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Associate Product Owner - Enterprise Salesforce

Wintrust · Rosemont, IL · $71,000–$92,000 a year · Full time

Posted Sep 10, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

The role sometimes needs nights or weekends for releases, in Rosemont. How does that fit your life?

What they are checking: The posting states it plainly, so it is asked plainly.

How do you keep up with what a platform like Salesforce can do as it changes?

What they are checking: The posting names staying current and identifying opportunities in new functionality.

What would you do

How do you draw requirements out of a business stakeholder who describes a solution rather than a problem?

What they are checking: The posting names eliciting and assessing functional requirements, which is where this role earns its keep.

You find a defect late and the release date is fixed. What do you do?

What they are checking: The moment the role either protects users or does not.

How do you decide what goes on the roadmap when everyone's request is urgent?

What they are checking: The posting names prioritizing and aligning business requests to the strategic roadmap.

How would you train end users on something that changes how they work?

What they are checking: The posting names defining training content and participating in sessions as the product expert.

About the work

Tell me about your Salesforce experience and what you have configured or owned.

What they are checking: The posting prefers a year or more on the platform, so it is checked plainly.

Walk me through writing a user story that a developer could build from.

What they are checking: The posting names business requirements in the form of JIRA user stories.

Walk me through running user acceptance testing on a release.

What they are checking: The posting names executing UAT and reporting defects before implementation.

How do you build a process flow or business architecture diagram that people actually use?

What they are checking: The posting names current and target state process flows as a deliverable.

Practice this interview out loud.

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The full job description

As published by Wintrust.

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? • We are a high performing, collaborative, and diverse team focused on transforming the business through engaging work on enterprise-wide product innovation • You will join a major product implementation that will define the target servicing experience on a best-in-class Case Management / CRM platform for the Enterprise • Opportunity to work and grow with experienced Product Owners and Managers • Work across disciplines and departments, with opportunities for exposure to and partnership with Executive and Senior Management in leading strategic initiatives Position Overview The Associate Product Owner Salesforce will play a key role in evolving the Enterprise Salesforce platform as aligned to the Enterprise/Niche CRM Strategy. What You’ll Do • Product Design and Innovation: Liaise with Business Stakeholders and End Users, Enterprise Salesforce Product Team (and other Product Teams as relevant), Enterprise Salesforce IT Team, and additional IT partners across Wintrust to elicit and assess functional requirements and consult on platform capability enhancement and expansion. • Product Requirements Definition: Produce related project documentation to support platform capability enhancement and expansion including: business requirements in the form of JIRA user stories with related current and target state process flows / business architecture diagrams, as well as supporting user acceptance test scripts to drive business validation. • Product Testing and Validation: Execute User Acceptance Testing and report defects back to IT to resolve issues prior to implementation. • Product Roll-out and Training: Partner with Salesforce Product Team members and Learning & Development Partners to define custom training content, participating in end-user training sessions as the Product SME. • Product Management and Administration: Assist end users with business administration, enhancements, production issues and related projects; work with Salesforce Product Team members to prioritize and align business requests to the Strategic Roadmap, and escalations as required for production hot fix. • Maintain product documentation, process flows, business rules, and Salesforce-related requirements. • Stay current on Salesforce platform capabilities and best practices and identify opportunities to leverage new functionality. Qualifications • 2-3 years of related experience • Bachelor’s Degree is preferred • Willingness to work occasional nights and weekends in support of product releases • 1+ years working in a financial services environment with special emphasis on coordinating business, functional requirements and/or project management across cross-functional teams, programs, or projects; working in agile software delivery; working with JIRA or similar agile tool. • 1+ years of experience with the Salesforce CRM Platform and/or related technical acumen preferred • Salesforce Administrator Certification a plus and/or Certified Scrum Product Owner (CSPO) Certification are a plus. 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 $71,000-$92,000, 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. #LI-ONSITE 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.

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