DEF 14A of Wintrust Financial Corp, Apr 4, 2024

DEF 14A of Wintrust Financial Corp

Filed Apr 4, 2024 · FY20230001104659-24-043637

Open on EDGAR

  1. WINTRUST FINANCIAL CORPORATION NOTICE OF ANNUAL MEETING OF SHAREHOLDERS TO BE HELD ON MAY 23, 2024

    | About the Meeting | 1 | | Board of Directors, Committees and Governance | 4 | | Director Compensation | 15 | | Security Ownership of Certain Beneficial Owners, Directors and Management | 19 | | Delinquent Section 16(a) Reports | 21 | | Related Party Transactions | 21 | | Corporate Social Responsibility | 22 | | Proposal No. 1 — Election of Directors | 26 | | Executive Officers of the Company | 33 | | Executive Compensation — Compensation Discussion & Analysis | 35 | | 2023 Summary Compensation Table | 54 | | 2023 Grants of Plan-Based Awards Table | 55 | | 2023 Outstanding Equity Awards at Fiscal Year-End Table | 56 | | 2023 Option Exercises and Stock Vested Table | 58 | | 2023 Nonqualified Deferred Compensation Table | 58 | | Potential Payments Upon Termination or Change in Control | 59 | | Compensation Committee Report | 64 | | CEO Pay Ratio Disclosure | 64 | | Pay Versus Performance | 65 | | Equity Compensation Plan Information | 69 | | Proposal No. 2 — Approval of, on an Advisory (Non-Binding) Basis, the Company’s Executive Compensation as described in this Proxy Statement | 69 | | Report of the Audit Committee | 70 | | Proposal No. 3 — Ratification of Ernst & Young LLP to Serve as the Company’s Independent Registered Public Accounting Firm for Fiscal Year 2024 | 71 | | Audit and Non-Audit Fees Paid | 71 | | Shareholder Proposals for the 2025 Annual Meeting | 72 | | Other Business | 72 |

  2. Board of Directors

    Board of Directors

  3. Committee Membership

    Committee Membership The following table summarizes the current membership of the Board and each of its committees as of the date of this Proxy Statement:

  4. Committee Membership

    | Board of Directors | Nominating and Corporate Governance Committee | Audit Committee | Compensation Committee | Risk Management Committee | Finance Committee | Information Technology/ Information Security Committee | Executive Committee | | Elizabeth H. Connelly | | | Chair | Member | | | Member | | Timothy S. Crane | | | | | | | Member | | Peter D. Crist | Chair | | Member | | Member | | Member | | William J. Doyle | Member | | | | Member | | | | Marla F. Glabe | | Member | | | | Member | | | H. Patrick Hackett, Jr. (Chair) | | | | | | | Chair | | Scott K. Heitmann | | | | Chair | | Member | Member | | Brian A. Kenney | | | | Member | | Member | | | Deborah L. Hall Lefevre | Member | | | | | Chair | Member | | Suzet M. McKinney | | | Member | Member | | | | | Gary D. “Joe” Sweeney | | Member | | | | Member | | | Karin Gustafson Teglia | | Chair | Member | | | | Member | | Alex E. Washington III | | | | | Chair | Member | Member | | Edward J. Wehmer | | | | | | | Member |

  5. Committee Membership

    The Nominating Committee has proposed, and the Board has agreed, that the membership of the Board and each of its committees following the Annual Meeting, assuming each Director nominee is elected, shall be as follows:

