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Benefits Analyst

Job in Westborough, Worcester County, Massachusetts, 01581, USA
Listing for: Cumberland Farms, Inc.
Full Time position
Listed on 2026-08-14
Job specializations:
  • HR/Recruitment
    Regulatory Compliance Specialist
Salary/Wage Range or Industry Benchmark: 70000 - 96000 USD Yearly USD 70000.00 96000.00 YEAR
Job Description & How to Apply Below

Are you curious about solving complex business challenges for a leading convenience retailer? Do you have a passion for cross functional collaboration? Then you may be the perfect addition to our team!

Cumberland Farms is one of the fastest-growing convenience retailers in the United States, committed to becoming America’s #1 ‘one-stop’ destination. The business has an established pedigree of delivering excellent fuel, grocery and merchandise, and food service. Headquartered in Westborough, Massachusetts, our Company has grown to over 1,500+ locations across the United States employing over 18,000 team members. You can find us operating under the following store banners:
Certified Oil, Cumberland Farms, Fastrac, Kwik Shop, Loaf N Jug, Minit Mart, Sprint Food Stores, Tom Thumb, Turkey Hill, and Quik Stop. Our US headquarters in Westborough, MA is home to our Store Support Center, Company Warehouse, and Culinary Center.

What We Offer:
  • Competitive Wages
  • Work today, get paid tomorrow through our earned wage access program*
  • Paid Time Off
  • Medical/Health/Dental Coverage
  • 401K with Company Match
  • Team Member Discounts
  • Tuition Reimbursement
  • Employee Assistance Program
  • Health Savings Account
  • Company Spirit Days
  • Employee recognition and awards
  • And much more!
Position Summary:

The Senior Benefits Analyst supports the company’s benefits plan directives in determining plan design, implementation, compliance, and administration of the company’s U.S. Health & Welfare and retirement benefits. This candidate oversees compliance with all federal, state, and local regulations and company policies and procedures regarding medical (FMLA, STD, LTD) and military leaves, workers’ compensation, and Americans with Disability Act requirements.

Essential Duties and Responsibilities:
  • Benefits Administration:
    Manage employee benefits change requests; communicate weekly payroll changes to the payroll department and carriers; employee benefits communication; new hire orientation; employee education. Assist in yearly and strategic benefit planning;
    Open Enrollment meetings, communication and education.
  • Health & Welfare HRIS
    - Monitor for any potential issues, resolving as appropriate with UKG, ensure benefits data integrity between the HRIS and carriers and payroll system, trouble-shoot employee technical issues.
  • Leave of Absence administration:
    Point of contact for managing employee leaves of absence; work with plan vendor on administration; maintain close communication with management, payroll team and employee; manage employee benefit invoicing.
  • 401(k):
    Responsible for enrollment process, employee questions, loans/withdrawals, vendor liaison and bi-weekly deferral transmittal; work with vendors in annual plan audit and discrimination testing; assist in the Form 5500 submission; employee communication and education. Reconcile 401(k) and deferred compensation funding, and update all 401(k) weekly election changes.
  • Remain abreast of local, state and federal requirements, rules, regulations and mandates regarding employee benefits; advise company officials on benefit regulations and options.
  • Agent of the Company:
    Serve as a filter for information, able to support the Company goals and protect its interests.
  • Create a unique value-added place on the HR team:
    Act as a regular contributor to team discussions; develop/maintain open communication and strong relationships with all other team members.
  • Conduct accurate and timely monthly carrier billing reconciliation; address any corrective action and educate other team members.
  • Engage in analysis, evaluation, design, development and implementation of plan modifications and enhancements, including participation in obtaining senior leadership approval.
  • Utilize strong working knowledge of employee benefits to assist in the design, planning and administration of corporate employee benefit programs.
  • Facilitate the annual benefits Open Enrollment process including plan and employee communication. Coordinate tasks internally and externally and ensure that HRIS and vendors are updated with employee enrollments and costs.
  • Work with outside vendors, insurance providers and legal counsel on plan modifications,…
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