Advanced Program Manager

Wintrust Financial Corporation; Rosemont (IL); Hybrid; USD 85,000 - 110,000; Full time

Benefits offered by this job

Medical Insurance

Dental and Vision

Life Insurance

401(k) with company match

Tuition reimbursement

Job summary

Wintrust Financial Corporation is seeking an Advanced Program Manager to lead intelligent automation initiatives. You will own the end-to-end roadmap for RPA, AI/ML, and IDP, guiding the team and collaborating with stakeholders to deliver value while ensuring regulatory compliance.

The role is full-time, based at the Rosemont, IL office, with a hybrid work schedule and opportunities to interface across multiple business units.

Qualifications

• Familiarity with intelligent automation tools (e.g. RPA, AI/ML)
• 3–5 years in financial services
• Working knowledge of agile methodology, techniques, and frameworks to deliver solutions
• 3–5 years of progressive experience in related fields (e.g. project management, business analyst, etc.)
• Bachelor’s degree or equivalent.

Responsibilities

• Develop and manage end-to-end automation roadmaps across RPA, AI/ML, and IDP.
• Coordinate with business sponsors and technology teams to deliver scalable automation solutions.
• Lead and mentor teams to ensure backlog prioritization and on-time delivery.
• Collaborate with Scrum Master to translate roadmaps into delivery cycles.
• Track progress and present status reports; drive continuous improvement and automation-first thinking.

Skills

RPA & AI/ML

Agile methodology

Project management

Stakeholder communication

Education

Bachelor’s degree or equivalent

Tools

Automation tools

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 11 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

What You’ll Do

The Advanced Program Manager is responsible for driving the bank’s intelligent automation initiatives from vision through to delivery. In this role, you will own the end-to-end roadmap, guide the team, and work closely with stakeholders to identify and prioritize opportunities that deliver real business value. With a strong grasp of banking processes, agile delivery, and automation technologies including RPA and AI, you will ensure solutions are delivered to a high standard, remain compliant with regulatory requirements, and generate measurable outcomes for the organization.

This is the ideal opportunity for an automation professional who can operate confidently at both a strategic and delivery level, and who is passionate about using intelligent automation to drive meaningful change across the bank.

This is a full time position based at our office in Rosemont, IL, working a hybrid work schedule.

• Develop proactive relationships with supported business units that are built on trust, transparent communication, and a spirit of collaboration
• Assist with RPA initiative intake, initiation and planning processes
• Define epics, user stories, and acceptance criteria for automation solutions; challenge scope creep, protect the team from unplanned work, and ensure that backlog prioritization decisions are clearly communicated to the team
• Own and maintain the roadmap, prioritizing initiatives across RPA, AI/ML, and intelligent document processing (IDP) in alignment with the bank’s strategic goals
• Communicate progress, manage expectations, and build strong relationships that foster a culture of continuous improvement and automation-first thinking across the organization
• Collaborate with the Scrum Master to ensure the roadmap translates into delivery cycles that are realistic, well-sequenced, and consistently executed.
• Serve as a bridge between the RPA team, business sponsors, and technology teams; translating delivery-level blockers into business-level language and ensuring leadership understands the team’s needs as well as its outputs.
• Resolve impediments and ensure use of collaborative processes
• Support the business and provide education where needed
• Track project processes and deliverables, preparing and presenting status reports
• Use agile methodology values, principles, and practices to plan, manage and deliver solutions
• Contribute to the Center of Excellence (CoE), helping to define standards and best practices, mentor business analysis & scrum masters
• Work with Enterprise Business Process Improvement to identify process improvement automated solutions
• Look for opportunities to enhance best practices, recommending changes and improvements
• Optimizing standards, templates, and processes for the team
• Develop and maintain a good rapport with all business partners and IT

Project Support

• Assist with RPA initiative intake, initiation and planning processes
• Define epics, user stories, and acceptance criteria for automation solutions; challenge scope creep, protect the team from unplanned work, and ensure that backlog prioritization decisions are clearly communicated to the team
• Own and maintain the roadmap, prioritizing initiatives across RPA, AI/ML, and intelligent document processing (IDP) in alignment with the bank’s strategic goals
• Communicate progress, manage expectations, and build strong relationships that foster a culture of continuous improvement and automation-first thinking across the organization
• Collaborate with the Scrum Master to ensure the roadmap translates into delivery cycles that are realistic, well-sequenced, and consistently executed.
• Serve as a bridge between the RPA team, business sponsors, and technology teams; translating delivery-level blockers into business-level language and ensuring leadership understands the team’s needs as well as its outputs.
• Resolve impediments and ensure use of collaborative processes
• Support the business and provide education where needed
• Track project processes and deliverables, preparing and presenting status reports
• Use agile methodology values, principles, and practices to plan, manage and deliver solutions

Continuous Improvement

• Contribute to the Center of Excellence (CoE), helping to define standards and best practices, mentor business analysis & scrum masters
• Work with Enterprise Business Process Improvement to identify process improvement automated solutions
• Look for opportunities to enhance best practices, recommending changes and improvements
• Optimizing standards, templates, and processes for the team
• Develop and maintain a good rapport with all business partners and IT

Qualifications

• Familiarity with intelligent automation tools (e.g. RPA, AI/ML)
• 3-5 years in financial services
• Working knowledge of agile methodology, techniques, and frameworks to deliver solutions
• 3-5 years of progressive experience in related fields (e.g. project management, business analyst, etc.)
• Bachelor’s degree or equivalent.
• Excellent people and project management skills
• Ethical behavior and business practices
• Basic effective data visualization and storytelling
• Basic Communication: Speak, listen and write in a clear, thorough and timely manner
• Basic interpersonal, organizational, attention to detail and follow-up skills
• Basic identification and communication of issues early. Brings recommendations and options to resolve issues
• Ability to foster teamwork: Work cooperatively and effectively with others to set goals, resolve problems and make decisions
• Leadership skills: Works independently and self-motivated
• Make decisions: Assess situations to deliver results
• Organizational skills: Prioritizes and plans own work
• Problem-solving skills: Basic problem solving
• Change orientation: Adapts to change effectively
• Demonstrates leading by example and instills a calm, organized approach in all situations

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 $85,000.00 - $110,000.00, 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.