  6. Committee Membership

    | Board of Directors | Nominating and Corporate Governance Committee | Audit Committee | Compensation Committee | Risk Management Committee | Finance Committee | Information Technology/ Information Security Committee | Executive Committee | | Elizabeth H. Connelly | | | Chair | Member | | | Member | | Timothy S. Crane | | | | | | | Member | | Peter D. Crist | Chair | | Member | | Member | | Member | | William J. Doyle | Member | | | | Member | | | | Marla F. Glabe | | Member | | | | Member | | | H. Patrick Hackett, Jr. (Chair) | | | | | | | Chair | | Scott K. Heitmann | | | | Chair | | Member | Member | | Brian A. Kenney | Member | | | Member Vice Chair | | | | | Deborah L. Hall Lefevre | Member | | | | | Chair | Member | | Suzet M. McKinney | | Member | Member | | | | | | Gregory A. Smith* | | Member | | | Member | | | | Karin Gustafson Teglia | | Chair | Member | | | | Member | | Alex E. Washington III | | | Member | | Chair | | Member | | Edward J. Wehmer | | | | | | | |

  7. Committee Membership

    * Mr. Smith is a nominee for election to the Board at the Annual Meeting. Mr. Sweeney is not standing for re-election. The Board adopted the charter of each of the Nominating Committee, the Audit Committee, the Compensation Committee, the Risk Management Committee, the Finance Committee, the IT/IS Committee and the Executive Committee, copies of which are available at www.wintrust.com by choosing “Investor Relations” and then choosing “Corporate Governance.” Our Corporate Governance Guidelines are also available on the Company’s website under the same heading.

  8. DIRECTOR COMPENSATION

    DIRECTOR COMPENSATION The Company seeks to compensate its non-employee Directors in a manner that attracts and retains qualified candidates to serve on the Board and to compensate such Directors for their service on the Board in an amount that is commensurate with their role and involvement. In setting non-employee Director compensation, the Nominating Committee and the Board consider the significant amount of time the Directors expend in fulfilling their duties as well as the skill level required.

  9. 2023 Director Compensation Table

    2023 Director Compensation Table The table below summarizes the compensation paid by the Company to non-employee Directors for the fiscal year ended December 31, 2023.

  10. 2023 Director Compensation Table

    | (a) Name | (b) Fees Earned or Paid in Cash ($)(1) | (c) Stock Awards ($) | (d) Option Awards ($) | (e) Change in Pension Value and Nonqualified Deferred Compensation Earnings ($) | (f) All Other Compensation ($)(2) | (g) Total ($) | | Elizabeth H. Connelly | 207,420 | — | — | — | 3,799 | 211,219 | | Peter D. Crist | 188,800 | — | — | — | 111,914 | 300,714 | | William J. Doyle | 155,300 | — | — | — | 20,910 | 176,210 | | Marla F. Glabe | 156,800 | — | — | — | 11,903 | 168,703 | | H. Patrick Hackett, Jr. | 200,000 | — | — | — | 4,819 | 204,819 | | Scott K. Heitmann | 178,600 | — | — | — | 44,302 | 222,902 | | Brian A. Kenney | 153,600 | — | — | — | 1,182 | 154,782 | | Deborah L. Hall Lefevre | 180,300 | — | — | — | 15,960 | 196,260 | | Suzet M. McKinney | 157,000 | — | — | — | 4,500 | 161,500 | | Gary D. “Joe” Sweeney | 156,800 | — | — | — | 11,650 | 168,450 | | Karin Gustafson Teglia | 185,200 | — | — | — | 25,149 | 210,349 | | Alex E. Washington, III | 175,200 | — | — | — | 27,238 | 202,438 |

  11. 2023 Director Compensation Table

    Represents fees for services as non-employee Directors of the Company. During 2023, certain Directors elected to receive fees in Common Stock, in lieu of cash payments, as follows:

  12. 2023 Director Compensation Table

    | Name | Fees Earned in Common Stock ($) | | Elizabeth H. Connelly | 207,420 | | Peter D. Crist | 188,800 | | William J. Doyle | 155,300 | | Marla F. Glabe | 156,800 | | Scott K. Heitmann | 66,000 | | Brian A. Kenney | 153,600 | | Deborah L. Hall Lefevre | 180,300 | | Karin Gustafson Teglia | 185,200 | | Alex E. Washington, III | 175,200 |

