Division President - East Coast
Posted Jul 17, 2026 · We last checked this listing on Oct 4, 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
FIRST Insurance Funding grows through agents, brokers and national accounts. Walk me through how you've grown premium finance or similar business in a region.
What they are checking: Whether they have a proven track record growing production through agency and broker relationships.
Tell me about a sales team you built or turned around. What changed?
What they are checking: Whether they can show real leadership results, with specifics about people and process.
What would you do
How do you balance organic growth from existing agencies with landing new business?
What they are checking: Whether they know where growth comes from and can direct the team's effort to both.
One of your Area Sales Managers is missing targets two quarters in a row. What do you do?
What they are checking: Whether they can diagnose the cause and coach or make tough decisions fairly.
How would you win a large regional broker that already works with a competitor?
What they are checking: Whether they can build a winning pitch around service, technology and incentives, not just rate.
You're expected to promote other Wintrust lending services. How would you spot those opportunities with agencies?
What they are checking: Whether they think about the broader Wintrust relationship and can cross-sell with care.
How do you manage a team spread across several East Coast states?
What they are checking: Whether they can lead remote teams with structure, travel and regular contact.
About the work
You'd lead Area Sales Managers and 8 to 10 Relationship Managers. How do you set goals and hold them accountable?
What they are checking: Whether they can run a sales organization with clear targets, activity tracking and coaching.
Explain how premium finance works and where the main risks are for the lender.
What they are checking: Whether they understand the product deeply, including cancellation, unearned premium and credit risk.
How do you grow volume without hurting profitability?
What they are checking: Whether they keep margin and credit quality in view, which the posting ties to maximum profitability.
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As published by Wintrust.