Pet Insurance Sales Associate - Chicago, IL
Posted Aug 25, 2026 · We last checked this listing on Oct 6, 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
Walk me through a time you had to sell something face to face to someone who wasn't expecting to be sold to. What did you do in the first thirty seconds?
What they are checking: whether the candidate can handle cold, unscripted, in-person prospecting rather than relying on inbound or scheduled leads
Tell me about your experience working in an animal care role. What did a typical day look like and how did that prepare you to talk with pet parents about insurance?
What they are checking: whether the 3-5 years of animal care experience is real and translates into credibility with pet parents, not just a checkbox
This role expects you to work Friday through Sunday because that's when it's most lucrative. How do you feel about that schedule and how have you managed a non-traditional workweek before?
What they are checking: genuine willingness to accept the peak-hours schedule rather than discovering later it's a dealbreaker
Tell me about a time a partner or client relationship started rocky and you turned it around.
What they are checking: relationship-building skill with shelter staff, who are gatekeepers to the pet parents this role needs to reach
Tell me about a stretch where you didn't hit a sales goal. What happened and what did you change?
What they are checking: honesty about setbacks and whether they self-correct or make excuses
Tell me about a time you had to manage your own expenses or submit reports on a deadline without someone reminding you.
What they are checking: reliability on the administrative side of a mostly unsupervised, field-based role
What would you do
Say you're set up at a shelter partner location and it's a slow Saturday, foot traffic is low. What do you do with your time instead of just waiting at the table?
What they are checking: self-direction and hustle during unproductive stretches, since the role has no manager standing over the agent
A pet parent tells you they already have coverage through another provider and it's cheaper. How do you handle that conversation?
What they are checking: ability to sell against competitors on value rather than just price, and product knowledge of Fetch versus competitors
You notice a shelter partner seems less enthusiastic about having you on-site than they used to be. What would you do to figure out why and fix it?
What they are checking: proactive account management and reading a partner relationship before it becomes a lost placement
This job requires regional driving and some national air travel to shelters. What's your actual availability and comfort level with that kind of travel?
What they are checking: realistic fit with the travel demands before it becomes friction after hire
About the work
How would you explain what makes Fetch's coverage different from a typical pet insurance plan to someone who's never thought about pet insurance before?
What they are checking: actual product knowledge and ability to communicate it simply, not memorized talking points
How do you keep track of prospects and follow-ups when you're moving between locations all day instead of sitting at a desk?
What they are checking: discipline around CRM data entry and administrative follow-through, which the posting flags as a real requirement
Where do you stand on getting a Property and Casualty license, and have you looked into what that process involves in Illinois?
What they are checking: whether the candidate has done basic homework and is genuinely ready to obtain licensing within 30 days
Practice this interview out loud.
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Practice this out loudThe full job description
As published by Fetch.