  13. 2023 Director Compensation Table

    As of December 31, 2023, Directors held unissued Units under the Director Plan as follows: Ms. Connelly: 4,075 Units; Mr. Crist: 67,815 Units; Mr. Doyle: 14,541 Units; Ms. Glabe: 2,213 Units; Mr. Hackett: 3,052 Units; Mr. Heitmann: 14,678 Units; Mr. Kenney: 2,034 Units; Ms. Lefevre: 11,615 Units; Ms. Teglia: 12,736 Units; and Mr. Washington: 9,974 Units. Includes fees paid in cash and stock, both currently paid and deferred, for services as directors of the Company’s subsidiaries. Also includes dividends earned on fees deferred as described above. Directors with $10,000 or more in “All Other Compensation” for the fiscal year ended December 31, 2023 were: Mr. Crist ($104,464 in dividends earned and $7,450 in fees for service as a director of one of the Company’s subsidiaries); Mr. Doyle ($20,910 in dividends earned); Ms. Glabe ($1,303 in dividends earned and $10,600 in fees for service as a director or member of the executive advisory committee of five of the Company’s subsidiaries or divisions); Mr. Heitmann ($22,302 in dividends earned and $22,000 in fees for service as a director of four of the Company’s subsidiaries); Ms. Lefevre ($15,960 in dividends earned); Mr. Sweeney ($11,650 in fees for service as a director of one of the Company’s subsidiaries); Ms. Teglia ($17,549 in dividends earned and $7,600 in fees for service as a director of one of the Company’s subsidiaries); and Mr. Washington ($13,238 in dividends earned and $14,000 in fees for service as a director of one of the Company’s subsidiaries).

  14. PROPOSAL NO. 1 — ELECTION OF DIRECTORS

    PROPOSAL NO. 1 — ELECTION OF DIRECTORS The Company’s Board is currently comprised of 14 Directors, each serving a term that will expire at this year’s Annual Meeting or until a successor has been elected and qualified. 14 individuals are standing for election at the Annual Meeting to serve on the Board until the next Annual Meeting or until a successor has been elected and qualified. The Board, acting pursuant to the recommendation of the Nominating Committee, has nominated each incumbent Director, who are standing for election, other than Mr. Sweeney, who is not standing for election. Additionally, the Board, acting pursuant to the recommendation of the Nominating Committee, has nominated Gregory A. Smith for election to the Board. Each nominee has indicated a willingness to serve, and the Board has no reason to believe that any of the nominees will not be available for election. However, if any of the nominees is not available for election, proxies may be voted for the election of other persons selected by the Board. Proxies cannot, however, be voted for a greater number of persons than the number of nominees named. Shareholders of the Company have no cumulative voting rights with respect to the election of Directors. It is expected that, pending re-election at the Annual Meeting, H. Patrick Hackett, Jr. will continue serve as non-executive Chairman of the Board following the Annual Meeting. Assuming each Director nominee is elected to serve on the Board until the next Annual Meeting, the membership of the Board and each of its committees following the Annual Meeting, is expected to be as reflected in the following chart.

  15. PROPOSAL NO. 1 — ELECTION OF DIRECTORS

    | Name | Age At Annual Meeting | Director Since | Committees | Subsidiaries/Divisions | | Elizabeth H. Connelly | 59 | 2022 | Compensation (Chair) Risk Management Executive | — | | Timothy S. Crane | 62 | 2023 | Executive | Shared officer and advisory director of each subsidiary | | Peter D. Crist | 72 | 1996 | Compensation Finance Nominating (Chair) Executive | Hinsdale Bank | | William J. Doyle | 73 | 2017 | Finance Nominating | — | | Marla F. Glabe | 70 | 2015 | Audit IT/IS | Great Lakes Advisors Wintrust Investments The Chicago Trust Company FIRST Insurance Funding Wintrust Life Finance | | H. Patrick Hackett, Jr., Chairman of the Board | 72 | 2008 | Executive (Chair) | Wintrust Bank (Advisory Director) | | Scott K. Heitmann | 75 | 2008 | IT/IS Risk Management (Chair) Executive | Great Lakes Advisors Wintrust Investments The Chicago Trust Company Wintrust Bank | | Brian A. Kenney | 64 | 2023 | Nominating Risk Management (Vice Chair) | — | | Deborah L. Hall Lefevre | 56 | 2019 | IT/IS (Chair) Nominating Executive | — |

