Benefits Manager - Hybrid

Position Description

Title: Benefits Manager
Department: Human Resources
Location: Sarasota, FL
Immediate Supervisor: VP, Total Rewards and HR Systems
Status: Salaried Exempt

Position Purpose

The Benefits Manager is responsible for overseeing the daily administration of all benefit programs across the United States, Union environments, and Canada.

Principle Accountabilities

• Team Leadership & Daily Operations
  Manage the work of the benefits team, ensuring timely and accurate completion of tasks.
  Provide training and coaching on problem-solving, customer service, and procedural questions.
  Support and oversee the execution of benefit communications and engagement activities, including employee messaging, enrollment materials, and educational resources.

• Partner with leadership and vendors to ensure communications are accurate, timely, and aligned with program goals to promote employee awareness and participation.

• Benefits Administration (US, Union, and Canada)
  Oversee daily operations of all benefit programs, including health, dental, vision, disability, life, retirement, and ancillary plans.
  Ensure benefit eligibility, enrollment, qualifying life events, and payroll deductions are processed accurately.
  Review and resolve escalated issues related to union benefit administration, ensuring alignment with CBA requirements.
  Support Canadian benefits operations by monitoring accuracy, troubleshooting discrepancies, and partnering with the Canadian HR team.
  Lead the annual 401(k) match calculation for the US.

• Vendor & Carrier Coordination
  Oversee day-to-day interactions with carriers, brokers, and third-party administrators.
  Monitor vendor service delivery and escalate performance concerns as needed.
  Support annual renewal processes by making recommendations, gathering data, validating documentation, and coordinating vendor tasks.
  Participate in vendor meetings; provide operational insights and issue tracking.

• Dayforce (Benefits)
  Review and validate Dayforce configuration and testing completed by the benefits team and HRIS/Payroll.
  Ensure accuracy of benefit enrollment rules, eligibility groups, and deduction logic.
  Oversee resolution of Dayforce data discrepancies and partner with HRIS/Payroll on corrections.
  Maintain a working knowledge of system functionality and partner with the VP Total Rewards on developing the benefits roadmap.

• Compliance & Documentation
  Ensure benefits are administered in compliance with plan documents, CBAs, and regulatory requirements (ACA, ERISA, HIPAA, provincial laws).

• Support internal and external audits by providing data, documentation, and explanations.
  Create and/or maintain up-to-date standard operating procedures for all benefit processes.
  Monitor routine legislative updates and escalate required plan changes to VP Total Rewards.

• Billing, Funding & Financial Accuracy
  Oversee team completion of billing reconciliation for all benefit plans.
  Review funding files for accuracy and ensure timely submission.
  Escalate complex financial issues, overpayments, or discrepancies to leadership.

• Open Enrollment & Ongoing Communication
  Coordinate and lead operational tasks for annual enrollment, including timelines, testing support, vendor materials review, and employee communications.
  Ensure the team executes enrollment changes and resolves employee questions promptly.

• Projects & Process Improvements
  Support benefit-related projects, such as vendor transitions, system updates, and M&A integration tasks.
  Recommend improvements to increase consistency, accuracy, and efficiency of benefits operations.
  Ensures processes are documented and team adopts any new procedures.

Essential Skills And Experience

• Bachelor’s degree or equivalent experience preferred.
• 5–7+ years of experience in benefits administration (US or Canada; union experience a plus).
• Strong attention to detail and ability to manage multiple priorities.
• Solid working knowledge of benefits regulations and plan administration processes.
• Proficiency in HRIS systems; Dayforce experience preferred but not required to be deep/technical.
• Strong communication and customer service skills.
• Ability to troubleshoot issues and escalate appropriately.
• Comfortable working with vendors and cross-functional partners.