Enrollment Specialist

Hilb Group

8d • Remote

About The Position

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.

Requirements

• 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

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

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!

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: High school or GED