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
The Principal Program Manager is the most senior program management position and responsible for leading and coordinating strategic business initiatives, operational priorities, and cross-functional programs that support the Senior Vice President and the overall business line. They are leaders driving execution through collaboration, operational excellence, and continuous improvement. They are accountable for ensuring business initiatives, operational priorities, and enterprise projects consistently deliver business value, align with business and technical strategy and provide exceptional customer experience for our business partners. This role serves as a strategic partner to the Senior Vice President, leading execution of key business initiatives, operational improvements, and organizational priorities and will work closely with executive leadership, cross-functional business partners, operations, finance, compliance, technology, and external partners.
The Principal Program Manager will organize, coordinate and provide status on strategic initiatives, operational performance, executive priorities, and enterprise projects to ensure delivery of current and future business needs. Collaborates with functional areas for effective use of resources to meet business needs.
What You’ll Do
Develop proactive relationships with senior leaders of supported business units that are built on trust, transparent communication, and a spirit of collaboration
Forecast IT resource requirements and equipment needs based on business units; pipeline of planned projects
Support executive communications, leadership presentations, board materials, and strategic planning activities
Partner with Risk, Compliance, Finance, and Operations to ensure adherence to organizational policies, regulatory requirements, and governance standards
Partner with the Senior Vice President to translate strategic priorities into actionable business plans, business cases, and measurable outcomes
Represent the business line’s priorities across the organization, ensuring stakeholders remain informed, engaged, and aligned throughout strategic initiatives and operational projects
Partner with business leaders and cross-functional teams to remove operational roadblocks, improve processes, and accelerate high-priority business initiatives
Qualifications
Bachelor’s degree in business or technology
10+ years working in a financial services environment with special emphasis on coordinating large cross functional programs and stakeholder management
8+ years of management experience in which one or more of the following has occurred:
Demonstrated high competency in the prioritization of various competing deliveries of efforts
Demonstrated competency in strategic thinking and leadership with strong abilities in relationship management
Experience in managing resources to meet goals across multiple projects
Experience in leading multidisciplinary, high-performance work teams/groups
Demonstrated competency in developing efficient and effective solutions to diverse and complex business operations
Working knowledge of general IT and business operations
Must possess exceptional leadership, time management, facilitation, and organizational skills
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.
#LI-Remote
#LI-JB1
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.
Skills Required
- Bachelor's degree in business or technology
- 10+ years working in a financial services environment coordinating large cross-functional programs and stakeholder management
- 8+ years of management experience (prioritizing competing deliveries, strategic leadership, relationship management)
- Experience managing resources to meet goals across multiple projects
- Experience leading multidisciplinary, high-performance teams
- Demonstrated competency in developing efficient and effective solutions to complex business operations
- Working knowledge of general IT and business operations
- Exceptional leadership, time management, facilitation, and organizational skills
Wintrust Financial Corporation Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Wintrust Financial Corporation and has not been reviewed or approved by Wintrust Financial Corporation.
-
Affordable Benefits — Employer covers a large share of medical premiums, making health coverage comparatively low cost. Plan options are broad and pair with HSA/FSA choices and wellbeing programs.
-
Parental & Family Support — Paid maternity, parental, and adoption leave are structured and fully paid, with backup childcare access through Bright Horizons. Adoption assistance and family support resources further strengthen caregiving support.
-
Retirement Support — A 401(k) with a company match and an employee stock purchase plan provide multiple savings and ownership avenues. Match mechanics and plan access are noted features of the total rewards offering.
Wintrust Financial Corporation Insights
What We Do
Wintrust Financial (Wintrust) is a financial services holding company based in Rosemont, Illinois, with $50 billion in assets. Wintrust engages in the business of providing traditional community banking services, wealth management services, commercial insurance premium financing, mortgage origination and more.
Gallery
