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Wintrust

60 Wintrust Financial Financial Planning Manager Jobs Hiring Near You

Wintrust

SVP, Financial Modeling

Rosemont, IL · On-site

$236K/yr

Wintrust provides community and commercial banking, specialty finance and wealth management services through its 16 bank charters and nine non-bank businesses. Wintrust delivers the sophisticated ...

Wintrust

WTI Support Team Specialist

Chicago, IL · On-site

$50K - $65K/yr

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 ...

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Wintrust Jobs Information

Do workers at Wintrust get paid breaks?

No. Most people don’t get paid breaks.
68% of people say they don’t get paid breaks.
Based on data from 19 people who took the Breakroom Quiz between December 2024 and April 2026.

Does Wintrust pay people when they’re sick?

Yes. Most people get paid when they’re sick.
90% of people say they would get paid if they were sick but scheduled to work.
Based on data from 20 people who took the Breakroom Quiz between December 2024 and April 2026.

At Wintrust, are sick days and vacation days separate paid time off?

Sick days and vacation days are separate paid time off.
70% of people say they don’t have to use vacation days when they’re out sick.
Based on data from 10 people who took the Breakroom Quiz between June 2025 and April 2026.

Is the health insurance from Wintrust affordable enough for their workers?

Most people say the health insurance costs are okay.
88% of people say the health insurance costs are okay
Based on data from 16 people who took the Breakroom Quiz between April 2025 and February 2026.

Do people get paid time off at Wintrust?

Most people get paid time off work.
91% of people say they get paid time off.
Based on data from 11 people who took the Breakroom Quiz between June 2025 and April 2026.

How far ahead of time do people find out their work schedule?

Only some people find out their schedule four weeks ahead of time.
  • 30% of people with changing schedules find out their shifts one week or less ahead of time.
  • 10% of people with changing schedules find out their shifts two weeks ahead of time.
  • 20% of people with changing schedules find out their shifts three weeks ahead of time.
  • 40% of people with changing schedules find out their shifts four weeks or more ahead of time.

Based on data from 10 people who took the Breakroom Quiz between December 2024 and December 2025.

Do workers at Wintrust worry about hours?

Most people don’t worry about getting enough hours.
100% of people report they don’t worry about getting enough hours.
Based on data from 14 people who took the Breakroom Quiz between December 2024 and December 2025.

Do Wintrust workers get to choose the shifts they work?

Most people get to choose which shifts they work.
69% report that they have enough control over which shifts they work.
Based on data from 13 people who took the Breakroom Quiz between December 2024 and December 2025.

How easy is it for Wintrust workers to change shifts?

Most people find it easy to change shifts.
100% of people report that it’s easy to change shifts if they need to.
Based on data from 10 people who took the Breakroom Quiz between December 2024 and December 2025.

How easy is it to get time off at Wintrust?

Most people find it easy to get time off.
100% of people report it’s easy to get time off.
Based on data from 17 people who took the Breakroom Quiz between December 2024 and April 2026.

Do Wintrust managers change schedules at the last minute?

Most managers don’t change people’s schedules at the last minute.
100% of people say their manager doesn’t change their shift schedule at the last minute.
Based on data from 14 people who took the Breakroom Quiz between January 2025 and December 2025.

Do jobs at Wintrust spill into time workers aren’t paid for?

Rarely. The job doesn't usually spill into unpaid time.
8% of people report that their job takes up time that they don’t get paid for.
Based on data from 12 people who took the Breakroom Quiz between December 2024 and December 2025.

How easy is it to take sick days at Wintrust?

Most people find it easy to take sick days.
95% of people report that it’s easy to take time off if they are sick.
Based on data from 19 people who took the Breakroom Quiz between December 2024 and April 2026.

Is working at Wintrust good if you’re a parent or caregiver?

Most parents and caregivers say this is a good place to work.
100% of people who care for a child or other relative report this is a good place to work.
Based on data from 5 people who took the Breakroom Quiz between January 2025 and February 2026.

Do people at Wintrust feel treated with respect by their managers?

Most people feel treated with respect by their managers.
95% of people say they’re treated with respect by their managers.
Based on data from 19 people who took the Breakroom Quiz between December 2024 and April 2026.

Do people at Wintrust get to take their breaks without interruption?

Most people get breaks without interruption.
89% of people report that they get to take their breaks without interruption.
Based on data from 19 people who took the Breakroom Quiz between December 2024 and April 2026.

Is it stressful to work at Wintrust?

Most people feel stressed out here.
78% of people say they often feel stressed out at work.
Based on data from 18 people who took the Breakroom Quiz between January 2025 and April 2026.

Do people at Wintrust enjoy their jobs?

Only some people enjoy their job.
47% of people report they don’t enjoy their job.
Based on data from 17 people who took the Breakroom Quiz between December 2024 and April 2026.

Do people at Wintrust recommend working with their team?

Only some people recommend working with their team.
55% of people report that they wouldn’t recommend working with their immediate team to a friend.
Based on data from 20 people who took the Breakroom Quiz between December 2024 and April 2026.

Do people get enough training when they start at Wintrust?

Some people didn’t get enough training when they started.
37% of people report they didn’t get enough training when they started working here.
Based on data from 19 people who took the Breakroom Quiz between December 2024 and April 2026.

Do people get support to advance at Wintrust?

Most people are given support to advance their career here.
In the last year, 69% of people report being given support to advance their career here.
Based on data from 16 people who took the Breakroom Quiz between December 2024 and April 2026.

Do people think Wintrust’s headquarters understands what’s happening where they work?

Some people think headquarters doesn’t understand what’s happening where they work.
65% of people think that this employer’s headquarters or owners don’t have a good understanding of what’s really happening where they work.
Based on data from 17 people who took the Breakroom Quiz between January 2025 and April 2026.

Do workers feel well informed about how Wintrust is doing?

Most people feel well informed about how the company is doing.
72% of people feel that they are kept well informed about how the company is doing as a whole.
Based on data from 18 people who took the Breakroom Quiz between December 2024 and April 2026.

What other companies are hiring for Financial Planning Manager jobs?

What are the most popular jobs at Wintrust Financial?

CEO & President - Chicago Deferred Exchange Company

Wintrust

Chicago, IL • On-site

$225K - $325K/yr

Full-time

Medical, Dental, Vision, Life, Retirement

Posted 4 days ago

Wintrust rating

8.0

Company rating: 8.0 out of 10

Based on 20 frontline employees who took The Breakroom Quiz

71st of 171 rated banks

Job description

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.

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