  16. PROPOSAL NO. 1 — ELECTION OF DIRECTORS

    | Name | Age At Annual Meeting | Director Since | Committees | Subsidiaries/Divisions | | Suzet M. McKinney | 51 | 2021 | Audit Compensation | Great Lakes Advisors Wintrust Investments The Chicago Trust Company | | Gregory A. Smith | 60 | — | Audit Finance | — | | Karin Gustafson Teglia | 56 | 2019 | Audit (Chair) Compensation Executive | Hinsdale Bank | | Alex E. Washington, III | 50 | 2020 | Finance (Chair) Compensation Executive | Wintrust Bank | | Edward J. Wehmer | 70 | 1996 | | |

  17. PROPOSAL NO. 1 — ELECTION OF DIRECTORS

    As indicated in the following matrix, based on each Director’s self-identified data, the Board is comprised of 36% women and 64% men, and includes two individuals (approximately 14% of the Board) who identify as members of a racial or ethnic minority group (African-American). None of the Directors have self-identified as LGBTQ+. This diversity information is the same for the 14 current directors and the 14 director nominees.

  18. PROPOSAL NO. 1 — ELECTION OF DIRECTORS

    | Board Diversity Matrix As of April 4, 2024 | | | | Total Number of Directors: | 14 | | | Part I: Gender Identity: | Female | Male | | Directors | 5 | 9 | | Part II: Demographic Background: | | | | African American or Black | 1 | 1 | | White | 4 | 8 |

