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This position has closed. Wintrust removed this listing from their careers page on Sep 30, 2026. The interview prep below is still useful, and there are similar open roles at the bottom of this page.

Financial Assistant

Wintrust · Frankfort, IL · $20.20–$24.04 an hour · Full time

Posted Sep 2, 2026 · We last checked this listing on Sep 29, 2026

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

This role supports a financial advisor team in the Frankfort office with administrative, sales and client service work. What advisor support have you done?

What they are checking: Direct experience in the supporting seat

You'd handle newsletters, birthday cards and other client communications. Why do those small touches matter in wealth management?

What they are checking: Whether they see the point of the routine work

What would you do

You'd prepare advisors for client review meetings including presentations and updated profiles. What makes an advisor well prepared for a review?

What they are checking: The value this seat actually adds

You'd keep compliance files clean and current and ensure processes are followed. What happens if a compliance file is not right?

What they are checking: Consequence awareness in a regulated practice

You'd act as the team's office manager as well. How do you balance that against client work when both need you?

What they are checking: The dual role the posting names

A client calls upset and the advisor is out. What do you do?

What they are checking: Handling a client alone within your limits

The posting asks for three or more years in financial services and customer service, at $20.20 to $24.04 an hour plus bonus, in Frankfort. Does that work for you?

What they are checking: The stated experience and pay, raised plainly

About the work

You'd facilitate new client onboarding, opening and maintaining accounts and managing paperwork. Walk me through onboarding a new client cleanly.

What they are checking: The named process, as a sequence

You'd manage banker referral flow in the firm's relationship system. How do you make sure a referral does not go cold?

What they are checking: The named system and a real process behind it

The posting prefers securities and insurance licences but does not require them to start. Which do you hold, and would you pursue the rest?

What they are checking: The stated licensing preference, confirmed with intent

Practice this interview out loud.

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The full job description

As published by Wintrust.

Wintrust Wealth Management serves the financial needs of private clients, including high net worth individuals, business owners, and institutions. Since our founding in 1931, we have been helping clients meet their increasingly complex financial goals with the highest standards of service and integrity. Through our four companies, Wintrust Investments LLC, Wintrust Private Trust., Great Lakes Advisors LLC, and The Chicago Deferred Exchange Company LLC, we offer comprehensive wealth management solutions, including investment, trust, and asset management services. Wintrust Wealth Management is a division of Wintrust, a financial services company with more than $66 billion in assets. 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 benefits 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 employ approximately 300 associates and are responsible for more than $25+ billion of client assets • Strong track record of valuing and investing in existing talent by providing opportunities for growth and advancement • We hold ourselves to the highest standard of service and integrity in the industry • We have a strong reputation for quality service and impeccable ethics What you will do • As a Wintrust Wealth Management Financial Assistant, you will support our Financial Advisor Team located in our Frankfort, IL office. • Help in delivering client investment solutions by providing a full complement of administrative support, sales support, customer service, and other related resources to your financial advisors and clients • Facilitate new client onboarding process - open and maintain client accounts, manage account paperwork, track and record client correspondence, generate various performance and activity reports, along with other operational activities. • Schedule and manage client reviews. Prep Financial Advisor for client review meetings, including preparing presentations and updating client profiles. Enter and maintain CRM notes as directed. • Ensure the team is compliant in following all processes and procedures; maintain clean and up-to-date compliance files. • Act as the team’s Office Manager. Order supplies, keep marketing materials up to date, and keep the office running smoothly. • Work to deepen and enhance inter-company relationships. Manage banker referral flow activity for team in Salesforce system. • Cultivate a service environment targeted towards enhancing the client experience • Handle various client communications and mailings, including monthly newsletters, birthday cards, Christmas cards, etc. Qualifications • 3+ years of relevant experience in the financial industry and customer service experience strongly preferred • Working knowledge of Microsoft Word, Excel, and Outlook; knowledge of Salesforce and Workday desirable. • FINRA Series 7 and 66 licenses and Illinois Insurance License preferred, but not required to start • Relationship management skills • A thorough understanding of a client service environment 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 hourly rate for this role is $20.20 - $24.04, along with eligibility to earn an annual bonus. Actual pay rate 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.