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Treasury Management Sales Associate

Wintrust · Chicago, IL · Full time

Posted Aug 21, 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 supporting someone else's deal. How did you add value without taking it over?

What they are checking: The supporting posture this role requires alongside sales representatives.

You would get exposure to executive management. How do you prepare for a meeting where a senior leader may ask you something directly?

What they are checking: Readiness in a role the posting says has unusual visibility.

Wintrust also posted a Treasury Management Implementation Specialist and a Treasury Management Support Specialist, both in Rosemont and both hourly. This one is in Chicago supporting sales. Why this seat?

What they are checking: Self-placement across the three treasury roles posted together.

This supports sales across several Wintrust chartered banks from Chicago. What do you want to know about the size of the portfolio and how the sales representatives are covered?

What they are checking: Checking the real workload and coverage model before accepting.

What would you do

A sales representative wants a proposal by tomorrow morning and the data is not complete. What do you give them?

What they are checking: Supporting a salesperson under time pressure without guessing.

Describe a portfolio-wide analysis you would run if you had a free week. What would you look for?

What they are checking: Initiative on the special projects this posting describes.

A client is affected by a product change. How do you plan the notification so it does not damage the relationship?

What they are checking: Change communication, which this posting lists as project work.

About the work

This role supports middle market treasury sales. Walk me through analyzing a prospect's current bank services and building a proposal from it.

What they are checking: The competitive analysis and product design this posting puts first.

How do you spot from usage patterns that a client is paying for something they do not need, or missing something they do?

What they are checking: Reading a relationship review the way this role is expected to.

How do you manage the workflow of a deal through case creation, agreements and implementation?

What they are checking: Ownership of the deal's administrative path, which this posting names.

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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 • Family-friendly work hours • With 175+ community bank locations, we offer opportunities to grow and develop in your career • Promote from within culture Why join this team? • We have an energetic, team-oriented environment; • Growing team in a growing company that provides opportunities for individual growth and advancement; • Our team is in a unique position that allows us to collaborate with other departments, have exposure to executive management, and implement new products and services; Job Description Summary: The Sales Associate supports our Middle Market Treasury Management Sales team throughout various Wintrust chartered banks. The Sales Associate works alongside Sales Reps, Implementation Reps, Customer Service Professionals, Product Managers and Relationship Managers assisting with a high volume of tasks related to pre- and post-sales analysis, client reviews, presentations and research. The Sales Associate will play an active role in helping to manage the sales and implementation process for new and existing clients. The Sales Associate must be versatile and well organized. There is a strong need for flexibility to adapt to a growing and demanding client portfolio, product enhancements and special projects. The Sales Associate should have an outgoing personality with desire for salesmanship emphasizing the value of our products to the client’s operation and business needs. What You’ll Do: • Time Spent on Customer and Prospect Presentations/Calling: Analyze existing services at competing bank and usage patterns. Design product group to meet current needs. Create individual cost analysis pricing. Recommend additional treasury products and services as well as account structures based on efficiency, cost, fraud protection, automation and ease of use. Create customized presentation for each prospect based on overall analysis. Pre call preparation with TM Sales Rep includes research on the company, overall relationship and providing product recommendations. Joint calling with the Sales Rep and/or Relationship Manager. • Time Spent on Relationship Reviews: Review existing commercial banking relationships on a self-designated periodic basis or instructed by Sales. Analyze existing usage patterns and use this data to identify and recommend additional Treasury products and services as well as create account structures based on efficiency, cost, fraud protection, automation and ease of use. • Time Spent on Portfolio Maintenance & Implementation: Assist with case creation, collection of agreements and managing the workflow of a deal. Act as another resource for complex client service issues including discovery, research escalation and resolution. • Time Spent on Special Projects: This may include portfolio wide product usage analysis; identifying, notifying and implementing product upgrades; researching customers affected by a product or service change; analyzing the impact of a regulatory change. • Time Spent on Sales Pipeline Management: Maintain accurate portfolio planning and tracking for revenue forecasting and goal measurement. Knowledge/Skills/Background/Experience: • 2-5 years Banking/Treasury Management experience • High school degree or equivalency - B achelor's degree preferred • Customer facing/sales experience; Sales oriented and desire to be in customer-facing role • Advanced Computer Skills, MS Excel and PowerPoint and ability to gain and apply knowledge of information systems • Experience in commercial banking with Treasury Management product knowledge • Ability to work independently, while establishing strong working relationships with other areas of the Bank • Ability to handle sensitive customer information and issues with tact and discretion • Job requires driving to various Wintrust Charters, Rosemont HQ, customers and prospect calls across the markets you cover in the Chicago area 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 $50,000 - $7 0 ,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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