CEO & President - Chicago Deferred Exchange Company

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 Executive Officer (CEO) is responsible for leading the overall direction and success of Chicago Deferred Exchange Company. This role provides strategic leadership, financial performance, and regulatory oversight. The CEO works closely with employees, clients, and industry partners to ensure exceptional service, protect client exchange funds, and maintain CDEC’s reputation as a trusted leader in the 1031 exchange industry. This individual will drive innovation, strengthen key relationships, and position the organization for continued success.

Essential Responsibilities

• Develop and execute the strategic vision, business objectives, and long-term growth strategy for CDEC.
• Provide leadership and oversight for all operational, financial, and administrative functions of the organization.
• Identify new business opportunities, expand market presence and drive revenue growth.
• Stay informed on legislative, regulatory, and industry developments affecting 1031 exchanges and recommend proactive business strategies.
• Establish and maintain operational policies, procedures, and internal controls that mitigate risk and maintain regulatory compliance.
• Oversee financial planning, budgeting, forecasting, and profitability.
• Lead, develop, and mentor executive leadership and staff while fostering a culture of collaboration, accountability, and constant improvement.
• Promote innovation and technology solutions that increase operational efficiency and client experience.

Qualifications

• Bachelor’s degree in business administration, Finance, Accounting, Real Estate, Law, or a related field required.
• MBA, JD, CPA, or other advanced professional designations are preferred.
• 10-15 years of progressive leadership experience in financial services, 1031 exchange administration, banking, real estate, and trust services.
• Strong executive leadership experience with responsibility for organizational strategy, operations, and financial performance.
• Familiarity with Section 1031 exchanges, Qualified Intermediary Services, fiduciary responsibilities, and regulatory compliance.
• Proven success in business development, client relationship management, and organizational leadership.
• Outstanding communication, presentation, negotiation, and interpersonal skills.
• Ability to build trust and develop strong relationships with clients, employees, and business partners.
• Strong analytical, decision-making, and problem-solving skills.

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 salary range for this role is $225,000 - $325,000, along with eligibility to earn an annual bonus. 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.

Wintrust provides community and commercial banking, specialty finance and wealth management services, delivering the sophisticated solutions of a large bank through a relationship-focused approach built from our community banking roots.

Wintrust may collect personal information from you in connection with the application process. Wintrust complies with the California Consumer Privacy Act of 2018, and its policy may be found here