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Benefits Analyst

Job in Westborough, Worcester County, Massachusetts, 01581, USA
Listing for: Cumberland Farms
Full Time position
Listed on 2026-07-13
Job specializations:
  • Business
    Regulatory Compliance Specialist
Salary/Wage Range or Industry Benchmark: 75000 - 105000 USD Yearly USD 75000.00 105000.00 YEAR
Job Description & How to Apply Below

Description

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

This is a critical member of the benefits team responsible for overall administration and communication of all Health & Welfare benefit plans and programs. Position ensures compliance with all regulatory requirements as well as internal policies and practices. Responsible for the development and maintenance of all communication materials to support benefit Plans and Programs as well as compliance documentation. Manages the Well Being program, including assisting in the development and communication of program guidelines, and execution of all related activities.

Responsibilities
  • Administers health and welfare benefits, including enrollment data, reconciliation of billing, and audits/controls to gain efficiencies while ensuring accuracy and timeliness.
  • Ensures documentation of all regulatory requirements and policies, including but not limited to ERISA documents, HIPAA compliance and training, and required disclosures for benefits. Ensures integrity of data to support reporting and documentation requirements. Maintains all related documents in soft and hard copy and ensures the distribution of all necessary compliance related notices to participants.
  • Develops and maintains relationships with external partners/vendors, ensuring effective management of outsourcing and collaboration.
  • Analyzes current and future enrollment in all benefits plans to identify trends to refine benefits budget.
  • Develops and executes targeted communications to enhance employee understanding of the benefits plans, policies, and events, including all communication related to Wellbeing Program.
  • Provides insight and tools to the benefits function in order to automate and develop efficiencies in all benefits processes.
  • Maintains reporting of benefits metrics, capturing, enrollment, cost and trend. Works with external Benefits Consultant (Marsh & McLennan) for support on industry data and trends.
  • In collaboration with Benefits Specialist, plans and executes annual Open Enrollment, including Benefit Fairs held at SSC, as well as development of the Benefits Guide distributed to all eligible team members.
  • Works with internal partners to assist with the planning, execution and support of the annual Year End Meeting. Works with Benefits Team to strategize theme, materials and execution of Benefits booth at this Meeting.
  • Administers Retiree Program, including retiree letters, gold cards and coordination of invitations to Year End meeting.
  • Serves as back-up for administration of Retirement Plans.
  • Coordination of the annual Boston Globe Top Workplaces program, when deemed appropriate to participate.
  • Serves as a resource to all team members on all matters relating to Benefits, ensuring compliance with all service level commitments.
  • Provides support and expertise to benefits team with respect to special projects and daily tasks as needed.
Working Relationships

HRIS team, Finance, Payroll, IT,…

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