Senior Benefits Administrator

Senior Benefits Administrator

Posted Wednesday, August 19, 2026 at 4:00 AM

Stew Leonard's, a family-owned and operated fresh food store founded in 1969, has locations in Connecticut, New York, and New Jersey. Stew's earned its nickname, the  Disneyland of Dairy Stores  because of its country-fair atmosphere, with costumed characters and animated entertainment throughout the store that keep children entertained while parents shop.

Stew Leonard's seeks a skilled and motivated Senior Benefits Administrator to join our team! The Senior Benefits Administrator serves as a strategic and operational partner in planning, administration and continuous improvement of the organization's team member benefit offerings. Working closely with the Benefits Manager, this role helps drive the benefits program strategy by managing complex benefits programs, leading open enrollment, supporting vendor relationships and ensuring regulatory compliance across all offerings.

The Senior Benefits Administrator is responsible for the day-to-day operations of health and welfare plans and retirement programs. This is a professional role requiring independent judgement and the ability to perform complex work with minimal supervision. The ideal candidate brings deep expertise in benefits support, strategy and operations, excellent analytical skills and a passion for delivering a best-in-class team member experience.

This role offers a strong platform for professional development. As our company continues to expand, we look for team members who want to grow their skills and take on new challenges. With a solid track record of internal promotion, we routinely partner high-potential team members with proven mentors. While future advancement depends on business needs and individual performance, we are deeply committed to promoting from within whenever possible.

This is an onsite role which is based at our Danbury, CT office.

• Acting as main contact for team member's benefit administration and support. Provides superb customer service, resolving benefit inquiries from team members and vendors in a timely manner.
• Monitors Dayforce File Transfers for completeness, addressing and resolving errors as needed or escalating and coordinating error resolution with Dayforce case management, as needed. Documenting details and providing case updates to team/vendors/manager.
• Gathers team member data, processes benefit invoices and performs monthly billing and enrollment audits.
• Helps to establish and deliver the annual benefits communication strategy, including maintaining and updating the Benefits Website, creating content for all locations and communications avenues in partnership with the Benefits Manager.
• Supports the annual open enrollment process including preparing the open enrollment module in Dayforce, updating Dayforce benefit rate tables, coordinating updates to the benefit brochure and open enrollment communication materials, coordinating and delivering open enrollment information sessions, tracking elections, implementing open enrollment changes, performing open enrollment audits and scrubbing data to prepare for the new plan year and partnering with benefits vendors as needed.
• Subject Matter Expert for Stew Leonard's benefits. Keeps abreast of federal, state and local laws affecting company benefit programs. Informs, updates and maintains programs for compliance.
• Provides input to and develops content for team member benefits communications, including, a regular cadence of promotion and education materials that support building understanding and reinforcing the value of our benefits programs.
• Collaborates with Benefits Manager on benefits related events including benefit fairs, financial and wellness solutions, and retirement education seminars.
• Peak support:
  Must work on the store floor during peak seasons.
• Other duties as assigned

• Responsible for yearly completion of Section 125 Non-Discrimination Testing.
• Responsible for maintaining, reviewing, correcting, submitting 1095/1094 – C/B forms as required by ACA rules.
• Delivery of all required materials such as SPD's, SBC's, COBRA, SAR notices, and other annual notices.
• Independently researches issues, gathers data and advises on findings in the general benefits area.
• Manages and maintains up to date procedural documentation for all benefits role job duties.
• Related work, as required.

• Bachelor's degree in HR, Business or related field from an accredited college, or equivalent experience/combined education.
• 7+years in HR/Payroll, with a minimum of 4 years in benefits experience required.
• Industry certifications such as CEBS, PHR/SPHR, SHRM-CP/SHRM-SCP or CBP/CCP coursework are a plus.
• Experience with Dayforce, including HRIS administration, reporting and open enrollment configuration.
• Exceptional attention to detail and superior organizational skills.
• Excellent interpersonal and communication skills, including the ability to explain complex problems and maintain…