JobsAdvocate Health

Sales Representative - Healthcare

Advocate Health · Milwaukee, WI

Posted Sep 1, 2026 · We last checked this listing on Sep 20, 2026

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Likely interview questions for this role

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

Behavioral

Walk me through a time you brought in a new employer or broker account from scratch. How did you find them and what did the sales cycle look like from first call to signed contract?

whether the candidate has real experience running a full B2B sales cycle, not just managing warm leads

Tell me about a proposal you built where you had to translate a client's technical or benefits needs into pricing and terms they could actually say yes to.

ability to construct client-specific proposals involving cost analysis, a core listed duty

Give me an example of an account where something went wrong operationally, maybe a service issue or a billing problem, and the client came to you upset. What did you do?

how they handle the investigate-and-correct account issues part of the job under pressure

Tell me about a sale you lost. What happened and what would you do differently now?

self-awareness and whether they learn from failure rather than just recounting wins

Describe a presentation you gave to a group that included both decision-makers and skeptics in the room. How did you read the room and adjust?

presentation skill and adaptability across varied audiences, which the posting explicitly calls out

Tell me about a time you had to work with internal teams, like marketing or operations, to get a deal implemented after the sale was signed.

collaboration skills since the role explicitly requires coordinating internal stakeholders and paperwork for implementation

Technical

What's your process for building out a prospect list and pricing model for a new territory or market segment?

whether they understand the analytical groundwork behind territory development, not just relationship charm

What do you know about how health systems like Aurora work with employer groups and insurance brokers, and how is selling into that world different from selling other products or services?

depth of actual healthcare or health insurance sales knowledge versus generic sales background

Situational

Say you've got a broker who's been a strong partner for years, and suddenly they start steering business to a competing health system. What do you do first?

account retention instincts and whether they escalate or investigate before reacting emotionally

How would you plan your first 90 days covering the Greater Milwaukee territory, given you're doing weekly travel to see employers and brokers in person?

whether they can self-manage a remote, travel-heavy territory without close supervision

How do you keep a long list of existing accounts warm and growing while also chasing new business, especially when your calendar is already full of employer and broker visits?

prioritization skills across hunting and farming responsibilities

If a client asked for a discount or contract term you knew wasn't standard, how would you handle that conversation while still trying to close the deal?

negotiation judgment and whether they protect margin and policy while staying client-focused

Practice this interview out loud.

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The full job description

As published by Advocate Health.

Department: 13387 Enterprise Corporate - Managed Health Strategy Status: Full time Benefits Eligible: Yes Hou rs Per Week: 40 Schedule Details/Additional Information: Full-time, dayshift from 8:00am-5:00pm with some flexibility upon request. This is a remote position for WI or IL region, that requires weekly travel within the Greater Milwaukee territory to call on employers and brokers. Pay Range: $33.05 - $49.60 Major Responsibilities: • Performs the complete sales process: prospecting, developing the proposal, closing the sale with clients, and maintaining client relationships. Works to grow assigned service or program market share and enhance Aurora's image in highlighted markets or with specific employers. • Attracts new business through cold calls, referrals, inquiries, incoming calls, or trade shows. Follows up on interest generated from prospective clients within defined territories. • Participates in the development of territories, which includes the following: developing prospect databases, developing pricing models, communicating to prospects and clients, and participating in the implementation of new products and services. • Collaborates with internal stakeholders and offers input on planning, developing and implementing strategies that create a positive return on investment throughout defined market areas. • Develops proposals specific to clients needs including the cost components and analysis of the technical requirements of the client. Coordinates the appropriate paperwork and communication for new and extended contracts. • Manages the growth and maintenance of existing accounts. Keep clients informed of all technology changes and improvements. • Investigates and corrects all issues with accounts pertaining to services, products, and operational issues. • Participates in the development of marketing resources including: folders and inserts, brochures, flyers, web site materials, etc. Contributes to the development of other sales materials. Licensure, Registration, and/or Certification Required: • None Required. Education Required: • Bachelor's Degree (or equivalent knowledge) in Marketing or related field. Experience Required: • Typically requires 3 years of experience in sales that includes experiences in developing client relationships, implementing business and sales/marketing plans, and product promotion. Preferred Experience : • 6-7 or more years of experience in sales in the healthcare space that includes experiences in developing client relationships, implementing business and sales/marketing plans, and product promotion. • Previous sales experience for a health system. • Previous sales experience in health insurance or health insurance broker. Knowledge, Skills & Abilities Required: • Excellent consultative and problem solving skills. • Excellent sales related skills such as: executing sales plans, relationship building, product promotion, achieving goals/targets and a demonstrated ability to close sales. • Excellent interpersonal and communication skills, ability to effectively deliver professional and engaging presentations for a variety of audiences. • Proficient in the use of Microsoft Office Suite or similar products, and electronic mail. • Excellent organization and prioritization skills, ability to effectively manage multiple demands. Physical Requirements and Working Conditions: • Position requires travel, may be exposed to severe road and weather hazards. • Generally exposed to a normal office environment. • Operates all equipment necessary to perform the job. This job description indicates the general nature and level of work expected of the incumbent. It is not designed to cover or contain a comprehensive listing of activities, duties or responsibilities required of the incumbent. Incumbent may be required to perform other related duties. Our Commitment to You: Advocate Health offers a comprehensive suite of Total Rewards: benefits and well-being programs, competitive compensation, generous retirement offerings, programs that invest in your career development and so much more – so you can live fully at and away from work, including: Compensation • Base compensation listed within the listed pay range based on factors such as qualifications, skills, relevant experience, and/or training • Premium pay such as shift, on call, and more based on a teammate's job • Incentive pay for select positions • Opportunity for annual increases based on performance Benefits and more • Paid Time Off programs • Health and welfare benefits such as medical, dental, vision, life, and Short- and Long-Term Disability • Flexible Spending Accounts for eligible health care and dependent care expenses • Family benefits such as adoption assistance and paid parental leave • Defined contribution retirement plans with employer match and other financial wellness programs • Educational Assistance Program Note: Eligibility for programs listed above may depend on your FTE or status (e.g., full-time, part-time, per diem, temporary, etc.); please ask a Recruiter for more information during an interview. About Advocate Health  Advocate Health is the third-largest nonprofit, integrated health system in the United States, created from the combination of Advocate Aurora Health and Atrium Health. Providing care under the names Advocate Health Care in Illinois; Atrium Health in the Carolinas, Georgia and Alabama; and Aurora Health Care in Wisconsin, Advocate Health is a national leader in clinical innovation, health outcomes, consumer experience and value-based care. Headquartered in Charlotte, North Carolina, Advocate Health services nearly 6 million patients and is engaged in hundreds of clinical trials and research studies, with Wake Forest University School of Medicine serving as the academic core of the enterprise. It is nationally recognized for its expertise in cardiology, neurosciences, oncology, pediatrics and rehabilitation, as well as organ transplants, burn treatments and specialized musculoskeletal programs. Advocate Health employs 155,000 teammates across 69 hospitals and over 1,000 care locations, and offers one of the nation’s largest graduate medical education programs with over 2,000 residents and fellows across more than 200 programs. Committed to providing equitable care for all, Advocate Health provides more than $6 billion in annual community benefits.

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