Benefits Manager

With millions of diners, 60,000+ restaurant partners and 25+ years of experience, Open Table, part of Booking Holdings, Inc. (NASDAQ: BKNG), is an industry leader with a passion for helping restaurants thrive. Our world‑class technology empowers restaurants to focus on what matters most – their team, their guests, and their bottom line – while enabling diners to discover and book the perfect restaurant for every occasion.

Every employee at Open Table has a tangible impact on what we do and how we do it. You’ll also be part of a global team and its portfolio of metasearch brands. Hospitality is all about taking care of others, and it defines our culture.

The Benefits Manager turns 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.

• 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 benefit 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.

• 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.

• 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.

• Work from (almost) anywhere for up to 20 days per year
• Focus on mental health and well‑being:
  Paid parental leave
• Generous paid vacation + time off for your birthday
• Paid volunteer time
• Focus on your career growth:
  Travel Discounts
• Employee Resource Groups
• Plenty of complimentary covered garage and outdoor parking spaces
• Complimentary membership to the Office Gym Facility
• Complimentary Uber Service to Darien and/or South Norwalk Metro North Station for sustainable commuting
• Free lunch 2 days per week
• Beautiful office in the suburb of Norwalk, Connecticut and easy…