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This position has closed. Wintrust removed this listing from their careers page on Oct 6, 2026. The interview prep below is still useful, and there are similar open roles at the bottom of this page.

Division President - East Coast

Wintrust · Remote · $141,000–$190,000 a year · Full time

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.

Practice this interview out loud.

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The full job description

As published by Wintrust.

As one of the largest premium finance companies in the country, FIRST Insurance Funding provides full premium finance services, plus additional services built specifically for agencies. We pride ourselves on the variety of incentive programs, services, and technology we offer. This not only helps grow the agents, brokers, and companies we partner with, but also helps them better serve their clients. FIRST Insurance Funding is a subsidiary of Wintrust, a financial services company with more than $66 billion in assets. Responsible for sales & marketing leadership in several states in the Eastern Region with 6 -7 direct reports. Achieving production growth through organic and new business opportunities. Monitor results and promote other Wintrust lending services. Provide assistance or direct sales on national accounts and larger regional associations and brokers, as directed by EVP and President. What You'll Do • Help grow revenue through organic and new business activities through network of key contacts and directly leading one regional sales team. Work closely with EVP and President to achieve sales and revenue goals, as well as maximum profitability. • Develop team to help grow broker and national associations. Direct reports will include Area Sales Managers, along with 8-10 Relationship Managers. Employee will work closely with EVP and President to drive best practices. • Maintain close relationship with C Suite for top 100 Agents and top 50-100 regional agents with their regions, as directed by EVP to ensure proper coverage. Work directly with RM’s on key relationships when necessary and strategically to grow their territories, with a focus on directly assisting to close new business opportunities. • Execute strategic plans as determined by EVP and President to ensure proper activity levels are met at all locations of all our agent clients. Promote visibility and networking while attending regional and national broker events, in addition to industry partner events, to promote new business opportunities. • Approve new agent programs and revisions to current agent programs. • Manage expenses, monitor sales activates through Salesforce, Power BI and other financial tools. • Act as liaison for Agency Lending and all other Wintrust products Qualifications • 10+ years of experience, premium finance preferred • Travel required • Advanced computer skills and experience with Salesforce Benefits: Medical Insurance • Dental • Vision • Life insurance • Accidental death and dismemberment • Short-term and long-term Disability Insurance • Parental Leave • Employee Assistance Program (EAP) • Traditional and Roth 401(k) with company match • Flexible Spending Account (FSA) • Employee Stock Purchase Plan at 5% discount • Critical Illness Insurance • Accident Insurance • Transportation and Commuting Benefits • Banking Benefits • Pet Insurance Compensation The estimated salary range for this role is $141,000 - $190,000 along with eligibility to earn commission and LTIP. Actual salaries may vary based on several factors, such as a candidate’s qualifications, skills and experience. From our first day in business, Wintrust has been proud to serve a variety of unique communities and people from all walks of life. To build a company that reflects the communities we serve, we believe that fostering a unique and inclusive workplace where everyone feels valued and empowered to succeed will support our ongoing success. Wintrust Financial Corporation, including community banking and financial services subsidiaries, is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, age, national origin, disability, veteran status, genetic information, and other legally protected categories.