  19. Nominees for Election at the 2024 Annual Meeting of Shareholders

    Nominees for Election at the 2024 Annual Meeting of Shareholders Elizabeth H. Connelly (59), Director since 2022. Ms. Connelly is Senior Vice President, Vertical Markets and a Member of the Executive Committee for CDW Corporation (Nasdaq) (“CDW”), a leading multi-brand technology solutions provider to business, government, education and healthcare organizations in the United States, the United Kingdom, and Canada. She has more than 30 years of experience in managing a spectrum of complex businesses, including human resources, commercial banking with a focus in the healthcare, higher education and not-for-profit sectors, and private wealth management. Ms. Connelly possesses a keen ability for building high-performing teams, fostering best-in-class culture, and delivering strong results. Before assuming her current role at CDW, Ms. Connelly was Chief Human Resources Officer and Senior Vice President of Coworker Services. She was responsible for leading the development and implementation of CDW’s talent strategy, including talent acquisition, employment branding, organizational and leadership development, sales training, compensation, benefits, diversity and inclusion, performance management and succession planning. Prior to joining CDW in 2018, Ms. Connelly served since 2012 as the Head of the Healthcare, Higher Education and Not-for-Profit Commercial Banking business unit at J.P. Morgan Chase, a leading global financial services firm, where she led business groups that were national in scope and provided treasury, credit and specialized industry solutions to more than 3,000 clients. Previously, she served as the firm’s Midwest Region Head for the Private Wealth Management business unit and, prior to that, she held several leadership roles in Capital Markets at Bank One. Additionally, Ms. Connelly serves as a director of the Catholic Extension Society and the Polk Bros. Foundation. She is also a trustee for the Shedd Aquarium, and she serves on the Board of Regents for Georgetown University. In addition, she is a member of the Economic Club of Chicago, The Chicago Network, the Executives Club of Chicago, the National Association of Corporate Directors, and the Women Corporate Directors Foundation. Ms. Connelly earned a bachelor’s degree in foreign service from Georgetown University and a master’s degree in business administration from Northwestern University’s Kellogg School of Management. Ms. Connelly’s experience in the banking industry, including service in several leadership roles at J.P. Morgan Chase and Bank One, provide her with knowledge of the financial services business, generally, and the business of community banking, in particular. Her experience in human resources at CDW provides her with insight into the attraction and retention of talent, including within the realm of diversity and inclusion, which is of importance to the Company. Timothy S. Crane (62), Director since 2023. Mr. Crane was appointed to serve as a Director of the Company in January 2023. He joined the Company in August 2008 and has held a series of executive management roles. Mr. Crane currently serves as President and Chief Executive Officer of the Company. Prior to the transition to his current role on May 1, 2023, Mr. Crane served as President of the Company since February 2020, after previously holding the title of Executive Vice President, Senior Market Head and Treasurer since February 2017, during which time he was responsible for oversight of Wintrust’s subsidiary banks, banking operations and treasury business. Previously, in January 2016, Mr. Crane was appointed to serve as Corporate Treasurer of the Company. Before joining the Company, Mr. Crane served as President of Harris Bankcorp (Harris Bank, Bank of Montreal) in Chicago, where he was employed for 24 years. He also serves on the boards of the Metropolitan Family Services and the Bank Administration Institute and serves as a Trustee of DePaul University. In addition, he serves as an Advisory Director for each of the Company’s main operating subsidiaries. Mr. Crane brings a wealth of knowledge to the Board of Directors relating to banking operations, regulations, financial management, and mergers and acquisitions. He is one of two members of the Board who is also an executive officer of the Company. As such, he provides views of the management of the Company and substantial insight into the operations of the Company. Peter D. Crist (72), Director since 1996. Mr. Crist served as the Company’s Chairman from 2008 to 2017. He currently is the Chair of the Nominating Committee. Mr. Crist founded Crist/Kolder Associates, an executive recruitment firm, which focuses on chief executive officer and director searches, in 2003 and has served since inception as its Chairman and Chief Executive Officer. From December 1999 to January 2003, Mr. Crist served as Vice Chairman of Korn/Ferry International (NYSE), the largest executive search firm in the world. Previously, he was President of Crist Partners, Ltd., an executive search firm he founded in 1995 and sold to Korn/Ferry International in 1999. Immediately prior thereto he was Co-Head of North America and the Managing Director of the Chicago office of Russell Reynolds Associates, Inc., the largest executive search firm in the Midwest, where he was employed for more than 18 years. He currently serves as a director of Northwestern Memorial Hospital, where he is Chair of the Nominating and Corporate Governance Committee. Mr. Crist is a director of Hinsdale Bank. Mr. Crist’s experience assisting companies with executive searches provides him with insight into the attraction and retention of Company personnel, an important concern of the Company. In addition, Mr. Crist’s experience as an executive of several large, Chicago-based businesses provides him with insight into the management and operational challenges and opportunities facing the Company in its markets. He also brings experience as the previous Chair of the Compensation Committee of Northwestern Memorial Hospital. Additionally, Mr. Crist’s experience as a director of Hinsdale Bank gives him valuable insight into the Company’s banking operations. William J. Doyle (73), Director since 2017. Mr. Doyle served as President and Chief Executive Officer of Potash Corporation of Saskatchewan (“PotashCorp”), one of the world’s largest fertilizer suppliers, for 15 years, and retired in July 2015. Mr. Doyle formerly served as President of the International Fertilizer Industry Association, a trade association representing the global fertilizer industry, and was a board member of Canpotex and the International Plant Nutrition Institute. Mr. Doyle is a graduate of Georgetown University in Washington, D.C., and retired as Chairman of the University’s Board of Directors in July 2021. He also currently serves on the board of the Big Shoulders Fund, a charity providing support to Catholic schools in the neediest areas of inner-city Chicago. Mr. Doyle’s experience as President and Chief Executive Officer of PotashCorp provides him with insight into the challenges of leading a large and complex global organization with key operations throughout the world, as well as an understanding of the operation and management of, and governance and regulatory considerations associated with, a large public company.

