Benefits Specialist

About Stripe

Stripe is a financial infrastructure platform for businesses. Millions of companies—from the world’s largest enterprises to the most ambitious startups—use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone’s reach while doing the most important work of your career.

The Benefits team is fundamental to the Stripe experience and enablement, directly supporting our global workforce. The Benefits team ensures our offerings are competitive, clearly understood, and fully compliant with local regulations across 27 countries, consistently evolving our benefits strategy to meet the diverse needs of our employees.

We are seeking a Benefits Specialist, experienced in benefits administration, to join our team in the U.S. This position requires a strong background in addressing benefits-related inquiries from employees in multinational technology organizations, significant experience with US benefits operations, leave administration, file integrations, and billing and reconciliation.

• Lead and execute compliance related projects such as ACA reporting, HCSO, and 5500 reporting.
• Respond to questions regarding benefit enrollment status, Workday assistance, general benefits coverage details, retirement or pension contributions, time off, leaves of absences, benefit new hire questions, and more.
• Administer benefit enrollments, approvals, and reports within Stripe’s vendor portals.
• Proactively review process and policy documentation to identify opportunities and streamline operations.
• Process Workday events such as qualified life events, time off corrections, event corrections, leave of absence requests, etc.
• Manage vendor eligibility files and error reporting / corrections to ensure timely and accurate eligibility data to all carriers.
• Manage benefits invoices by inputting data for invoice generation, reconcile and review invoices for accuracy, and work with finance ops to ensure timely payment and efficient processes are in place.
• Execute open enrollment operations including Workday testing, employee meetings, and file feed and integration updates and processing.

We’re looking for someone who meets the minimum requirements to be considered for the role. If you meet these requirements, you are encouraged to apply. The preferred qualifications are a bonus, not a requirement.

• 1-3 years of experience in an employee-facing benefits operations role with US-based insurance, Workday, and benefits experience required.
• A strong understanding of employee benefits programs and the ability to explain complex information in a clear, empathetic way to Stripes.
• Experience using Workday (specifically the Benefits and Time Off modules).
• Enjoy problem-solving and are comfortable working across teams to resolve issues and drive process improvements.
• Experienced in maintaining accuracy regarding benefits enrollments and invoicing to enable vendors to access accurate eligibility and payment data
• Strong english communication skills (written and verbal required).
• Detail-oriented, analytical, and adaptable, with a continuous improvement mindset.
• Strong operational execution and organizational skills.
• Discretion and judgment handling confidential and sensitive data.

• Experience in working on AMER benefit portals like - Forma, HMSA, Risco etc would be a plus.
• Experience working in a fast paced, growing environment, preferably in a technology company or large scale organization.
• Experience utilizing company policies and practices to determine appropriate recommendations.
• Experience with benefits operations and programs in EMEA and APAC are a plus.