Enrollment Specialist

Grow With Us! At Hilb Group, we recognize that our associates are our greatest asset. We promote a service-driven culture of high performance that encourages career and professional development. The Hilb Group is currently seeking a motivated and ambitious Enrollment Specialist to join our team. The ideal candidate will be motivated to succeed, is well organized, able to prioritize, and able to work well with a team. This is a remote position.
Responsibilities:

• Build and configure Open Enrollment and New Hire cases across systems

• Review case details (dates, carriers, products, platforms, licensing)

• Manage Microsoft Bookings, Teams chats, and Outlook calendar entries

• Maintain booking links, case communications, and platform access

• Partner with Account Managers, Implementation Managers, and internal teams

• Gather and validate requirements, timelines, and special considerations

• Communicate enrollment details to Benefit Counselors, including: Schedules Platforms and carriers Licensing/certification requirements Compensation structure

• Determine staffing needs based on enrollment scope and requirements

• Assign counselors based on availability, experience, and utilization

• Maintain staffing trackers, backup plans, and availability schedules

• Finalize enrollment calendars

• Maintain case build checklists to ensure accuracy

• Confirm platform builds and counselor access

• Manage licensing and certification requirements (including LTC)

• Conduct final readiness checks prior to launch

• Monitor Teams chats and call center inboxes during enrollment

• Resolve access issues and missed appointments

• Track daily activity, premiums, and performance metrics

• Provide operational insights to leadership

• Generate reports on enrollment, staffing, and utilization

• Identify trends, risks, and opportunities for improvement

• Support compliance with regulatory requirements

• Transition Open Enrollment cases to New Hire status

• Update systems, calendars, and communications

• Ensure accurate case closeout and cleanup

• Support enrollment operations as directed by the Director of Enrollment Services

Qualifications:

• Minimum High School degree

• Strong organizational and multitasking skills

• Ability to manage multiple timelines and stakeholders

• High attention to detail and accuracy

• Clear written and verbal communication

• Employee benefits or enrollment experience

• Familiarity with Microsoft Teams, Outlook, Bookings, and Dynamics

• Experience coordinating licensed professionals

• Knowledge of enrollment platforms and call center workflows

• Experience working across multiple systems and tools

Benefits: 

• Company Paid Life Insurance, Long-Term and Short-Term Disability.

• Medical, Dental, Vision and FSA/HSA plans.

• 401(k) with company match.

• Additional voluntary benefits including Critical Illness, Accident Insurance, Hospital Indemnity and Supplemental Life Insurance, Legal and Identity Protection, and Pet benefits.

• Generous PTO.

• An awesome team of professionals!

The Hilb Group is an equal opportunity employer, and we actively support and comply with all applicable federal, state, and local laws prohibiting all forms of discrimination in employment. Additionally, we have a zero-tolerance policy for all forms of harassment in violation of federal, state, and local laws.