VP, Enterprise Project Management

Wintrust Financial Corporation; Rosemont (IL); On-site; USD 141,000 - 190,000; Full time

Benefits offered by this job

Medical Insurance

Dental

Vision

Life Insurance

Disability Insurance

Parental Leave

Employee Assistance Program (EAP)

401(k) with company match

Flexible Spending Account (FSA)

Employee Stock Purchase Plan

Critical Illness Insurance

Accident Insurance

Transportation and Commuting Benefits

Banking Benefits

Pet Insurance

Job summary

Wintrust Financial Corporation, a leading financial services company based in Rosemont, IL, is seeking a Vice President of Enterprise Project Management to lead the organization’s project management function. You will translate strategy into executable programs, ensuring investments align with business priorities and deliver measurable results on time and within budget.

You will collaborate with executive leadership, sponsors, and business leaders to prioritize initiatives, establish governance,

Qualifications

• 10+ years of related experience in project management or a similar role.
• Proven ability to lead large-scale enterprise programs and cross-functional teams.
• Strong ability to influence sponsors and drive outcomes.

Responsibilities

• Lead enterprise projects and programs, ensuring delivery aligns with strategic priorities, scope, and budget.
• Partner with executive sponsors to prioritize initiatives and drive timely decisions.
• Establish and maintain project governance, delivery standards, and reporting practices.
• Provide executive dashboards and portfolio reporting that highlight progress, financial performance, resources, and risks.
• Lead, coach, and develop project management professionals, fostering accountability and growth.
• Coordinate with Technology, Business Process Improvement, and Change Management to support readiness and measurable benefits.
• Continuously improve ePMO processes, tools, and practices to simplify delivery.

Skills

Project leadership

Stakeholder management

Executive communication

Governance

Team leadership

Education

Bachelor’s degree and/or PMP Certification preferred

Job description

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?

• Be a member of a small, but high-performing, tight knit group of peers. You’ll get to learn from other experienced professionals.
• Opportunities to work on high-impact projects. You will have the opportunity to work on projects that have a significant impact on Wintrust’s bottom line.
• Work with a diverse team. The enterprise project management team is made up of people from different backgrounds and experiences.
• Make a difference. You will have an opportunity to make a real difference in the company and the lives of its customers.
• Learn and grow your skills. The team is constantly learning and evolving, and they are always willing to share their knowledge with others.

Position Overview

The Vice President of Enterprise Project Management leads the organization’s project management function, ensuring strategic initiatives are prioritized, governed, and successfully delivered. This role partners with executive leadership to translate strategy into executable programs, ensuring investments align with business priorities and deliver measurable results on time and within budget.

What You’ll Do

• Lead enterprise projects and programs, ensuring delivery aligns with strategic priorities and achieves results on time, within scope, and within budget.
• Partner with executive sponsors and business leaders to prioritize initiatives, manage dependencies, resolve barriers, and drive timely decisions.
• Establish and maintain project governance, delivery standards, and consistent practices for planning, reporting, risk management, and change control.
• Provide executive dashboards and portfolio reporting that highlight delivery progress, financial performance, resource capacity, and risks requiring escalation.
• Lead, coach, and develop project management professionals, fostering accountability, collaboration, employee engagement, and career growth.
• Coordinate with Technology, Business Process Improvement, and Change Management to support business readiness, operational handoffs, and measurable business benefits.
• Continuously improve ePMO processes, tools, and practices to simplify delivery, reduce administrative effort, and prevent recurring issues.

Qualifications

• 10+ years of related experience; Bachelor’s degree and/or PMP Certification preferred
• Proven project leadership and success in managing large scale projects/ programs across the Enterprise and within an individual lines of business
• Demonstrated ability to influence and coach sponsors and other key stakeholders to drive and deliver outcomes
• Experience in developing, optimizing and executing Enterprise-wide project management strategies, methodologies, frameworks and governance practices
• Experience in leading and managing teams and driving employee engagement
• Strong executive communication and influence; financial services or regulated industry experience preferred.
• Prior ePMO leadership and financial services or regulated industry preferred

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 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.