  20. Nominees for Election at the 2024 Annual Meeting of Shareholders

    Marla F. Glabe (70), Director since 2015. Ms. Glabe has over 40 years of experience in the financial services industry including her service as a senior executive with Allstate Insurance Company (“Allstate”) and as a member of the board of directors of Allstate Life Insurance Company. From 1974 to 2009, she held various executive positions at Allstate and its affiliates. Subsequently, Ms. Glabe served as the Lead Managing Director for MasterMind Advisory Board, a corporation offering advisory services to CEOs and business entrepreneurs and as a member of the Board of Directors for Royal Neighbors of America, a fraternal life insurance company. Ms. Glabe is Senior Advisor for Management Control International, Inc., a privately owned family asset management firm, serves as a director of Northwest Community Healthcare, and is a member of the Society of Actuaries. Ms. Glabe is a director of Great Lakes Advisors, Wintrust Investments, and The Chicago Trust Company and serves on the Executive Advisory Committee for First Insurance Funding and Wintrust Life Finance. Ms. Glabe’s business experience gives her in-depth knowledge of managing and providing leadership at sophisticated nationwide organizations in highly regulated businesses. Her knowledge of the insurance industry gives her insight into an area, which, through the Company’s insurance premium financing business, impacts a substantial portion of the Company’s business. In addition, her experience in leadership provides Ms. Glabe with knowledge of the issues faced by large and complex businesses in the financial services industry. As a result of her financial experience, Ms. Glabe qualifies as a financial expert for purposes of rules governing audit committees. Ms. Glabe’s experience on the Executive Advisory Committee for First Insurance Funding and Wintrust Life Finance and as a current director of the boards associated with Wintrust Wealth Management gives her valuable insight into the Company’s non-banking operations. H. Patrick Hackett, Jr. (72), Director since 2008. Mr. Hackett has served as the Company’s Chairman since 2017. Mr. Hackett has been the Managing Member of HHS Partners, LLC, an investment company located in the Chicago area, since 2001. Previously, he served for 12 years as the President and Chief Executive Officer of RREEF Capital, Inc. and as Principal of The RREEF Funds, an international commercial real estate investment management firm. Mr. Hackett serves as a Life Trustee of Northwestern University and taught real estate finance at the Kellogg Graduate School of Management for many years when he also served on the real estate advisory boards of Kellogg and of the Massachusetts Institute of Technology. He serves on the board of First Industrial Realty Trust, Inc. (NYSE) where he chairs the Investment and Compensation Committees. Mr. Hackett is an advisory director of Wintrust Bank. Mr. Hackett’s business and education backgrounds provide him familiarity with financial models and valuation of corporations and banks, as well as of commercial real estate, which often serves as collateral for the Company’s products. Mr. Hackett worked as a bank auditor early in his career, giving him some experience in bank accounting and operations. Scott K. Heitmann (75), Director since 2008. Mr. Heitmann, retired for the past 18 years, has over 32 years of experience in the banking industry, including his service as Vice Chairman of LaSalle Bank Corporation and President, Chairman and Chief Executive Officer of Standard Federal Bank from 1997 to 2005. He served as the President and Chief Executive Officer of LaSalle Community Bank Group and LaSalle Bank FSB from 1988 to 1996. Mr. Heitmann currently serves as an Advisory Director of Boys Hope Girls Hope of Illinois. Mr. Heitmann has previously served as a director of LaSalle