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Provided by the employer
Verified Pay check_circle $75,000 per year
Hours Full-time, Part-time
Location 165 FLANDERS ROAD
WESTBOROUGH, Massachusetts open_in_new

About this job

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, communications and annual renewals.
  • Support in preparation of cost analyses of employee health and welfare benefits including calculating annual benefit premiums, employee contributions, and benefit budget by plan and location.
  • Participate in various employee benefit surveys, summarize the results and develop recommendations to maintain competitive, cost-effective benefits.
  • Identify, suggest and implement ongoing process improvements.  Review, interpret, and apply benefit plan documents, leave laws and regulatory requirements to ensure consistent and compliant administration
  • Ad hoc report generation for HRIS/HWSE as needed.
  • Maintain Leave of Absence policy ensuring regulatory compliance with local, state and federal laws.  Comprehensive knowledge of benefit plan design, adeptness at interpreting relevant laws, and proven skill in addressing issues within benefits framework, regulatory standards, policies, and procedures.

 

Peripheral Duties:

  • Reconciles, prepares, and processes all benefit invoices - using processes outlined by carriers and ensures company is paying invoices on time and within terms.
  • Comprehensive knowledge of benefit plan design, adeptness at interpreting relevant laws, and proven skill in addressing issues within benefits framework, regulatory standards, policies, and procedures
  • Covers all eligible associates and dependents elected.
  • Updates payroll and/or vendor systems as needed for benefits enrollments and terminations.
  • Removes all associates and dependents that are no longer eligible such as terminations, age limitations, etc. 
  • Compliance with COBRA regulations.
  • Remains current on all vendor billings.
  • In synch with carrier and Accounts Payable on billing.
  • Miscellaneous related duties or projects assigned.

Working Relationships:      HRIS team, Finance, Payroll, IT, Senior Leadership

Requirements

Education and Experience: 

  • Graduation from an accredited four-year college or university.
  • Five - Seven years of experience as a Benefits Analyst. 
  • Any equivalent combination of education and experience.

Necessary Knowledge, Skills, and Abilities:

  • Considerable knowledge of modern policies and practices of personnel administration; considerable knowledge of employee benefit programs, including medical and dental, retirement, disability, and unemployment;
  • Strong HRIS experience: navigation, data entry, reporting, trouble-shooting;
  • High proficiency in Microsoft Office tools (Word, Excel, Outlook, Teams), SharePoint, UKG, and practical experience using Ben-Admin enrollment and leave management systems
  • Skill in preparing and administering surveys; skill in analyzing benefit programs, costs, and alternatives; skill in operating the listed tools and equipment;
  • Ability to analyze and interpret comprehensive benefit information; ability to carry out assigned projects to their completion. Ability to communicate effectively verbally and in writing; ability to establish and maintain effective working relationships with applicants, employees, company officials; ability to understand and follow instructions.
  • Excellent communication skills, strong teamwork and collaboration with internal and external stakeholders, the ability to handle sensitive information with discretion while providing exemplary customer service
  • Resilience; ability to handle our internal customers with grace, delivering excellent customer service.

 

Driving/Travel Requirements:

  • There are no current driving requirements for this position. This is subject to change.
  • This job requires 0% domestic travel. 
  • This position is based in Westborough Massachusetts and requires the employee to be Onsite 4 days a week

Special Requirements:

  • Must have the ability to research individual states and the governing laws regarding benefits and leaves of absence.

Tools and Equipment Used:

  • Work computer, including word-processing, database, and spreadsheet programs.
  • Smartphone required.

Physical Demands:

  • The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions. 
  • While performing the duties of this job, the employee is frequently required to sit and talk or hear. The employee is occasionally required to walk; use hands to finger, handle, or feel objects, tools, or controls; and reach with hands and arms. 
  • The employee must occasionally lift and/or move up to 25 pounds. Specific vision abilities required by this job include close vision and the ability to adjust focus. 
  • This job requires 100% working in front of a computer.

Work Environment:

  • The work environment characteristics described here are representative of those an employee encounters while performing the essential functions of this job. Reasonable accommodation may be made to enable individuals with disabilities to perform the essential functions.      
$75000

Job Benefits

At Cumberland Farms, it’s important that our employees reflect the world we live in and the communities we serve. We celebrate our differences, so your unique background and skillset could bring a wonderful new perspective to our team. If you have a passion for delivering exceptional results, thrive in a fast-paced corporate environment, and bring experience in business management or related areas, we'd love to meet you - even if you don't meet every single requirement.

Consistent with Massachusetts Pay Transparency Law, we’re sharing the base salary range for this position. Final pay within this range will be based on your skills, experience, and qualifications. Base pay represents just one part of our total rewards approach. We’re proud to offer a variety of financial and non-financial benefits that invest in your overall growth, well-being, and career journey.


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Posting ID: 1271678473 Posted: 2026-08-12 Job Title: Benefit Analyst