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This position has closed. Humana removed this listing from their careers page on Oct 6, 2026. The interview prep below is still useful, and there are similar open roles at the bottom of this page.

Medicare Sales Field Agent

Humana · Milwaukee, WI · $31,800–$123,800 a year · Full time

Posted Aug 5, 2026 · We last checked this listing on Oct 5, 2026

Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you built trust with a customer who was skeptical of salespeople.

What they are checking: Whether they earn trust through honesty and patience, which matters with older adults wary of sales pitches.

Tell me about a time you missed a sales goal. What did you do next?

What they are checking: Whether they own results and adjust their approach rather than blaming the market.

You'd work on a team of 8 to 12 agents. How do you balance competing for sales with helping your teammates?

What they are checking: Whether they can be self-driven while still sharing what works with a collaborative team.

What would you do

This is a field role built on grassroots, face-to-face connections. How would you build a pipeline in your territory in Chicago or Milwaukee?

What they are checking: Whether they have a real plan for community events, referrals and local partners instead of waiting for leads.

A prospect's doctor isn't in the plan's network. What do you do?

What they are checking: Whether they put the person's needs first, even if it means not making the sale.

How do you handle the Annual Enrollment Period when everyone wants an appointment at once?

What they are checking: Whether they can manage a heavy seasonal workload and still give each person a careful review.

How would you explain Life, Dental, Vision and Prescription coverage without overwhelming a new client?

What they are checking: Whether they can match extra products to real needs instead of piling on offerings.

How do you stay in touch with clients after the sale so they stay with you year after year?

What they are checking: Whether they see service after enrollment as part of the job, which drives retention and referrals.

About the work

Walk me through how you'd explain the difference between Original Medicare and a Medicare Advantage plan to someone turning 65.

What they are checking: Whether they understand Medicare basics well enough to educate clearly rather than just sell.

What rules do you know of that limit how Medicare plans can be marketed to beneficiaries?

What they are checking: Whether they are aware CMS marketing rules exist, such as limits on unsolicited contact, and respect compliance.

Practice this interview out loud.

Offer builds a real interview for this exact role at Humana from your resume and this job description, asks the questions one at a time, and tells you what landed. The first one is free.

Practice this out loud

The full job description

As published by Humana.