Bank Corporation, Standard Federal Bank and the Federal Home Loan Bank of Chicago. Mr. Heitmann is a director of Great Lakes Advisors, Wintrust Investments, The Chicago Trust Company, and Wintrust Bank. Mr. Heitmann’s experience in the banking industry, including service in executive leadership roles at LaSalle Bank Corporation and Standard Federal Bank, provide him with knowledge of the financial services business, generally, and the business of community banking, in particular. His experience as a former bank lender also provides insight into the Company’s community banking business. In addition, his experience with LaSalle Bank’s various predecessors provides him with insight into the opportunities and challenges posed to a growth-oriented Chicago-based community bank. Mr. Heitmann’s experience as a director of Wintrust Bank and the boards associated with Wintrust Wealth Management gives him valuable insight into the Company’s banking, brokerage and investment advisory operations. Brian A. Kenney (64), Director since 2023. Mr. Kenney served as the Chairman, President and Chief Executive Officer of GATX Corporation (NYSE) (“GATX”), a global railcar lessor, from April 2005 until his retirement in April 2022. Previously, he held positions at GATX as President from 2004 to 2005, Senior Vice President, Finance and Chief Financial Officer from 2002 to 2004, Vice President, Finance and Chief Financial Officer from 1999 to 2002, and Vice President — Finance from 1998 to 1999. He first joined GATX in 1995 as Treasurer. Before his career at GATX, Mr. Kenney held various financial positions at AMR Corporation, United Airlines, and Morton International, Inc. He currently serves on the Board of Trustees of the Shedd Aquarium in Chicago, where he was Chairman from 2018 to 2022. Mr. Kenney also served as a member of the board of directors of USG Corporation, a publicly-held manufacturer and supplier of building supply products, from 2011 until its acquisition in April 2019. Mr. Kenney’s experience as Chairman, President and Chief Executive Officer of GATX provides him with the unique perspective that comes from leading a large, publicly-traded global business. In addition, his extensive financial and capital markets expertise gives him valuable insight into key functions of the Company. Deborah L. Hall Lefevre (56), Director since 2019. Ms. Lefevre joined Starbucks Corporation (Nasdaq) (“Starbucks”), which is an American multinational chain of coffeehouses and roaster, as Executive Vice President, Chief Technology Officer in May 2022. In her role, she is responsible for the company’s technology strategy and execution around the world for over 36,000 stores in 80 countries, 9,265 company-operated and 6,608 licensed stores located in the United States. From 2017 until joining Starbucks, she served as Executive Vice President, Chief Technology Officer of Couche-Tard/Circle K (“Circle K”), where she was responsible for global technology and digital strategy and execution across a network of approximately 15,500 locations operated by Circle K, a multinational operator of convenience stores. Before she joined Circle K in 2017, Ms. Lefevre served in several senior level management roles within the Information Technology department of McDonald’s Corporation, including Corporate Vice President, Global Enterprise Solutions and Business Transformation (2015 – 2017); Chief Information Officer, U.S. Segment (2013 – 2015); and Vice President, IT Enterprise (2008 – 2013). Ms. Lefevre’s extensive knowledge of information technology systems and cybersecurity risk management provides the Company with sophisticated guidance regarding the Company’s technology and information security strategy and tactical objectives. In addition, her experience as a senior executive of large, public companies provides her with comprehensive knowledge of the issues faced by highly-complex businesses.

