Jobs › Wintrust

Senior Employee Relations Specialist

Wintrust · Rosemont, IL · $85,000–$110,000 a year · Full time

Posted Sep 17, 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

Tell me about your employee relations experience.

What they are checking: The posting requires five to seven years in employee relations.

How do you run an engagement survey so it actually leads to change?

What they are checking: The posting names managing annual surveys, action planning, pulse surveys and focus groups.

The role is based in Rosemont with some travel. How does that fit your life?

What they are checking: The posting states the location and that some travel is required.

What would you do

How do you stay fair when a complaint is against someone senior?

What they are checking: The posting names applying corporate policies with fairness and consistency.

How do you advise a supervisor who is handling their team badly?

What they are checking: The posting names advising supervisors on treatment of staff and administration of policy.

Tell me about advising on a job elimination or an involuntary termination.

What they are checking: The posting names oversight of job restructures, eliminations and involuntary terminations.

How do you explain the reason behind a policy people dislike?

What they are checking: The posting names communicating the rationale behind policies, practices and procedures.

About the work

Walk me through how you run a workplace investigation.

What they are checking: The posting names leading investigations and documenting and communicating findings.

How do you write up findings so they hold up later?

What they are checking: Investigation documents get read by lawyers, not just managers.

How do you use case and engagement data to spot a pattern?

What they are checking: The posting names analyzing trends in engagement, retention, performance, ER cases and EEOC claims.

Practice this interview out loud.

Offer builds a real interview for this exact role at Wintrust from your resume and this job description, asks the questions one at a time, and tells you what landed. The first one is free.

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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! Rated a Top Workplace by the Chicago Tribune (past 10 years) and Employee Recommended award by the Globe & Mail (past 6 years) • Competitive pay and discretionary 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 • Family-friendly work hours • We offer opportunities to grow and develop in your career • Promote from within culture Why join this team? • We have a culture that encourages an entrepreneurial spirit • We offer multiple opportunities for development and upward mobility What You’ll Do: The Senior Employee Relations Specialist acts as a liaison between employer and employee (supporting Bank entities) , overseeing employee relations. This involves receiving and effectively handling employee complaints, escalating these complaints to the level of disciplinary or legal action when necessary, updating employees with any changes in company policy, advising supervisors on treatment of staff and company policies, responds to employee violations of policy and generally helps to resolve conflict in the workplace. Compliance and Security: • Ensure legal compliance and mitigate risk related to employment by investigating employee complaints, interpreting and applying corporate policies with fairness and consistency and, ensuring compliance with local, state and federal employment laws and regulations. Results & Accountability: • Participates in escalated ER issues, including but not limited to: leading investigations, documenting and communicating findings/resolutions, and appropriate coaching or disciplinary actions. • Analyzes data to determine trends of current talent related to engagement, retention, performance themes, ER cases, EEOC claims, BSA investigations and the like. Change Agility/Flexibility: • Analyzes both successes and failure for improvement opportunities • Provides advice and oversight of job restructures, job eliminations and involuntary terminations • Manages Engagement activities such as annual surveys, action planning, pulse surveys, and focus groups. • Partners with COE Interpersonal Skills / Social Competence: • Advises partners on employee relations framework and ensure consistent application of company policies and procedures. Stakeholder Management: • Communicates the rationale behind policies, practices and procedures • Advises supervisors on treatment of staff and appropriate administration of company policies, practices and procedures Qualifications: • 5-7 years’ experience in Employee Relations experience (experience in financial services industry a plus) • Corporate Human Relations experience • Advance computer skills • Bachelor’s degree or equivalent • Some Travel 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 annual salary range for this role is $85,000 to $110,000 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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