Advanced Program Manager

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.”

The Advanced Program Manager is an experienced program delivery professional responsible for coordinating and executing medium-to-large scale technology initiatives. This role focuses on driving execution across engineering teams while developing stronger program leadership capabilities. This position emphasizes hands-on coordination, structured delivery, and growing influence across cross-functional teams.

The role partners closely with engineering managers, product owners, and architects to ensure delivery commitments are met, risks are managed, and communication is clear. Exposure to .NET, Salesforce, and Java initiatives is common, but deep specialization is not required.

Responsibilities
• Coordinate delivery of multi-team technology initiatives across engineering pods
• Support program planning, including scope definition, timelines, and resource coordination
• Track progress against milestones and ensure alignment across teams
• Identify risks, blockers, and dependencies and escalate as needed
• Facilitate core Agile ceremonies (sprint planning, standups, retrospectives, demos)
• Maintain program tracking artifacts (roadmaps, RAID logs, status reports)
• Communicate program status, risks, and progress to stakeholders and leadership
• Partner with engineering leads to ensure clarity of scope and execution plans
• Assist in managing cross-functional dependencies (engineering, QA, product, operations)
• Contribute to improving delivery processes and team efficiency
• Support production release coordination and post-release monitoring

Skills and Knowledge-
• 4–7 years of program/project management experience in technology environments
• Experience supporting delivery across engineering teams (Agile/Scrum preferred)
• Strong organizational and coordination skills with attention to detail

Technical Exposure (Preferred):
• Familiarity with software development concepts (APIs, integrations, SDLC)
• Exposure to .NET or Salesforce delivery environments
• Awareness of emerging AI initiatives and how they impact engineering workflows

Program Management Capabilities:
• Experience with Agile tools (Jira, Azure DevOps, etc.)
• Basic understanding of dependency management and risk tracking
• Ability to manage competing priorities across multiple workstreams

• Strong communication skills (clear, structured, audience-aware)
• Ability to work in fast-paced environments with evolving requirements
• Collaborative mindset with ability to work across engineering and business teams
• Developing ability to influence without authority

Working Relationships

Internal:
Reports to Program Management or Engineering Leadership
Works closely with engineering managers, product owners, and scrum teams
Coordinates across multiple delivery teams

External:
Limited interaction with vendors or partners, typically supporting senior program managers
May assist in coordination with external resources as needed

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 $110,000.00 - $120,000.00, 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.