Seasonal Enrollment Specialist Lead

About the Role

We are looking for relationship builders who are fanatical about serving our customers and contributing to their success. This role requires strong communication skills to build positive relationships with team members, clients, employees, brokers, and carriers. We value confident professionals who strive for excellence in accuracy, timeliness, and responsiveness to customer needs through enrollment support, phone calls, email communication, documentation, or follow-up. Problem solvers who can assess situations, ask thoughtful questions, and resolve issues with professionalism and care are essential. We invest in our people and encourage them to deepen their skillsets, broaden their abilities, and take initiative to support team success.

Responsibilities

• 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 during 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 requiring 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 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 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.

Requirements

• A minimum of a high school diploma or equivalent GED is required; education will be verified upon an accepted offer of employment.
• 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 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.
• Availability to work on a seasonal, full-time schedule in office for the duration of the enrollment season.

Preferred Qualifications

• 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.
• Experience in the health insurance industry, specifically employee benefits and/or personal insurance.
• Previous experience in Customer Success, Advocacy, Relationship Management, or Account Management.
• 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.

About Milliman

Milliman (www.milliman.com) is an international consulting firm with over 5,100 employees and $1.6 billion in annual revenue. With over 75 years in the consulting business, we have earned an excellent reputation for superior tools and service to our clients. The Omaha Health & Welfare practice was started 25 years ago to serve large employers in the design and administration of their employee benefit insurance plans. Our success depends on our employees and our culture, which recognizes and rewards employees for the value they bring to our business and clients. The atmosphere is business casual with 75 other professionals in an upscale office setting at 180th and Dodge Street in Omaha, Nebraska.

Location

This is an in-office role based in Omaha, Nebraska. Candidates hired in this position will be expected to work onsite at the Milliman Omaha office for the duration of the seasonal assignment.

Schedule

This is a seasonal position designed to support the team during the annual open enrollment period. Employment is expected to last for the duration of the seasonal business need, with schedules and assignment length communicated during the hiring process. The duration of the assignment may be adjusted based on business needs and does not guarantee ongoing employment beyond the assignment period.

Benefits

• Employee Assistance Program (EAP): Confidential support for personal and work-related challenges.
• 401(k) Plan: Eligibility begins after reaching 1,000 hours worked within 12 consecutive months; includes a company matching program and profit-sharing contributions.
• Paid Time Off (PTO): Begins accruing on the first day of work; earn 1 hour for every 30 hours worked.
• Transportation: Pre-tax savings for eligible transit and parking expenses.