Benefits Specialist

Job Locations US-IL-Chicago
Job ID
People Team

About The Opportunity

We’re all about connecting hungry diners with our network of over 300,000 restaurants nationwide. Innovative technology, user-friendly platforms and streamlined delivery capabilities set us apart and make us an industry leader in the world of online food ordering. When you join our team, you become part of a community that works together to innovate, solve problems, grow, work hard and have a ton of fun in the process!


Why Work For Us

Grubhub is a place where authentically fun culture meets innovation and teamwork. We believe in empowering people and opening doors for new opportunities. If you’re looking for a place that values strong relationships, embraces diverse ideas–all while having fun together–Grubhub is the place for you!


The Impact You Will Make

The Benefits Specialist is responsible for the day-to-day management of Grubhub’s health and welfare and retirement savings plan benefits. This role will also be the primary administrator for Grubhub’s leave and disability programs. 



  • Administer various benefits programs including medical, dental, vision, disability, life insurance, fsa, commuter benefits and 401(k) plans.
  • Serve as primary liaison for employee questions.
  • Work with benefit vendors to quickly resolve issues.
  • Manage all aspects of leave of absence and disability programs including providing policy information to employees, working closely with our third-party administrator, collaborating with HR Business Partners, providing timely pay updates to our Payroll team, creating benefit premium invoices and monitoring cases.
  • Assure accuracy/reconciliation of premium invoices and coordinating payments through Accounting.
  • Monitor online benefit enrollments and changes, auditing as necessary.
  • Participate in the annual renewal process and strategy. 
  • Assist with the Open Enrollment process including development of materials, communications, system testing and auditing.
  • Assist with ensuring all benefit plan compliance requirements are met including testing, auditing, Form 5500 filings, required notices and 1095-C reporting/filing.
  • Partner with our internal Culture and Community team on wellness initiatives and other benefits-related events.
  • Develop and oversee communication of benefits and educational opportunities throughout the year including quarterly 401(k) sessions.
  • Manage all Workers Compensation claims and oversee OSHA filings.


What You Bring to the Table

  • Bachelor’s degree in human resources, business or related field
  • 3+ years direct benefit administration experience
  • Proficient in Excel
  • Experience in UltiPro/UKG preferred
  • Strong working knowledge of FMLA, ADA, Workers’ Compensation, Affordable Health Care Act and federal and state laws regarding benefits (e.g. ERISA, Sec. 125, COBRA etc.)
  • Ability to manage multiple critical, time-sensitive projects simultaneously in a fast-paced environment
  • Strong communication and organizational skills

And Of Course, Perks!

  • PTO. Grubhub employees are provided a generous amount of time to recharge their batteries. 
  • Health and Wellness. We provide programs that support your overall well-being such as generous medical benefits, employee network groups, company-wide fitness challenges, and a comfortable and casual workplace! We also support our parents by offering 8 weeks of paid parent bonding time, a 4-week returnship program, and 6-8 weeks paid medical leave.
  • Learning and Career Growth. Your personal and professional development is a priority at Grubhub. From day one, we empower you to lead and be an active participant in your career growth.  We provide continuous learning opportunities, training, and coaching and mentorship programs.  
  • MealPerks. Who’s ready for some lunch? We provide our employees with a weekly Grubhub credit  to enjoy and support local restaurants. We also offer company-wide meals several times a year to bring our Grubhub family together.
  • Fun. Every Grubhub office has an employee-led Culture Crew that connects people through fun, meaningful events and initiatives. Some of our popular past events include: Wing-eating contests, Grubtoberfest, 5k Runs, Bring Your Child to Work Day, regular happy hours, and more!
  • Social Impact. We believe in the importance of serving the communities that support our business. In addition, employees are given paid time off each year to support the causes that are important to them. 

Grubhub is an equal opportunity employer. We evaluate qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status, and other legally protected characteristics. The EEO is the Law poster is available here: DOL Poster. If you are applying for a job in the U.S. and need a reasonable accommodation for any part of the employment process, please send an e-mail to and let us know the nature of your request and contact information. Please note that only those inquiries concerning a request for reasonable accommodation will be responded to from this email address.  


CA Privacy Notice: If you are a resident of the State of California and would like a copy of our CA privacy notice, please email 


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