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WTI Sales Support Team Lead

Wintrust Financial Corporation
Chicago, IL Full Time
POSTED ON 1/7/2026 CLOSED ON 2/7/2026

What are the responsibilities and job description for the WTI Sales Support Team Lead position at Wintrust Financial Corporation?

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 11 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 200 community bank locations, we offer opportunities to grow and develop in your career
  • Promote from within culture

Wintrust Investments Sales Support Team Lead

Within our fast-paced growth environment, this position is key in ensuring that the Financial Associates receive the proper support, coaching, and career development. The successful candidate will be ethical, disciplined, accountable, highly organized, have excellent communication skills, to include critical listening, and be an adept problem-solver.

The Role Involves a Range Of Responsibilities, Including

  • People Coaching: Working one-on-one and in groups, providing employees with coaching, assist in tracking annual goals, and providing performance feedback.
  • Reporting: Both on a periodic and ad hoc basis, preparing high-quality and insightful sales reports, presentations, dashboards.
  • Project Management: Assisting Director of Sales Support with specific projects or initiatives aimed at improving overall sales performance, the effectiveness of the Financial Associates, and the client experience.
  • Coordination: Organizing sales meetings and events. Administer the HR system Workday for direct reports.
  • Transition Management: Assist the Director of Sales Support and the Director of Recruiting in preparing for Financial Advisor transitions and support the new Financial Advisor post conversion.
  • Sales Management Teamwork: Maintaining strong relationships with the Sales Management team as well as senior leadership.

Requirements

  • A bachelor’s degree in business administration, finance, marketing, or a related field preferred.
  • Previous experience in a sales support role or administrative position is advantageous.
  • Previous experience in an investment-related field, finance, or banking is preferred.
  • Highly proficient in Microsoft Suite to include Excel (and CSV files), Outlook, PowerPoint, and SharePoint; Power BI; Salesforce.
  • Effective presentation, verbal, and written communication skills.
  • Strong organizational skills, and the ability to multitask and prioritize effectively are essential.
  • Series 7, 65 (or 63 and 66) required. Series 24 or 9/10 preferred.

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

Wintrust Financial Corporation (including community banking and financial services subsidiaries) is an Equal Opportunity/Affirmative Action/Veterans/Disability employer.

Compensation

The estimated salary range for this role is $50,000 - $65,000, 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.

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.

Salary : $50,000 - $65,000

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