Seasonal Enrollment Specialist Lead

Milliman, Inc; Omaha (NE); On-site; USD 40,000 - 66,000; Full time

Benefits offered by this job

EAP (Employee Assistance Program)

401(k) plan with company match

Paid Time Off (PTO)

Transit/parking pre-tax benefits

Job summary

Milliman in Omaha, Nebraska is seeking a dedicated enrollment support lead for the seasonal period. The role centers on guiding Enrollment Specialists, answering complex questions, and ensuring accurate enrollment processing.

You will train peers on new processes, share best practices, and escalate higher‑level issues with empathy while upholding Milliman's standards for quality and client service.

Qualifications

• Minimum of a high school diploma or GED; education verified on offer
• Minimum of 2 years of professional work experience
• Strong communication and listening skills to build relationships with Enrollment Specialists, brokers, clients, employees, and carriers
• Ability to communicate clearly and confidently in direct situations
• Experience in enrollment, customer service, or benefits knowledge preferred
• Senior specialist/mentor/trainer experience in call center or customer service is a plus
• Experience in health insurance employee benefits is a plus
• Strong teamwork and collaboration skills; resilient in fast-paced seasonal environment
• Curiosity and willingness to learn and adapt to new ideas
• Comfort with CRM tools and technology

Responsibilities

• Serve as a lead specialist and resource for Enrollment Specialists during the in-office seasonal enrollment period
• Provide day-to-day support by answering questions and clarifying processes
• Help with training and knowledge sharing during system updates or client requirements
• Support Enrollment Specialists by sharing best practices and troubleshooting issues
• Handle or assist with escalated enrollment questions requiring attention to detail and empathy
• Demonstrate Milliman values through accuracy, responsiveness, and collaboration
• Review survey feedback and enrollment documentation to identify questions or process gaps
• Identify gaps or potential enrollments where applications have not been processed
• Assist with binding and autopay setup issues
• Organize daily work and prioritize tasks to support timely enrollment activities
• Assist with onboarding preparation by gathering information from internal teams
• Communicate recurring questions or workflow concerns to internal partners
• Collaborate with cross-functional teams to improve operational efficiency
• Navigate delicate situations with employees, employers, brokers, or carriers with empathy
• Escalate issues when additional review is needed

Skills

Relationship building

Communication

Problem solving

Mentoring

Training

Attention to detail

Empathy

Team player

Adaptability

Education

High school diploma or GED

Tools

CRM software

Job description

We're looking for:

Relationship builders. 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.

Confident professionals. 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.

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

Future leaders. 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.

Duties & 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 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.

Skills, Qualifications, and Experience:

• 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.

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. Much of our success depends on our employees and our culture, which recognizes and rewards employees for the value they bring to our business in general and our clients in particular.

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.

Seasonal Employment Details

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.

Compensation

Compensation for this seasonal role will be discussed during the hiring process and will be based on factors such as experience, qualifications, and skills.

Benefits

• Employee Assistance Program (EAP) - Confidential support for personal and work‑related challenges.
• 401(k) Plan - When an employee reaches 1,000 hours worked within 12 consecutive months, they become eligible for a 401(k) plan that includes a company matching program and profit‑sharing contributions.
• Paid Time Off (PTO) - Begins accruing on the first day of work; Interns, Temporary, and Seasonal Employees will earn PTO each pay period, based on 1 hour for every 30 hours worked.
• Transportation - Pre‑tax savings for eligible transit and parking expenses.

Equal Opportunity

All qualified applicants will receive consideration for employment, without regard to race, color, religion, sex, sexual orientation, national origin, disability, or status as a protected veteran.

Equal Opportunity Employer/Protected Veterans/Individuals with Disabilities

This employer is required to notify all applicants of their rights pursuant to federal employment laws.

For further information, please review the Know Your Rights notice from the Department of Labor.