Sales Representative - Healthcare
Posted Sep 1, 2026 · We last checked this listing on Sep 20, 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.
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
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Practice this out loudThe full job description
As published by Advocate Health.
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