Sales Development Representative
Posted Sep 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
Tell me about a time you had to keep going after hearing no many times.
What they are checking: Whether they have the resilience that daily prospecting requires.
Describe a time you learned something difficult quickly. How did you do it?
What they are checking: Whether they can absorb the training program and product knowledge fast.
How do you organize your day when you have a long list of accounts to work?
What they are checking: Whether they can manage their time and stay disciplined without close supervision.
Tell me about a goal you set and hit that took sustained effort.
What they are checking: Whether they are driven by goals, which is how SDR success is measured.
This role is in the Chicago office every day. How does that fit how you like to work?
What they are checking: Whether they are realistic about the in-office expectation and will thrive with it.
What would you do
Pitch me Stripe as if I'm a small online business owner you just reached on the phone.
What they are checking: Whether they can open a cold conversation clearly and focus on the prospect's needs.
A prospect says they're happy with their current payments provider. What do you say next?
What they are checking: Whether they can handle an objection with curiosity rather than pushing harder.
How would you use feedback from a mentor or manager after a call that went badly?
What they are checking: Whether they welcome coaching and act on it, which the mentor program depends on.
About the work
In your own words, what does Stripe do and why would a business choose it?
What they are checking: Whether they did their homework and can explain the company simply.
How would you research a company before reaching out to them?
What they are checking: Whether they personalize outreach instead of sending the same message to everyone.
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Practice this out loudThe full job description
As published by Stripe.