Enrollment Specialist

Hilb Group

Enrollment Specialist managing Open Enrollment and New Hire processes for Hilb Group. Responsibilities include communication with benefit counselors, case management, and compliance support.

Posted 7/18/2026full-timeRemote • 🇺🇸 United StatesMid-LevelSeniorWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in managing enrollment operations, including building and configuring cases, coordinating licensed professionals, and ensuring compliance with regulatory requirements. Proficient in utilizing Microsoft Teams, Outlook, and other enrollment platforms to facilitate effective communication and operational efficiency.

Highest-signal resume keywords

Enrollment Operations ManagementMicrosoft Teams ProficiencyEmployee Benefits ExperienceOrganizational SkillsAttention to Detail

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Case ConfigurationEnrollment Platform KnowledgeStaffing CoordinationPerformance Metrics TrackingRegulatory Compliance

Soft Skills

Clear CommunicationMultitasking AbilityStakeholder Management

Tools & Technologies

Microsoft OutlookMicrosoft BookingsMicrosoft TeamsDynamics

Certifications & Qualifications

Licensing RequirementsLTC Certification

Industry Keywords

Employee BenefitsEnrollment ProcessesCall Center Workflows

About the role

Key responsibilities & impact

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, and 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

Requirements

What you’ll need

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

Comp & perks

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!