Seasonal Enrollment Specialist Lead

We’re Looking For

We are fanatical about serving our customers and contributing to their success. We are looking for someone with strong communication skills who can build positive relationships with team members, clients, employees, brokers, and carriers.

We aim for excellence in everything we do, which means being accurate, on-time, and responsive to our customers’ needs, whether through enrollment support, phone calls, email communication, documentation, or follow-up.

We value individuals who can assess situations, ask thoughtful questions, identify next steps, and help resolve issues with professionalism and care.

We invest in our people and encourage them to deepen their skillsets and broaden their abilities. We value individuals who are eager to take initiative, share knowledge, and support the success of the team.

• Serve as a lead specialist and subject matter resource for Enrollment Specialists in an in-office setting during the seasonal enrollment period.
• Provide day-to-day support by answering questions, clarifying processes, and helping team members navigate enrollment-related situations.
• Assist with training and knowledge sharing, especially when there are system updates, client-specific requirements, or process changes.
• Support Enrollment Specialists by sharing best practices, reinforcing quality standards, and helping troubleshoot routine and moderately complex issues.
• Handle or assist with escalated enrollment questions or situations that require strong attention to detail, empathy, and clear communication.
• Embody Milliman’s values at every touchpoint by demonstrating accuracy, responsiveness, collaboration, and proactive support.
• Review survey feedback and employee enrollment documentation to help identify common questions, process gaps, or opportunities for improvement.
• Help identify gaps and potential enrollments where applications have not been processed.
• Help identify gaps or issues with binder and autopay setup.
• Assist with organizing daily work and prioritizing tasks to help support timely completion of enrollment activities.
• Support new client onboarding preparation by gathering information from internal Account Management and Consulting teams and helping the team understand client-specific enrollment needs.
• Communicate recurring questions, workflow concerns, or process improvement ideas to the appropriate internal partners.
• Collaborate with cross-functional teams to support operational efficiency and a positive enrollment experience.
• Help navigate delicate or complex situations with employees, employers, brokers, or insurance carriers when empathy and communication are critical.
• Escalate issues appropriately when additional review or decision-making is needed.

• A minimum of a high school diploma or equivalent GED is required for this position, and education will be verified upon an accepted offer of employment
• Candidates are required to have a minimum of 2 years of professional work experience
• Strong communication and listening skills with the ability to build relationships with Enrollment Specialists, brokers, client decision-makers, employees, and insurance carriers.
• Ability to communicate clearly and confidently in situations requiring direct communication.
• Strong enrollment, customer service, or benefits-related knowledge with the ability to serve as a trusted resource for others.
• Ability to guide and support peers in a collaborative, non-managerial capacity.
• Exceptional attention to detail for accurate internal and external documentation.
• Strong problem-solving skills and the ability to evaluate situations, identify next steps, and follow through.
• Self-motivated, enthusiastic, and driven with a positive, can-do attitude.
• Willingness to seek guidance when needed and adapt to changing circumstances.
• Above-average technology skills, including proficiency in CRM software and other tools.
• Previous experience serving as a senior specialist, peer mentor, trainer, quality resource, or subject matter expert in a call center, customer service, benefits, or similar environment is a plus.
• Preferred experience in the health insurance industry, specifically employee benefits and/or personal insurance.
• Previous experience in Customer Success, Advocacy, Relationship Management, or Account Management is a plus.
• Passion for building relationships and thinking creatively to solve problems.
• Strong team player who values collaboration and shared success.
• Resilient, with a positive attitude and the ability to thrive in a fast-paced seasonal environment.
• Naturally curious and eager to learn from peers while embracing innovation and new ideas.
• Flexible, collaborative, dependable, and comfortable serving as a go-to resource for others.
• Availability to work on a seasonal, full-time schedule in office for the duration of the enrollment season.

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