Benefits 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 Benefits 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:

• Onboard and manage client cases on our proprietary platform by configuring the system based on their benefit plans (e.g., core, voluntary and spending plans), ensuring alignment with summary plan descriptions, eligibility rules, and termination guidelines.

• Handle customer inquiries with clear, accurate solutions; manage escalated issues, troubleshoot discrepancies, and maintain regular communication to update clients on resolutions and progress.

• Build strong client relationships through proactive needs anticipation, one-on-one interactions, and advocacy for their feedback within the organization.

• Act as a liaison between clients and internal teams, facilitating training, renewals, and community participation to maximize value and retention.

• Troubleshoot platform behavior, including coverage calculations, data exchange issues, and unexpected behaviors such as calculation errors.

• Create test scenarios and validate platform functionality through quality assurance, defect tracking, and peer reviews to perfect the user experience.

• Set up and manage EDI and API integrations using industry formats like ANSI 834; handle secure file transfers, configurations, and detailed documentation.

• Collaborate with end users, carriers, and internal teams as a benefits administration subject matter expert, communicating with carriers to clarify rules and gather data for enhancements.

• Create and maintain user documentation, training materials, job aids, knowledge checks, support documentation for user processes, and a technical knowledge base to support clients and internal teams.

• Reconcile large volumes of platform data with carrier invoices using advanced Excel skills to ensure accuracy, validate findings, and resolve inaccuracies through analysis and adjustments.

• Analyze data patterns, trends, and customer pain points to uncover issues, report discrepancies between systems, and drive strategic decisions.

Qualifications:

• Bachelor's degree in a related field or equivalent professional experience; minimum 5 years in a client-facing benefits administration role at an insurance agency, with strong knowledge of group benefits, medical plans, self-insured plans, ancillary lines, and fringe benefits.

• Exceptional customer service and communication skills; ability to break down complex problems and explain them clearly.

• Advanced technical proficiency in benefits platforms, Excel (including pivot tables and VLOOKUPs) for data reconciliation, and tools like Microsoft Office, Jira and Confluence.

• Understanding of carrier integrations, proprietary and EDI 834 file formats; experience with benefits administration, renewals, billing audits, and eligibility management.

• Strong problem-solving skills to independently identify and resolve issues; ability to handle multiple assignments, large data sets, and context-shift in a startup-like environment.

• 1-2 years of customer service or account management experience; demonstrated passion for client satisfaction, attention to detail, and initiative in a fast-paced, metric-oriented setting.

• Strong technical aptitude, preferably in SaaS environments;

• Reliable remote work setup with a dedicated workspace and high-speed internet.

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.