Head of Global Leaves and Benefits

Asana•San Francisco, CA

5d•$207,000 - $243,000•Hybrid

About The Position

The People Team at Asana works to enable all Asanas to achieve our goals as a company in a way that is consistent with our values. We focus on recruiting, developing, and retaining exceptional talent from diverse backgrounds, ensuring that everyone can thrive, grow, and make a meaningful impact. Our work The People Team at Asana works to enable all Asanas to achieve our goals as a company in a way that is consistent with our values. We focus on recruiting, developing, and retaining exceptional talent from diverse backgrounds, ensuring that everyone can thrive, grow, and make a meaningful impact. Our work supports Asana’s broader mission: to help humanity thrive by enabling all teams to collaborate seamlessly and effectively. As the Head of Global Benefits & Leaves, you will lead the strategy, design, and operations of our global benefits and leave of absence programs. This is a critical leadership role overseeing a team of three and reporting directly to the VP of Total Rewards & People Operations. You’ll own the full portfolio—health and welfare, retirement, wellness, perks, and leave programs across all regions—ensuring our offerings are competitive, cost-effective, and deeply aligned with Asana’s culture. A key near-term priority for you will be driving the strategic migration of our leave administration platform from Matrix to Larkin. This role is based in our San Francisco office with an office-centric hybrid schedule. The standard in-office days are Monday, Tuesday, and Thursday. Most Asanas have the option to work from home on Wednesdays. Working from home on Fridays depends on the type of work you do and the teams with which you partner. If you're interviewing for this role, your recruiter will share more about the in-office requirements.

Requirements

10+ years of progressive experience in benefits and/or leave administration, with at least 3 years of people management.
Deep expertise in U.S. benefits and leave programs, complemented by meaningful experience managing international benefits.
Proven track record of not just administering programs, but designing and executing strategy from the ground up.
Experience leading technology migrations (e.g., leave platforms, BenAdmin systems, or HRIS integrations).
Strong analytical skills for cost modeling and the ability to translate complex benefits topics into clear narratives for senior leadership.
Proven ability to drive accountability and value from brokers, carriers, and TPAs.
Genuine passion for employee experience and a belief that benefits are a meaningful expression of company culture.
Demonstrates curiosity about AI tools and emerging technologies, with a willingness to learn and leverage them to enhance productivity, collaboration, or decision-making.

Responsibilities

Set the global benefits roadmap across health, retirement, wellness, and perks, ensuring alignment with Asana’s total rewards philosophy.
Own the annual benefits renewal cycle, including plan design evaluation, carrier negotiations, and cost modeling for leadership recommendations.
Drive global benefits harmonization efforts, balancing a consistent employee experience with local market competitiveness and compliance.
Lead the global leave of absence program strategy, including parental, medical, and statutory leaves, ensuring they are competitive and clearly communicated.
Mentor, coach, and develop a team of three: US Benefits Manager, International Benefits Manager, and Leave of Absence Program Lead.
Partner with Legal and Finance to ensure compliance with global regulations (ERISA, ACA, HIPAA, FMLA, etc.) and support new-market entries or M&A activity.
Drive process improvements and systems optimization to improve data integrity and reduce manual work across the benefits ecosystem.