Insurance Program Manager Jobs in Chicago, IL (NOW HIRING)

Wintrust provides community and commercial banking, specialty finance and wealth management services through its 16 bank charters and nine non-bank businesses. Wintrust delivers the sophisticated solutions of a large bank while staying true to the relationship-focused, personalized service of our community banking roots. We serve clients in all 50 states with more than 200 branch banking locations in Illinois, southwestern Florida, northwestern Indiana, west Michigan and southern Wisconsin and commercial banking offices in Chicago, Denver, Milwaukee, Grand Rapids, Mich., and in key branch banking locations throughout Illinois. Our people are the heart of our business and we are proud to rank consistently as a top place to work. Wintrust is a $66 billion financial institution based in Rosemont, Illinois, and listed on the NASDAQ Global Select Market under the symbol "WTFC."

Why join us?

• An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 12 years) and Employee Recommended award by the Globe & Mail (past 6 years)

• Competitive pay and discretionary or incentive bonus eligible

• Comprehensive benefit package including medical, dental, vision, life, a 401k plan with a generous company match and tuition reimbursement to name a few

• Promote from within culture

Why join this team?

• This position has the opportunity to interface with and have a positive impact on multiple areas of Wintrust's business

• We hold ourselves accountable to high standards, share wins, operate ethically, and have fun

Position Overview

This role ensures structured execution of data programs aligned to regulatory, risk, modernization and business transformation priorities.

The Program Manager drives delivery excellence by setting delivery standards, builds and nurtures high-performing teams, and ensures disciplined execution across a complex, regulated environment. This role will be responsible for leading and delivering complex, cross-functional data initiatives across the enterprise.

What You'll Do

• Program Delivery & Execution: Own and lead end-to-end delivery of enterprise data initiatives

• Risk Alignment: monitor regulatory commitments and remediation timelines; develop and manage integrated program plans, milestones, dependencies, risks, and financials

• Data Strategy Alignment: translate enterprise data initiatives into executable roadmaps

• Team Leadership & Capability Development: lead and manage a team of program managers, delivery leads, project managers; coach and develop team members into program managers

• Financial and Resource Management: manage program budgets for data management (Capex/Opex) and resource allocation; identify capacity gaps and optimize team utilization

• Ensure overall compliance with the Enterprise Project Management Office's project governance framework

• Other tasks as needed

Qualifications

• Master's degree or MBA highly preferred or equivalent experience

• 10+ years of program management experience preferably in large banking or financial services

• Proven experience leading large scale data, regulatory, or transformation programs

• Strong financial acumen (budget tracking, business case tracking)

• Executive-level communication skills along with strong understanding of the data management landscape, experience operating in regulated environments, and ability to manage matrixed teams

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 $117,000.00 - $158,000.00, along with eligibility to earn an annual bonus. 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.