With millions of diners, 60,000+ restaurant partners and 25+ years of experience, OpenTable, 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 OpenTable 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.

About the job

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.

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.

Minimum 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 and Perks

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 commute off I-95 or Merritt Parkway with lots of building amenities, such as a gym, outdoor walking paths, close to shopping centers, multi-purpose rooms in-building cafe, and more.

The best connections happen face-to-face, whether you’re sitting down to dinner or having coffee with a coworker. That’s why OpenTable has adopted a hybrid workplace model. This role aligns with that approach, with an expectation of coming into the office two days a week—giving employees the best of both worlds: in-person collaboration and flexibility.

Note for MA applicants: It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

There are a variety of factors that go into determining a salary range, including but not limited to external market benchmark data, geographic location, and years of experience sought/required. 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.

Work Environment & Flexibility

At OpenTable, we pride ourselves on fostering a global and dynamic work environment. As a team member with us, you will benefit from a schedule tailored to accommodate a global workforce operating across multiple time zones. While the majority of your responsibilities may align with conventional business hours, there will be instances where you are expected to manage communications - via calls, Slack messages, or emails - outside of regular working hours to effectively collaborate with international colleagues, respond to restaurant partners, and/or address urgent matters. OpenTable will always abide by and consider local laws and regulations.

Inclusion

We’re committed to creating a workplace where everyone feels they belong and can thrive. We know the best ideas come when we bring different voices to the table, so we're building a team as dynamic as the diners and restaurants we serve—and fostering a culture where everyone feels welcome to be themselves.

If you need accommodations during the application or interview process, or on the job, we’re here to support you. Please reach out to your recruiter to request any accommodations.

#LI-Hybrid

Learn more about this Employer on their Career Site