefits and leave programs in Singapore. Experience managing third-party leave administration vendors and supporting complex leave and accommodation cases. Experience supporting benefits implementations, HRIS migrations, or system optimization initiatives. Experience developing benefits and leave communications, employee education programs, and manager resources. Demonstrated ability to use analytics to evaluate and improve benefits and leave program effectiveness. Proven ability to identify opportunities for automation, process improvement, stronger controls, and improved employee service. Demonstrated abi…