Full-Time

Regional Manager

Wealth Management, Investments

Posted on 11/1/2025

Wintrust

Wintrust

1,001-5,000 employees

Community banking and wealth management provider

Compensation Overview

$90k - $114k/yr

+ Annual bonus + Variable compensation

Highland Park, IL, USA

Hybrid

Category
Finance & Banking (11)
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Required Skills
Management
Requirements
  • Bachelor’s degree.
  • Series 24, 7, 65 (or 63 and 66) required. Series 9/10 can be substituted for Series 24.
  • Five or more years of investment experience
  • Two or more years of management experience
  • Proficient leadership and interpersonal skills
  • Effective presentation, verbal and written communication skills
  • Highly proficient in Microsoft Office suite (Excel, Word, Outlook, PowerPoint, etc.).
Responsibilities
  • Direct supervisory responsibility of Financial Advisors and Senior Administrative Associates in the Northern territory of Wintrust Investments.
  • Responsible for providing Financial Advisors timely, candid and constructive performance feedback.
  • Developing Financial Advisors to their fullest potential and provide challenging opportunities that enhance the employee’s career growth.
  • Developing the appropriate talent pool to ensure adequate bench strength and succession planning.
  • Participate in recruiting efforts in respective region and for any area of needs within Wintrust Investments.
  • Special projects assigned by Managing Director or Chief Executive Officer.
  • Represent Wintrust Investments within assigned Charter Banks of Wintrust Financial to position the benefits of working closely with the Financial Advisors in those markets.
  • Maintains a high level of knowledge about investments; functions as a product menu expert for the assigned area in order to educate staff to fully utilize all product offerings to best support the sales strategy and needs of the client.
Desired Qualifications
  • Knowledge of LPL Financial platform preferred.

Wintrust Financial coordinates a network of community and commercial banks that provide banking, wealth management, insurance premium financing, mortgage origination, and related financial services across 175+ locations in Chicagoland, NW Indiana, southern Wisconsin, and Florida. Customers access products through checking and savings accounts, loans and lines of credit, and cash management, with wealth management offering advisory services and planning, premium financing enabling payment of insurance premiums over time, and mortgage origination helping clients secure home loans. The company differentiates itself by offering a broad, locally focused set of services across a wide regional footprint, tailored to community needs through its multiple divisions. Its goal is to deliver accessible, comprehensive financial solutions to individuals and businesses while expanding its network of community banks and services.

Company Size

1,001-5,000

Company Stage

IPO

Headquarters

Rosemont, Illinois

Founded

1995

Simplify Jobs

Simplify's Take

What believers are saying

  • Macatawa merger expands Midwest footprint, enhances Michigan customer base, service offerings.
  • Integration upgrades Macatawa products on April 28, 2025, providing excess liquidity, strong deposits.
  • Receives Crain's M&A award for largest banking-finance deal, boosting shareholder value.

What critics are saying

  • Michigan integration fails, eroding deposits to Fifth Third Bank within 6-12 months.
  • Commercial real estate defaults in northern Illinois slash net interest margins in 12-18 months.
  • JPMorgan Chase captures small business lending share via superior digital tech in 18-24 months.

What makes Wintrust unique

  • Wintrust operates 16 banking charters across community, commercial, specialty finance, wealth management.
  • Merger with Macatawa Bank on August 1, 2024, adds 26 Michigan branches in Kent, Ottawa, Allegan counties.
  • Macatawa acquisition, valued at $510.3 million, marks largest West Michigan bank deal in years.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

Life Insurance

Disability Insurance

401(k) Retirement Plan

401(k) Company Match

Parental Leave

Employee Assistance Program (EAP)

Flexible Spending Account (FSA)

Employee Stock Purchase Plan

Transportation and Commuting Benefits

Pet Insurance

Company News

Yahoo Finance
Feb 25th, 2026
Regional bank stocks deliver solid Q4 results, revenues beat estimates by 1.5%

Wintrust Financial reported Q4 revenues of $715.6 million, up 11% year-on-year and exceeding analyst expectations by 1.8%. The regional bank delivered a strong quarter with beats on both revenue and net interest income estimates. CEO Timothy Crane highlighted 19% net income growth and record results across several metrics, driven by robust loan and deposit growth in the Chicago-area bank's markets. The company achieved a stable net interest margin and strong balance sheet expansion. Across the regional banking sector, the 95 tracked banks reported satisfactory Q4 results, with revenues beating consensus estimates by 1.5% on average. Share prices have remained relatively unchanged following earnings announcements. Wintrust Financial's stock has risen 3.4% since reporting and currently trades at $149.55.

Yahoo Finance
Feb 1st, 2026
Shaker Investments exits $3.47M Wintrust Financial stake despite 13% gain

Shaker Investments sold its entire 26,185-share stake in Wintrust Financial on 30 January, representing an estimated $3.47 million transaction and reducing its exposure by 1.44% of assets under management. The exit came despite Wintrust shares rising 13% over the past year, though the stock underperformed the S&P 500 by approximately two percentage points. Wintrust, a regional financial holding company offering community banking and wealth management services, primarily operates across the Midwest and select Florida markets. The sale appears to reflect portfolio repositioning rather than concerns about Wintrust's performance. Over 30% of Shaker's assets are now concentrated in industrials and mega-cap technology stocks, with top holdings including Axos Financial, Broadcom and Nvidia, suggesting a preference for companies with dominant market positions and stronger growth prospects.

Yahoo Finance
Jan 21st, 2026
Wintrust hits record $824M net income, climbs to third in Chicago deposit market share

Wintrust Financial reported record full-year 2025 results, with net income of $824 million, up from $695 million in 2024. Total assets reached approximately $71 billion. Fourth-quarter net income hit a record $223 million. The company achieved mid- to high-single-digit organic growth in loans and deposits, each rising roughly $1 billion in the fourth quarter. Net interest margin remained stable around current levels, supporting record net interest income. Wintrust advanced to third place in Chicago deposit market share whilst posting strong gains in Wisconsin and West Michigan. For 2026, management targets mid- to high-single-digit loan and deposit growth with net interest margin expected to remain relatively stable. The company retains share buyback authorisation of slightly over $200 million whilst prioritising organic growth and anticipating revenue growth to outpace expenses.

GlobeNewswire
May 9th, 2025
Wintrust Financial Corporation Announces Pricing of $425 Million Preferred Stock Offering

ROSEMONT, Ill., May 08, 2025 (GLOBE NEWSWIRE) -- Wintrust Financial Corporation (“Wintrust”) (Nasdaq: WTFC) today announced that it has priced an...

Equipment Leasing and Finance Association
Apr 8th, 2025
Key Equipment Finance refinancing for The Dutra Group

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