Benefits Manager

About the role

As the Benefits Manager, you turn our total rewards strategy into impactful, easy-to-use programs that support employees across their work and life journeys. In this role, you will own the day-to-day administration, continuous improvement, and compliance of our health, retirement, leave, and wellbeing offerings. By bridging strategic planning with hands-on operational excellence, you will ensure seamless plan delivery, accurate system configuration, and clear employee communications. You will also partner closely with cross-functional teams to provide empathetic support and drive innovative, data-backed program enhancements.

Responsibilities

• Lead end-to-end planning and execution for annual renewals, open enrollment, and plan design updates while managing relationships with brokers and insurance carriers to ensure service quality and cost-efficiency.
• Analyze benefit utilization, cost trends, and market benchmarking data to propose innovative program enhancements aligned with our global philosophy.
• Execute and maintain strict regulatory compliance and governance for all benefit plans, including funding compliance, non-discrimination testing, and required annual notices.
• Oversee policy definition, workflow enhancement, legal notices, and administration for leave of absence programs across North America.
• Partner with technology teams to build, test, and maintain Human Resources Information System benefits configurations, life event tracking, and vendor data integrations.
• Manage high-tier benefits inquiries via internal ticketing systems and educate cross-functional teams on ongoing plan administration, open enrollment changes, and policy updates.

Qualifications

• 5+ years of progressive benefits experience, with proven experience leading plan administration, annual renewals, and open enrollment end-to-end.
• Deep knowledge of United States benefits compliance, including federal and state leave laws, and governance protocols.
• Hands-on experience with Human Resources Information Systems, demonstrating proficiency in benefits configuration, open enrollment setups, and integration troubleshooting.
• Proven track record of setting and administering leave of absence policies and holding brokers, providers, and technology vendors accountable to service levels.
• Strong communication and analytical skills with the ability to translate complex benefit data into clear executive recommendations and employee-friendly guidance.
• Ability to work 2 days from the office.

Preferred Qualifications

• Experience supporting benefits in a fast-paced technology, marketplace, or matrixed global company.
• Knowledge of Canadian, Mexican, UK, and European based statutory and supplemental benefits.
• Experience maintaining ticketing systems and internal knowledge bases.
• Relevant industry credentials such as Certified Employee Benefit Specialist, Certified Benefits Professional, or equivalent human resources certifications.

Benefits

• Work from (almost) anywhere for up to 20 days per year.
• Focus on mental health and well-being:
  • Company-paid therapy sessions through SpringHealth.
  • Company-paid subscription to Headspace.
  • Annual company-wide week off a year - the whole team fully recharges.
• Paid parental leave.
• Generous paid vacation + time off for your birthday.
• Paid volunteer time.
• Focus on your career growth:
  • Development Dollars.
  • Leadership development.
  • Access to thousands of on-demand e-learnings.
• Travel discounts.
• Employee Resource Groups.
• Free lunch 5 days per week.
• Beautiful office in the Empire State Building with amenities such as a gym, multi-purpose room, in-building Starbucks, and more.

Pay

The range for this United States located role is $125,000-$140,000 USD. We offer a competitive base salary and benefits including: health benefits; flexible spending account; retirement benefits; life insurance; paid time off (including PTO, paid sick leave, medical leave, bereavement leave, floating holidays, and paid holidays); and parental leave benefits. This role is eligible to be considered for an annual bonus.

Schedule

OpenTable has adopted a hybrid workplace model. This role requires coming into the office two days a week, allowing for in-person collaboration and flexibility. While the majority of responsibilities align with conventional business hours, occasional communication outside regular working hours may be needed to collaborate with international colleagues, respond to restaurant partners, or address urgent matters.