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VP, Business Strategy - WLF

Wintrust · Rosemont, IL · $98,000–$132,000 a year · Full time

Posted Aug 3, 2026 · We last checked this listing on Oct 6, 2026

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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 strategic initiative you took from analysis to launch.

What they are checking: Whether they can carry a strategy through execution, not just produce a deck.

You manage the process efficiency and strategy administration team. How do you lead them?

What they are checking: Whether they can manage people while also doing high-level analysis.

Tell me about a time you found an inefficiency in operations and fixed it.

What they are checking: Whether they can evaluate operations with departments and drive improvements.

How do you build reports and presentations that busy executives actually read?

What they are checking: Whether they lead with the insight and decision rather than burying it in data.

What would you do

How do you decide which strategic initiatives get priority when resources are limited?

What they are checking: Whether they use clear criteria like return, risk and effort to make tradeoffs.

How do you present findings to an EVP who disagrees with your conclusion?

What they are checking: Whether they can defend analysis with evidence while staying open to other views.

About the work

How would you explain life insurance premium finance and who it serves?

What they are checking: Whether they understand the borrowers, planning structures and collateral behind the business.

What market research would you do to support Wintrust Life Finance's strategic plan?

What they are checking: Whether they can identify relevant data on carriers, advisors, wealth trends and competitors.

How would you measure whether a new product or process change in premium finance is working?

What they are checking: Whether they define success metrics before launch and track them honestly.

What risks do you see in life premium finance when interest rates rise?

What they are checking: Whether they understand how rate changes affect borrower costs, collateral and policy performance.

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The full job description

As published by Wintrust.

As the largest life insurance premium finance company in the country, Wintrust Life Finance provides customized financing solutions to qualified borrowers seeking to finance their life insurance premiums. Our financing solutions have supported numerous planning structures, including traditional wealth transfer, key-man insurance, buy-sell arrangements, split dollar arrangements, term alternatives, charitable giving, income replacement strategies, and more. Wintrust Life Finance is a subsidiary of Wintrust, a financial services company with more than $66 billion in assets. The WLF VP, Business Strategy , is responsible for collaborating with key stakeholders in the analysis, formulation and execution of WLF’s strategic plan. Key aspects of this position focus on completing life premium finance market research, analysis, reporting, strategic initiative development, project & product management, and delivering regularly scheduled reports and presentations in collaboration with department EVP. What You'll Do Strategy & Strategic Planning: • Manage WLFs process efficiency and strategy administration team • Collect and analyze premium finance data related to strategic plan and generate insights to initiate strategic development activities • Complete regularly scheduled market research in support of strategic plan • Collaborate with departments to evaluate operations to identify growth and development opportunities • Monitor and evaluate the performance of the company’s strategies, initiatives, and objectives and report findings to executive leaders • Help drive decision making resulting in medium- and long-term process improvements • Proactively present business findings, projections and make recommendations to department EVP and other leaders as appropriate • Support EVP in developing and communicating WLFs strategic initiatives, including but not limited to presentations, financial reports, and models in both written and verbal formats • Lead effective, efficient meetings with clients, prospects, and WLFs Strategic Initiative Owners to drive strategic plan efforts • In conjunctions with department EVP, act as an internal dot connector, working with project managers to ensure internal resources are collaborative and projects/work streams are on time and in line with expectations • Partner with WLFs Strategic Initiative Owners, Wintrust’s ePMO and Wintrust Oversight teams (ePMO, TPRM, IC, CC, IPA, ASRB and InfoSec) to drive strategic level project approval and implementation Product Development & WLF Business Line Support: • Drive internal understanding of key customer personas and engage with clients/prospects to better understand workflows. Synthesize learnings to internal stakeholders to drive and facilitate loan growth • Partner with Sales, Sales Leadership and Client Success teams to define, enhance, track and drive product adoption • Through the lens of the Strategic Plan build Product Level KPIs to define, monitor and manage success • Support optimization modeling and process planning in collaboration with team level management, outside sales and internal stakeholders. Evaluate premium tiers for client/prospects, calculate quote conversation ratios, average down payments, installments, and price to deliver actionable recommendations in identifying growth opportunities Foster a culture of collaboration and process improvement: • Look for opportunities, identify gaps and scale efficiencies and new ways of working across multiple projects and environments • Influence and facilitate the creation of long-term relationships with other departments and vendors • Source data to make compelling and tangible recommendations of a future state for the organization • Leverage relationships and organizational values to prioritize outcomes effectively • Employ practical methods and action steps to move the organization toward the strategic vision • Help Identify obstacles to transformation and challenge conventional thinking Qualifications • 10-15 years of experience in the Financial Industry • Premium Financial experience preferred • Experience owning a strategic initiative from concept to completion • Bachelor's Degree required • MBA Preferred • Onsite position Compensation The estimated salary for this role is $98,000 - $132,000 along with eligibility to earn an annual bonus. Actual pay rate may vary based on several factors, such as a candidate’s qualifications, skills and experience 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 #LI-ONSITE #LI-LR1 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.

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