Payroll & Benefits Specialist

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Department: Human Resources/Payroll

Office: Home Office

Location: West Springfield, MA

Job Description

About the Opportunity:

Aspen Square Management, one of the nation’s largest privately held real estate investment and property management firms, is seeking an ambitious Payroll & Benefits professional to join its growing HR team. The Payroll & Benefits Specialist position is an exciting opportunity to join a dynamic team providing a broad range of HR services in support of business objectives.  This role will work with the HR Operations team alongside the Payroll Administrator & HR Generalist. The ideal candidate has experience in payroll, benefits administration, a commitment to process and procedure and an ability to work within a dynamic, fast-moving, entrepreneurial organization.  The Payroll & Benefits Specialist reports to the HR Operations Manager.  This position offers a hybrid work schedule.

Role & Responsibilities:


  • Responsible for the day-to-day administration of the employee benefit programs including but not limited to; medical, dental, FSA, Disability, and 401k plans.
  • First point of contact for benefit related inquiries and responsible for ensuring legal compliance with Federal and State regulations & requirements including disability, FMLA, and 401k.
  • Manage employee benefit enrollment process, including running reports for payroll biweekly elections to ensure employees to input & audit employee elections
  • Communicate with benefit carriers and online benefits enrollment platform to resolve employee portal questions or enrollment issues.
  • Reconcile and approve monthly billing statements from carriers & vendors
  • Manage employee termination process for all employees- including process in HRIS, working with managers to ensure all necessary forms are completed timely, providing or coordinating benefit exit information including, unemployment and COBRA information.
  • Responsible for leave of absence administration, reporting and tracking, manage all LOA and related functions including FMLA/PFMLA, Disability, ADA, Worker’s Comp, & internal Company personal leave policies; coordinate with employees, supervisors, and carriers to ensure timely communication; manage process for benefit premium payments for employees are on leave.
  • Work with vendors & carriers to assure compliance including, COBRA, ERISA, 5500 reports, and ACA compliance.
  • Maintain summary plan description records, documents, and communications; manage required filings, reports and audits relations to the administration of employee benefit programs.
  • Develop employee wellness initiatives including coordination of employee wellness events, vendor participation and communication.
  • Responsible for executing leave administration process including, FMLA, PFMLA, Disability, Worker’s Comp and internal company leave programs; coordination of benefits while employees are on leave, maintenance of timecards and communication with leave carriers.
  • Run ad hoc reports as requested by HR Operations Manager
  • Assist with various HR-related tasks, special projects and reporting.




  • Cross-train in bi-weekly processing of multi-state payroll- assist Payroll Administrator with payroll tasks and required post payroll reporting.
  • Ensure compliance in multi-state/multi jurisdiction tax withholding, special payroll deductions.
  • Participate in payroll audits, workers compensation & 401k
  • Assist Payroll Administrator with timely processing of new hires and employee terminations
  • Maintain detailed records and documentation of all functions for audit purposes in accordance with statutory requirements
  • Identify needs and make recommendations to software systems and procedures as needed.

Qualifications & Requirements

  • Bachelor’s Degree in business administration, Human Resources or another associated discipline.
  • 3-5 years’ experience working in a payroll & benefits position.
  • Experience benefit laws, regulations including Section 125, ERISA, FMLA, COBRA, ACA
  • Strong knowledge of federal and state benefit and tax legislation required.
  • Experienced in HRIS systems and associated federal & state laws
  • Advanced proficiency with MS office software, Excel required.
  • Strong analytical skills and proficiency
  • Attention to detail, excellent verbal and written communication skills
  • Must be able to main handle sensitive and confidential information

About the Company:

Aspen was founded sixty years ago by local entrepreneur and philanthropist Harold Grinspoon when he purchased his first duplex. Mr. Grinspoon’s incredible business and financial success growing Aspen Square Management allowed him to start his own Foundation and become one of 136 pledgers nationwide who joined the Giving Pledge established by Warren Buffet and Bill and Melinda Gates. That same entrepreneurial spirt that drove the launch of the company is still very present today.

Based in West Springfield, MA, Aspen Square Management owns and manages approximately 14,000 apartment units in fifteen states. Known for its fast-paced, people-centric culture, Aspen invests heavily in value-add repositioning and has acquired, renovated and managed over 50,000 apartments in our history (check out our 1 minute “Our Story” video at to see an Aspen transformation!) All apartment community operations are supported from our Home Office which employs about 100 of our 600 employees, while the majority of our employees work from our seventy plus apartment communities located throughout the country. Financially sound, positioned for continued growth, and known for excellence in management within the multi-family housing industry, Aspen is an incredible place to grow your career and truly make a positive impact on people.


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