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Financial Advisor

Wintrust · Chicago, IL · Full time

Posted Jan 10, 2025 · 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

What does acting in a client's best interest mean to you in practice?

What they are checking: Their ethical grounding and understanding of conduct standards for advisors.

Tell me about a client relationship you grew over time. What made it work?

What they are checking: Their focus on long-term relationships rather than one-time sales.

How do you work with bankers so they feel comfortable referring their customers to you?

What they are checking: Whether they can build trust inside the bank network that feeds referrals.

What would you do

How would you build a client base in the Chicago area as a new advisor with Wintrust Wealth Management?

What they are checking: Whether they have a realistic plan to grow a book, including referrals from community bank partners.

How do you explain market risk to a client who just watched their portfolio drop?

What they are checking: Their ability to keep clients calm and focused on long-term plans.

Wintrust works with private trust and asset management companies. When would you bring in a trust specialist?

What they are checking: Whether they know when to collaborate across the wealth firm's businesses.

A client wants to put most of their money into one stock they love. What do you do?

What they are checking: How they handle concentration risk while respecting a client's wishes.

About the work

Walk me through your first meeting with a business owner who wants help planning for retirement.

What they are checking: Their discovery process, including goals, risk tolerance and the business itself.

How do you stay compliant with FINRA rules in your communication and record keeping?

What they are checking: Their knowledge of regulatory requirements that protect clients and the firm.

Which licenses do you hold, and how do you keep your knowledge current?

What they are checking: Whether they are properly licensed and committed to ongoing learning.

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 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 $62 billion in assets. Wintrust is a financial holding company with approximately $50 billion in assets under management and traded on the NASDAQ: WTFC. Built on the "HAVE IT ALL" model, Wintrust offers sophisticated technology and resources of a large bank while focusing on providing service-based community banking to each and every customer. Wintrust operates fifteen community bank subsidiaries with over 170 banking locations in the greater Chicago and southern Wisconsin market areas. Additionally, Wintrust operates various non-bank business units, including commercial and life insurance premium financing, short-term accounts receivable financing, out-sourced administrative services, mortgage origination and purchase, wealth management services, and qualified intermediary services for tax-deferred exchanges. Why join us? • An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 8 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 • Family-friendly work hours • Promote from within culture Why join this team? • We offer advisors the best of both worlds—the technology, products, benefits, and business development opportunities of a large corporation as well as the supportive culture, reputation for personal service, and lasting client relationships of a boutique firm • We hold ourselves to the highest standards of service and integrity in the industry • W e have a strong reputation for quality service and impeccable ethics What You'll Do • Build rapport and professional relationships with clients, prospects, and colleagues • Be committed to client retention, client recruiting, and superior customer service • Gather assets for fee-based and traditional brokerage accounts • Go on calls with clients and potential clients • Maintain a high level of compliance with FINRA, SEC, and firm rules and regulations • M eet sales quotas • A ssess client's overall financial picture, truly understand their needs and then develop a relevant, solid financial plan • Oversee the course of financial plans and updating it if necessary, to ensure profits • Cultivate our client base and build win-win relationships • Adhere to compliance with all industry rules and regulations • Administer presentations for new prospects and referrals • Work collaboratively with other team members • Identify and deepen relationships with clients and potential clients • Possess knowledge of a wide array of financial products and services • Keep up on new industry trends and research the market to back up financial consulting decisions • N etwork, generate leads and seize opportunities to sell mutual funds, stocks, bonds, etc • Other duties, as they arise Qualifications • Series 7, 66 or 63 and 65 • Proven work history with experience as a financial advisor, planner, specialist or another relevant role • Consistent track record of successful financial guidance • Ability to analyze the market data in order to formulate and provide appropriate, data-based financial advice • Solid communication, negotiation, and presentation skills • Attention to detail and consistent accuracy with all data • Highly articulate and able to explain complex information clearly and simply s • Self-motivated • Strong working knowledge across a variety of financial products and services (debt management, cash management, insurance coverage, investments, etc.) 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 This position is commission-based, with earning directly tied to individual production. 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 be Chicago’s Bank® and Wisconsin's Bank®, we need to reflect that diversity both in all the communities we serve, the people we employ, the organizations we work with, and our banking and lending practices. 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, national origin, sex, sexual orientation, gender identity and expressions, genetic information, marital status, age, disability, or status as a covered veteran or any other characteristic protected by law.

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