Global Benefits Manager

Sierra • San Francisco, CA

9d • Onsite

About The Position

At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New York, London, France, Singapore, and Japan.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.

Requirements

• 7+ years of experience in global benefits, total rewards, or related People functions, ideally in high-growth tech environments.
• Deep knowledge of U.S. and international benefits, including health and welfare plans, pension/retirement schemes, statutory programs, and leave regulations across multiple regions.
• Strong experience managing benefits vendors, brokers, and renewals, with an ability to negotiate, benchmark, and maintain cost-effective programs.
• Excellent communication skills with the ability to explain complex benefits clearly, partner across executive and functional teams, and deliver an exceptional employee experience.
• A systems thinker with strong project management skills, capable of balancing strategic planning with hands-on execution.

Nice To Haves

• Experience supporting global expansion and entity setup in new countries.
• Familiarity with HRIS, ben-admin platforms, and payroll integrations.
• CEBS, GBA, PHR, or similar benefits-related certification.

Responsibilities

• Design, implement, and manage Sierra’s global benefits programs including health plans, retirement, wellness, leave programs, and local statutory benefits ensuring they are competitive and compliant across all regions.
• Partner cross-functionally with People, Finance, Legal, and global leaders to support benefits strategy, budget planning, M&A/due diligence needs, and new-country expansions.
• Manage vendor relationships and brokers across the U.S., EMEA, and APAC to drive service excellence, cost efficiency, renewal strategy, and regulatory compliance.
• Serve as a trusted advisor to employees, providing clear guidance on benefits, leaves, eligibility, and policy interpretation while ensuring a smooth, high-touch experience.
• Build scalable systems, reporting, and documentation, using data and market insights to evaluate program effectiveness, anticipate global needs, and evolve offerings as Sierra grows.

Benefits

• Flexible (Unlimited) Paid Time Off
• Medical, Dental, and Vision benefits for you and your family
• Life Insurance and Disability Benefits
• Retirement Plan (e.g. 401K, pension) with Sierra match
• Parental Leave
• Fertility and family building benefits through Carrot
• Lunch, as well as delicious snacks and coffee to keep you energized
• Discretionary Benefit Stipend giving people the ability to spend where it matters most
• Free alphorn lessons

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 251-500 employees