Jobs › Wintrust

SVP, Chief Fiduciary Officer

Wintrust · Chicago, IL · $141,000–$190,000 a year · Full time

Posted Aug 17, 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

The posting names the Prudent Investor Rule, the Uniform Trust Code and the Employee Retirement Income Security Act. Tell me about a matter where the governing law changed your recommendation.

What they are checking: Applied legal knowledge rather than a recited list.

You advise executive leadership on the fiduciary implications of new products and markets. Tell me about a time you told leadership that a growth plan carried fiduciary risk they had not priced in.

What they are checking: Willingness to slow the business at senior level.

This sits on the Wintrust Wealth Management leadership team, working with the chief executive, the senior compliance officer and the managing directors of administration. What would you want to know about how that group makes decisions before taking the role?

What they are checking: That they evaluate the leadership dynamic, which determines whether the job is doable.

What would you do

This role reviews governing documents for fiduciary risk as part of pre-acceptance. What makes you decline an account that the business wants to take?

What they are checking: Willingness to turn away revenue, which is the core of the fiduciary function.

You would be the final escalation point before the trust discretionary committee for complex discretionary decisions. How do you decide when a matter needs the committee rather than your own call?

What they are checking: Where they set their own authority boundary at the top of the function.

How do you build a fiduciary risk framework with account reviews and exception tracking that the trust officers actually work with rather than around?

What they are checking: Designing controls for adoption in a relationship business.

How do you keep fiduciary standards consistent across trusts, estates, guardianships and agency relationships when each team has its own habits?

What they are checking: Consistency across account types, which the posting names explicitly.

About the work

Walk me through how you would read a trust agreement with an ambiguous distribution standard and form an opinion for the trust officer.

What they are checking: Document interpretation depth, the daily technical work of this seat.

You would participate in regulatory exam readiness and responses with the Office of the Comptroller of the Currency and state banking regulators. What does a well-run exam preparation look like?

What they are checking: Exam experience, which is not something you can fake at this level.

The posting asks you to drive modernization of fiduciary processes, including technology and data governance. Where does technology actually help in trust administration, and where is it oversold?

What they are checking: Realism about automating judgment-heavy work.

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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 10 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 a culture that encourages an entrepreneurial spirit • We offer multiple opportunities for development and upward mobility Job Description Summary The Chief Fiduciary Officer (CFO–Fiduciary) is the senior-level Officer responsible for the design, governance, and execution of all fiduciary activities across the trust company. This role ensures that the organization consistently fulfills its fiduciary duties in accordance with applicable law, regulatory expectations, and the highest standards of prudence, loyalty, and care. As a member of the WPT leadership team, the CFO–Fiduciary partners closely with the CEO, Sr. Compliance Officer, WPT Investment Officers, Managing Directors – Administration Team Leads, Operations and Middle Office Services Team Leads, and other business line leaders to align fiduciary oversight with strategic growth while safeguarding the firm’s reputation and mitigating risk. The CFO will also manage and administer a book of business and support new business development as needed. Job Description Fiduciary Governance & Oversight • Review governing documents to provide a thorough fiduciary risk assessment, as part of the pre-acceptance process, in order for WPT Team Leads/Senior Management to assess acceptance of new business by WPT as Trustee and/or Co-Trustee • Review trust agreements for opinion on interpretation issues and/or conflict; advise trust officers and team leads with conclusions on a timely basis; present to Discretionary Committee, Trust Administration and Management Committee • Ensure consistent application of fiduciary standards across all accounts, including trusts, estates, guardianships, and agency relationships • Serve as final escalation (prior to TDC, if necessary) point for complex fiduciary matters and discretionary decisions Risk Management & Compliance • Partner with Legal, Compliance, and Risk to ensure adherence to fiduciary laws (e.g., Prudent Investor Rule, Uniform Trust Code, ERISA where applicable) • Oversee fiduciary risk management framework, including account reviews, exception tracking, and mitigation strategies • Participate in regulatory exam readiness and responses (e.g., OCC, state banking regulators, internal audit) • Monitor and mitigate litigation, reputational, and operational risks associated with fiduciary activities – in conjunction with WPT Compliance team Policy Development & Best Practices • Develop, implement, and maintain fiduciary policies, procedures, and best practices across the enterprise • Ensure scalability and consistency as the firm grows in complexity and geography • Drive modernization of fiduciary processes, including integration of technology and data governance Strategic Leadership • Act as a strategic advisor to executive leadership on fiduciary implications of new products, services, and markets • Support business development efforts by providing fiduciary expertise in high-net-worth and ultra-high-net-worth client situations • Partner with investment leadership to ensure alignment between fiduciary duty and portfolio management practices • Project Management - Identify and lead initiatives to improve consistency in account coding, processing, documentation, and reporting; Collaborate with technology colleagues to develop and enhance administrative and reporting systems that drive efficiency Talent Development & Culture • Build and lead a high-performing fiduciary organization, including senior trust officers and specialists • Lead and manage the Trust Real Estate Team • Establish training programs to elevate fiduciary acumen across the firm • Promote a culture of fiduciary excellence, accountability, and client-first decision making • Raises the profile of Wintrust Wealth Management / WPT through community involvement • Mentorship within WPT and participate outside of WPT within Wintrust in a mentorship program Qualifications • 10+ years of relevant experience • Specialized Advanced degree (PhD, J.D.) • CTFA and/or CFP Preferred or equivalent years of experience Compensation The estimated salary range for this role is $141,000- $190,000, along with eligibility to earn an annual bonus and incentive compensation. 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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