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Trust Associate I

Wintrust · Lake Forest, IL · $20.19–$26.44 an hour · Full time

Posted Aug 28, 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

Trust work involves families in difficult moments — a death, a dispute. How would you handle a call from a grieving beneficiary?

What they are checking: Whether they can handle grieving or distressed family members with patience and care, since trust work often happens during very difficult moments.

How do you work with a trust officer who is on the road seeing clients?

What they are checking: Whether they can support a busy trust officer who is often away, keeping work moving and communication clear without constant direction.

What would you do

How would you handle a beneficiary asking for a distribution the trust terms do not clearly allow?

What they are checking: Whether they read trust terms carefully and know when to escalate rather than decide, because acting beyond the document can create real liability.

Two family members give you conflicting instructions. What do you do?

What they are checking: Whether they handle conflicting family instructions by following the trust terms and escalating, rather than picking a side between beneficiaries.

What would you not discuss, and with whom, in a family trust?

What they are checking: Whether they understand confidentiality inside a family, since beneficiaries are often related but not entitled to the same information about the trust.

This is a first-level associate role in Lake Forest. What do you want this to lead to, and what would you want to know about the team before you took it?

What they are checking: Whether they have a real sense of where they want to grow and ask thoughtful questions about the team before committing to this role.

About the work

This is an entry trust role supporting a wealth management business serving high net worth clients and institutions, based in Lake Forest. What do you understand a trust to be and why someone sets one up?

What they are checking: Whether they understand what a trust is and why people create one, which is the basic knowledge this wealth management role builds on.

What is the difference between a trustee's duty to a beneficiary and a bank's duty to a customer?

What they are checking: Whether they understand fiduciary duty and how it differs from ordinary customer service, since that distinction shapes every decision in trust work.

You'd support administration across accounts. How do you keep records accurate on something that runs for decades?

What they are checking: Whether they keep careful records that will hold up over decades, because trusts can run for generations and errors compound over time.

Trust accounts carry tax and reporting deadlines. How would you make sure none of them slips?

What they are checking: Whether they have a reliable system for tracking tax and reporting deadlines, because a missed trust deadline can cause real financial consequences.

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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 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 firm? • 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: • Adheres to all internal and external regulatory requirements, standards, guidelines, policies and procedures and has the ability to maintain confidentiality. • Works with the Trust Officer to complete daily tasks including utilizing proper forms, processes and procedural elements that pertain to specific daily workflow, work with internal operations staff regarding account openings, closings, and asset transfers (if applicable) and basic daily tasks including opening and sorting incoming mail, process outgoing mail, and phone coverage. • Assists Trust Officer in responding to routine customer and internal account inquiries, performs necessary research requested for resolution of each matter, provides follow up, as necessary, in a timely manner. • Creates and maintains proper account electronic documentation and ensures account paper files are in good order and account coding is accurate and maintained. • Accurately executes instructions from Trust Officers including cash movement disbursements (e.g., check requests, ach or wiring funds, paying bills) and receipt of funds, establishes new accounts on the system, maintains account information, closes accounts/trade orders in a timely manner. • Performs standard account monitoring and notifies the Trust Officer when overdrafts or large balances are discovered. • Creates and organizes PowerPoint slide presentations and Excel spreadsheets, when necessary. • Performs special projects, as assigned, by the Trust Officer. • Acts as back-up for another TA, if necessary, on intermittent basis. • The responsibilities above are not exhaustive. There may be other responsibilities that will be required from time to time. Those expectations will be clearly defined at the time the request is made. Knowledge and Skills: • Bachelor’s degree preferred • 1 to 3 years in a supporting role • Excellent Microsoft Office suite skills • Basic skills in applied mathematical formulas • Skill in word processing and spreadsheets • Ability to clearly articulate issues, problems, solutions, concerns, and other information in verbal and written communications • Attention to detail and accuracy • Ability to multitask, follow instructions, and have a keen attention to detail • Basic knowledge of accounting principles • Basic knowledge of Trust terms and functions • Knowledge of basic banking functions • Excellent teamwork skills • Adheres to the highest ethical standards • Exceptional client service skills • Protects confidentiality 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 $20.19 -$26.44, 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. #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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