JobsAssociated Bank

Senior Wealth Planner

Associated Bank · Chicago 525 Monroe, IL

Posted Aug 27, 2026 · We last checked this listing on Sep 20, 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.

Behavioral

Walk me through a wealth planning strategy you built for a high-net-worth client that involved estate, tax, and business succession pieces all at once.

whether the candidate can actually integrate multiple planning disciplines rather than just naming them

Tell me about a time you had to coordinate a plan with a client's outside attorney or accountant who disagreed with your recommendation.

how the candidate handles friction with outside professional advisors while keeping the client relationship intact

Tell me about a time a planning recommendation you presented didn't land the way you expected. What did you do next?

resilience and adaptability in the room with a client, not just technical correctness

Describe a situation where you identified a cross-sell opportunity, like moving a planning client into trust or insurance services, and how you made that happen.

actual track record of driving revenue growth across product lines, since this role is partly a sales role

Tell me about a thought leadership presentation or educational event you've delivered. How did you decide what to cover and how did it go?

comfort and skill operating as a visible subject matter expert in front of clients and prospects

Tell me about a time you had to explain a complex planning concept, like a grantor trust or a buy-sell agreement, to a client who had no financial background.

communication skill and whether they can translate complexity into plain language for clients

Technical

What's the difference between how you'd structure wealth transfer planning for a client with a $5 million estate versus one with a $50 million estate?

depth of technical knowledge across the range of client complexity this role will actually see

How do you think about executive compensation planning differently for a client with heavy stock options versus one with deferred comp arrangements?

whether the candidate's technical range matches what the job description explicitly lists

What's your process for staying current on tax law changes that affect estate and wealth transfer planning, and can you give an example of a recent change you had to explain to clients?

whether the candidate treats technical currency as an ongoing discipline rather than a one-time credential

Situational

A wealth advisor brings you a business owner client who wants to sell the company in eighteen months and minimize the tax hit. How do you approach the first meeting?

structured thinking under a real time-boxed planning scenario, not just technical knowledge

A wealth advisor's client wants an aggressive insurance strategy that you think is a poor fit for their goals. How do you handle that conversation with both the advisor and the client?

ability to push back diplomatically on internal partners without damaging the relationship

How do you manage a pipeline of prospects and existing clients so nothing falls through the cracks, especially when you're supporting multiple wealth advisors at once?

organizational discipline and follow-through given the multi-advisor, multi-client structure of the role

Practice this interview out loud.

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The full job description

As published by Associated Bank.

At Associated Bank we strive to create an inclusive culture where different perspectives are valued and recognized as strengths critical to our success. If you thrive in an environment where your growth and development are encouraged and supported, then Associated Bank may be the right place for you. Associated Bank requires you to directly represent yourself and your own experiences during the recruiting and hiring process. Associated Bank conducts a thorough background check on all new hires. Associated Bank is seeking a Senior Wealth Planner to help high-net-worth individuals, business owners, and executives achieve their long-term financial goals. In this role, you'll partner with wealth advisors and business partners across the bank to develop sophisticated planning strategies that deepen client relationships and drive new business growth. This is an excellent opportunity to serve as a trusted advisor and subject matter expert while making a meaningful impact across the organization. Key Accountabilities • Partner with wealth advisors and bankers to identify and pursue new business opportunities with high-net-worth clients and prospects. • Develop customized wealth planning strategies, including estate, business succession, executive compensation, insurance, and wealth transfer planning. • Present planning recommendations and financial solutions that help clients achieve their long-term goals. • Collaborate with attorneys, accountants, and other professional advisors to coordinate comprehensive client solutions. • Drive relationship growth by identifying cross-sell opportunities across investment management, banking, insurance, and trust services. • Serve as a subject matter expert on complex financial planning concepts, tax considerations, and wealth strategies. • Deliver educational presentations and thought leadership events to clients, prospects, and internal teams. • Maintain strong prospect and client pipelines through proactive follow-up and relationship management. Education & Experience Required • Bachelor's degree in Business, Finance, or a related field, or equivalent combination of education and experience. • 4+ years of experience in wealth planning, financial planning, wealth management, or a related advisory role. • Strong knowledge of advanced financial planning concepts, investment solutions, insurance strategies, and tax planning considerations. • CFP® (Certified Financial Planner) or CWS® (Certified Wealth Strategist) designation by start date. • Strong relationship-building, presentation, and consultative sales skills. Preferred • Life, Accident & Health Insurance License. • Series 7 securities license. • CPA designation. • Experience working with high-net-worth individuals, business owners, and executive-level clients. • Experience using financial planning software and developing complex planning recommendations. We welcome and encourage applications from all qualified parties, including but not limited to people returning to the workforce, people with disabilities, those without a college degree, and veterans or those with military experience. In addition to core traditional benefits, we take pride in offering benefits for every stage of life.  • Retirement savings including both 401(k) and Pension plans.  • Paid time off to volunteer in your community.  • Opportunities to connect with others through our diversity-focused Colleague Resource Groups.  • Competitive salaries with professional development and advancement opportunities.  • Bonus benefits including well-being programs and incentives, parental leave, an employee stock purchase plan, military benefits and much more.   • Personal banking, loan, investment and insurance benefits.  Associated Bank serves more than 120 communities throughout Wisconsin, Illinois, Minnesota, and Missouri and we consider our colleagues critical to our continued success. See why our colleagues continually vote us a best place to work in the Midwest. Join our community on  Facebook ,  LinkedIn  and  X .   Compliance Statement Associated Bank is an equal opportunity employer committed to creating a diverse workforce. We support a work environment where colleagues are respected and given the opportunity to perform to their fullest potential. We consider all qualified applicants without regard to race, religion, color, sex, national origin, age, sexual orientation, gender identity, disability or veteran status, among other factors. Fully complies with all applicable enterprise policies and procedures. Acts in compliance with all applicable laws and regulations as outlined in training materials, including but not limited to Bank Secrecy Act. Responsible for reporting suspicious activity to Financial Intelligence. Responsible to report all customer complaints as prescribed and procedure violations to management or HR. Responsible to report ethical concerns as needed to Associated Bank’s anonymous Ethics Hotline. Associated Bank provides additional assistance throughout the application, interview and hiring process. Please contact  leavesandaccommodations@associatedbank.com  if you need an accommodation at any time during the process. Associated Banc-Corp participates in the E-Verify Program. E-Verify Notice  English or Spanish . Know Your Right to Work  English  or  Spanish . Associated Bank is Pay Transparency  compliant. The pay range represents anticipated base pay for this role. Actual pay may vary based on factors including, but not limited to, work location, skills, experience, education, and qualifications for the role. For certain positions, total compensation may also include incentive, commission, or bonus opportunities not reflected in the posted base pay range. $139,370.00 - $238,920.00 per year

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