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Benefits Specialist

Boston, MA, USA Req #3765
Wednesday, April 24, 2019
WinnCompanies Benefits team is currently revamping, developing, and implementing a new robust multiyear benefit strategy and looking for an experienced Benefits Specialist to join us. You will be part of a lean team creating and implementing new benefits that will be regionalized across 22 states and D.C. You will also be an integral part in the implementation and rollout of a new employee benefit and enrollment platform, providing the opportunity to showcase your unique project management  skills. If you have new ideas, like to voice your opinions, and want to be part of an exciting organizational change, this is the opportunity for you!

Essential Functions
  • Administer health and welfare benefit plans including, but not limited to: medical, dental, life, disability, and supplemental programs.
  • Ensure compliance with state and federal laws affecting group benefit management administration, including but not limited to: ACA, HIPAA, COBRA, ERISA, FMLA, Section 125, Qualified Medical Child support Orders, Form 5500, USERRA and state regulations.
  • Participate in annual benefits renewal.
  • Audit health and welfare benefit plan enrollment data to ensure accuracy.  
  • Reconcile and process monthly carrier premium invoices and ensures timely payment.
  • Process monthly funding of HSA accounts.
  • Administer all aspects of the leave of absence program; develop strong working relationships with vendors and third-party administrator (TPA) to ensure accurate, efficient, and timely claims administration and excellent customer service.
  • Partner with third-party administrator (TPA) to oversee eligibility, tracking and reporting, ensuring compliance with FMLA and ADA and reasonable accommodation oversight.
  • Maintain a Leave Log to support the tracking of all leaves of absences.
  • Collaborate on appropriate handling of benefits impacted by leaves of absence, return-to-work, and end-of-employment such as; medical, dental, life, and disability.
  • Advise and counsel employees and their dependents on existing benefits.  
  • Maintain contact with insurance carriers, third-party administrators, employees and beneficiaries to facilitate proper and complete utilization of benefits for all employees.
Job Requirements
  • Bachelor's degree 
  • 3 - 5 years of benefits experience
  • Proficient in Microsoft office, and very comfortable using Excel 
  • Excellent written and verbal communication skills

WinnCompanies Corporate Culture & Benefits

WinnCompanies is a fast-growing, award-winning national housing development and property management company with 3,000 team members working in 22 states and the District of Columbia. We offer opportunities for growth across the country. One-third of our team members were promoted to the positions they hold today. 


We are always looking for outstanding team members who work with a passion for excellence, a “can do” results-oriented attitude and a dedication to quality. Our most successful team members are hardworking, responsible, customer-oriented individuals who are committed to improving the communities where they work.


Founded in 1971, WinnCompanies is a Drug Free Workplace and an Equal Opportunity Employer that values and encourages diversity within the workplace. Nearly half of our workforce is comprised of women or minorities. In addition to training and recognition programs to help you succeed, we offer competitive Health, Dental, Life and Disability Insurance benefits, and a generous 401(k) plan.

Other details

  • Pay Type Salary
  • Required Education Bachelor’s Degree
  • Job Start Date Wednesday, April 24, 2019
  • Boston, MA, USA