Benefits Specialist

  • San Francisco, CA
  • Full-time

Company Description

We believe the economy is better when everyone has access. When everyone has room to grow. No one should be left out because the cost is too great or the technology too complex. We started with a little white credit card reader but haven’t stopped there. We’re empowering the independent electrician to send invoices, setting up the favorite food truck with a delivery option, helping the ice cream shop pay its employees, and giving the burgeoning coffee chain capital for a second, third, and fourth location. We’re here to help sellers of all sizes start, run, and grow their business—and helping them grow their business is good business for everyone.

Job Description

Square is looking for talented and organized Benefits Specialist with experience in 401(k) administration, wellness, and perks program management to join the People- Total Rewards Team. The Total Rewards Team is responsible for driving people initiatives across our organization. Were a team of Specialists in Benefits, HR Operations, and Compensation. This is a full time role based in our San Francisco office reporting to the US Benefits Manager.

This is a great opportunity for someone who thrives in an all hands on deck environment, can wear multiple hats, and enjoys interacting with people. You are organized, detail-oriented, likes to move fast and knows when to be flexible.

You will:

  • Manage 401(k) retirement plan including but not limited to 5500 filing, NDT, audits, employee inquiries, and projects

  • Manage day-to-day administration and vendor management of Squares wellness programs and perks

  • Track and reconcile all benefit invoices to ensure timely payment and accurate accounting internally

  • Manage internal communication tools (wiki, emails, and slack)

  • Oversee benefits processing for new hires, terminations, and qualified life events by working closely with Squares insurance carriers and our HRIS tool, Workday

  • Work with the Business Systems team to resolve benefits-related system issues and propose process improvements for benefits administration

  • Manage our third party benefits call center and assist with weekly Benefits office hours

  • Assist with all aspects of Open Enrollment including coordinating and managing our company wide onsite benefit fairs

  • Communicate with employees regarding company benefit policies which include but are not limited to wellness initiatives, 401(k), and perks programs

  • Manage COBRA process

  • Contribute to other special benefits projects, both domestic and international, as required

  • Ensure company compliance with federal, state, and local laws, including required notice distribution, responding to government notices, and ensure reporting requirements are met in a timely manner

  • Assist our LOA Benefits Analyst on leave of absence and accommodations claims as needed



You have:

  • 3-5 years of previous Benefits experience

  • Experience using HCM (Workday a plus)

  • Basic knowledge of federal, state, and local laws

  • Ability to handle sensitive and confidential data

Additional Information

At Square, our purpose is to empower – within and outside of our walls. In order to build the best tools for the businesses and customers we support all over the world, we have to start at home with a workforce as diverse and empowered as our sellers. To this end, we take great care to evaluate all employees and job applicants equally, based on merit, competence, and qualifications. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability status, or any other characteristic protected by law. We encourage candidates from all backgrounds to apply and always consider qualified applicants with arrest and conviction records, in accordance with the San Francisco Fair Chance Ordinance. Applicants in need of special assistance or accommodation during the interview process or in accessing our website may contact us by sending an email to assistance(at) We will treat your request as confidentially as possible. In your email, please include your name and preferred method of contact, and we will respond as soon as possible.