Benefits Specialist

  • St. Louis, MO
  • Full-time

Company Description

Square builds common business tools in unconventional ways so more people can start, run, and grow their businesses. When Square started, it was difficult and expensive (or just plain impossible) for some businesses to take credit cards. Square made credit card payments possible for all by turning a mobile phone into a credit card reader. Since then Square has been building an entire business toolkit of both hardware and software products including Square Capital, Square Terminal, Square Payroll, and more. 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 to assist with the daily 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 with our LOA Program Manager, both based in San Francisco. This is a great opportunity for someone who excels in an “all hands-on deck” environment, and enjoys working with people.

You will:

  • Manage the daily outsourced leave of absence administration acting as liaison between the vendor, employees, managers, and HR while ensuring compliance with laws and regulations. 
  • Be the leave of absence 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 by email, virtual meetings, and in person.
  • Troubleshoot and help resolve issues related to leave of absence file feed into Workday and leave of absence payroll calculations
  • Monitor the status of all leaves of absences; take measures to ensure all necessary updates and communications are provided to employees and leave process is efficient
  • Provide customer service
  • Complete applicable state disability and paid family leave claims received
  • Other benefits-related projects and responsibilities


You Have:

  • Previous Leave of Absence administration experience 
  • Experience handling accommodation cases
  • Adept ability to communicate both verbally and written with employees at all levels
  • Expert level organizational skills
  • Well versed in both state and federal employment laws
  • Excellent interpersonal skills
  • Easily adjust to varying work environments
  • Effective time management

Additional Information

At Square, we value diversity and always treat all employees and job applicants based on merit, qualifications, competence, and talent. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We will consider for employment qualified applicants with criminal histories in a manner consistent with the requirements of 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.


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