Become a part of our caring community With over 10 million sales interactions annually, Humana understands that while great products are important, it’s the quality of our service that truly defines us. We know that when our members and prospects have delightful and memorable experiences, it strengthens their connection with us and enables us to put their Health First. After all, a health services company that has multiple ways to improve the lives of its customers is uniquely positioned to put those customers at the center of everything it does. The MarketPoint Career Channel Team is looking for accomplished Medicare Sales Field Agents. This is a field-based role, and you must live in the designated territory to serve their local community. As part of a collaborative team of 8–12 Medicare Sales Field Agents, you'll work under the guidance of a Senior Manager and Regional Director who are committed to your success. Together, you will help bring Humana's strategy to life: Deliver on the fundamentals, differentiate through exceptional service, and grow by expanding our reach and influence. What You'll Do in This FIELD-based Role: • Deliver: Build trust and educate individuals on Humana's Medicare Advantage plans and additional offerings like Life, Dental, Vision, and Prescription coverage. • Differentiate: Create meaningful, face-to-face connections through grassroots marketing, community events, and in-home visits—providing a personalized experience that sets Humana apart. • Grow: Drive self-generated sales, meet performance goals, and expand Humana's presence in the market by becoming a valued resource and building relationships in your community. Benefits include: • Medical, Dental, Vision, and a variety of other supplemental insurances • Paid Time Off (PTO) and Paid Holidays • 401(k) retirement savings plan with a company match • Tuition reimbursement and/or scholarships for qualifying dependent children Use your skills to make an impact Required Qualifications: • Active Health Insurance License required or ability to obtain. • Must reside in the assigned territory as listed in this job posting. • Comfortable with daily face-to-face interactions in prospective members' homes, at community-based events and engaging with the community through service, retail environment, organizations, volunteer work, or local events. • Valid state driver's license and proof of personal vehicle liability insurance meeting at least 25/25/10 coverage limits (or higher, based on state requirements). Preferred Qualifications: • Active Life and Variable Annuity Insurance License. • Background in selling Medicare products. • Experience in public speaking or delivering presentations to groups. • Background in supporting Value Based Care organizations. • Familiarity with Salesforce or similar CRMs • Associate or bachelor’s degree. • Bilingual in English and an additional language, with the ability to speak, read, and write fluently in both languages. Additional Information Driving Statement: This role is part of our company's driver safety program and therefore requires an individual to have a valid state driver's license and are expected to maintain personal vehicle liability insurance. State driver's license is subject to driver license validation and MVR review. Individuals must carry vehicle insurance in accordance with their residing state minimum required limits, or $25,000 bodily injury per person/$25,000 bodily injury per event /$10,000 for property damage or whichever is higher. Language Proficiency Assessment: Any Humana associate who speaks with a member in a language other than English must take a language proficiency assessment, provided by an outside vendor, to ensure competency. Applicants will be required to take the Interagency Language Rating (ILR) test as provided by the Federal Government. Schedule: Meeting with members requires appointments and/or event times that may vary at night and weekends. Flexibility is essential to your success. Training: The first five weeks of employment and attendance are mandatory. #medicaresalesrep Work at Home Requirements: To ensure Home or Hybrid Home/Office employees’ ability to work effectively, the self-provided internet service of Home or Hybrid Home/Office employees must meet the following criteria: At minimum, a download speed of 25 Mbps and an upload speed of 10 Mbps is required; wireless, wired cable or DSL connection is suggested. In certain roles, the minimum recommended internet speed required by Humana may not be sufficient for business needs. Humana reserves the right to require associates to upgrade their internet service if necessary. Work from a dedicated space lacking ongoing interruptions to protect member PHI / HIPAA information. Travel: While this is a remote position, occasional travel to Humana's offices for training or meetings may be required. Scheduled Weekly Hours 40 Pay Range The range below reflects a good faith estimate of total compensation for full time (40 hours per week) employment at the time of posting. This compensation package includes both base pay and targeted commission pay. The pay range may be higher or lower based on geographic location. Actual earnings will vary based on individual performance, with the base salary and commission structure aligned with company policies and applicable pay transparency requirements. $31,800 - $123,800 per year Description of Benefits Humana, Inc. and its affiliated subsidiaries (collectively, “Humana”) offers competitive benefits that support whole-person well-being. Associate benefits are designed to encourage personal wellness and smart healthcare decisions for you and your family while also knowing your life extends outside of work. Among our benefits, Humana provides medical, dental and vision benefits, 401(k) retirement savings plan, time off (including paid time off, company and personal holidays, paid parental and caregiver leave), short-term and long-term disability, life insurance and many other opportunities. About us About Humana: Humana Inc. (NYSE: HUM) is a leading U.S. healthcare company. Through our Humana insurance services and our CenterWell healthcare services, we make it easier for the millions of people we serve to achieve their best health – delivering the care and service they need, when they need it. These efforts are leading to a better quality of life for people with Medicare and Medicaid, families, individuals, military service personnel, and communities at large. Learn more about what we offer at Humana.com and at CenterWell.com. ​ Equal Opportunity Employer It is the policy of Humana not to discriminate against any employee or applicant for employment because of race, color, religion, sex, sexual orientation, gender identity, national origin, age, marital status, genetic information, disability or protected veteran status. It is also the policy of Humana to take affirmative action, in compliance with Section 503 of the Rehabilitation Act and VEVRAA, to employ and to advance in employment individuals with disability or protected veteran status, and to base all employment decisions only on valid job requirements. This policy shall apply to all employment actions, including but not limited to recruitment, hiring, upgrading, promotion, transfer, demotion, layoff, recall, termination, rates of pay or other forms of compensation and selection for training, including apprenticeship, at all levels of employment.