Benefits Specialist

  • St. Louis, MO, USA
  • Full-time

Company Description

When we launched the little white reader, we invented mobile, ubiquitous payments and enabled anyone to start, run, and grow a business. Ten years and billions of transactions later we’re reimagining commerce for businesses of all types and sizes—we’re enabling the independent electrician to send invoices, helping the beauty salon pay its employees, and giving the burgeoning coffee chain capital for a second, third, and fourth location. We’re working to find new and better ways to help businesses succeed on their own terms—and we’re looking for people like you to help shape tomorrow at Square.

Job Description

Square is looking for a Benefits Specialist with great customer service and organizational skills to assist with the day-to-day outsourced leave of absence administration, accommodation process, and onsite benefits support.  This is a full time role based in our St. Louis office reporting to the US Benefits Manager but working very closely with our LOA Program Manager, both based out of San Francisco.

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. 

Essential Duties/Responsibilities

  • Manage the day-to-day outsourced leave of absence administration acting as liaison between the vendor, employees, managers, and HR while ensuring compliance with laws and regulations. 

  • Serve as leave of absence subject matter expert familiar with leave of absence and disability provisions

  • Administer accommodation requests including reviewing cases, documenting requests, consulting with employees, HRBPs, supervisors, and Legal team  

  • Respond to employee and HR inquiries related to leave of absence benefit programs primarily via email, virtual meetings, and in person as appropriate.

  • Troubleshoot and assist in resolution of issues related but not limited to leave of absence file feeds into Workday and leave of absence payroll calculations

  • Monitor the status of all leaves of absences; take proactive measures to ensure all necessary updates and communications are provided to employees and leave process is efficient

  • Deliver superior written and verbal customer service

  • Responsible for completing applicable state disability and/or paid family leave claims received

  • Other benefits-related projects and responsibilities


You Have:

  • Previous Leave of Absence administration experience 

  • Previous experience handling accommodation cases 

  • Proven critical thinking and problem-solving skills

Even Better:

  • Excellent verbal and written communication skills

  • Detail oriented and highly organized

  • Ability to communicate with employees at all levels of the organization

  • Strong knowledge and understanding of both state and federal employment laws

  • Excellent interpersonal skills

  • Ability to adapt to a fast paced continually changing business and work environment while managing multiple priorities

  • Effective time management skills

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. Perks At Square, we want you to be well and thrive. Our global benefits package includes: Healthcare coverage, Retirement Plans, Employee Stock Purchase Program, Meal reimbursements, Wellness perks, Paid parental leave, Flexible time off, Learning and Development resources