  21. Nominees for Election at the 2024 Annual Meeting of Shareholders

    Suzet M. McKinney DrPH, MPH (51), Director since 2021. Dr. McKinney currently serves as Principal & Director of Life Sciences at Sterling Bay Company, LLC, a real estate development company, where she is responsible for relationships with the scientific, academic, corporate, tech and governmental sectors involved in the life science ecosystem, as well as managing the experience and facilitating the growth of life science tenants in Sterling Bay developments. Prior to joining Sterling Bay in February 2021, she served since September 2015 as executive director of the Illinois Medical District, which includes 560 acres of medical research facilities, labs, a biotech business incubator, universities, raw land development areas, four hospitals, and more than 40 healthcare-related facilities. It is one of the largest urban medical districts in the United States. Dr. McKinney currently serves as a director of the Company’s Wealth Management subsidiaries: Great Lakes Advisors, Wintrust Investments, and The Chicago Trust Company. Dr. McKinney has served as a member of the Board of Directors of Kemper Corporation (NYSE: KMPR), one of the nation’s leading specialized insurers, since February 7, 2024. She also currently serves as a board member of Thresholds, as well as the Ann & Robert Lurie Children’s Hospital of Chicago. Dr. McKinney holds her doctorate from the University of Illinois at Chicago School of Public Health. She received her bachelor’s degree in biology from Brandeis University, where she was also a Howard Hughes Fellow. Additionally, she received her master of public health degree, in health care administration, and certificates in managed care and health care administration, from Benedictine University. Dr. McKinney’s professional experience includes managing large and complex organizations, as well as extensive familiarity with the Chicago business community. Dr. McKinney’s experience as a director of Wintrust Investments, Great Lakes Advisors and The Chicago Trust Company gives her valuable insight into the Company’s non-banking operations. Gregory A. Smith (60), Director Nominee. Mr. Smith currently serves as an Executive-in-Residence and Professor of Practice at the University of Wisconsin-Milwaukee’s Lubar School of Business, a position he has held since 2012. He also serves as the Curriculum Director for the American Bankers Association’s Stonier Graduate School of Banking. Additionally, Mr. Smith serves as a Director of both Envestnet, Inc. (NYSE: ENV) (since 2015) and Church Mutual Holding Company, Inc. (since 2014). Prior to joining the University of Wisconsin-Milwaukee, Mr. Smith served as Senior Vice President and Chief Financial Officer of the Marshall & Ilsley Corporation and its subsidiary M&I Bank from 2006 until Marshall & Ilsley’s sale to BMO Harris Bank in 2011. Before working at Marshall & Ilsley, Mr. Smith worked in the investment banking industry with a focus on the financial services sector. Mr. Smith is an honors graduate of both Princeton University, where he received an undergraduate degree, and The University of Chicago, where he received an MBA. More recently, he has been recognized as a Board Leadership Fellow by the National Association of Corporate Directors. Mr. Smith’s experience in the banking and investment banking industries provide him with knowledge of the financial services business and capital raising and investment processes. Mr. Smith’s banking industry experience is expected to provide sophisticated insight with respect to the Company’s banking operations and his professional experience in Wisconsin provides valuable familiarity with one of the Company’s core banking markets. His experience also includes the management of liquidity, financial reporting and risk management of a multitude of large and complex organizations. As a result of his financial experience, Mr. Smith qualifies as a financial expert for purposes of rules governing audit committees. Karin Gustafson Teglia (56), Director since 2019. Ms. Teglia is President of DEKK Enterprises, LLC, an incubator that develops innovative concepts and go-to-market strategies for consumer products and services, and DEKK Investments, LLC. Ms. Teglia also has served since 2009 as an advisor to TRP Investments, LLC, a commercial real estate investor. Prior to this role, Ms. Teglia served in various corporate finance management and international tax roles within McDonald’s Corporation, including Corporate Senior Vice President, Finance (2007 – 2008); Corporate Vice President, Finance (2005 – 2007); and Corporate Vice President of Tax (2001 – 2005). Prior to joining McDonald’s Corporation in 1995, Ms. Teglia began her career as an international tax consultant with Price Waterhouse. Ms. Teglia is a certified public accountant and an attorney licensed to practice in Illinois. Ms. Teglia currently serves as a director of Hinsdale Bank, chairing its Audit Committee and also serving on its Risk Committee. She also served on an Advisory Panel of the National Academy of Sciences, focusing on food allergy research, and serves on the Food Allergy Research and Education Board of National Ambassadors. Ms. Teglia’s management experience at McDonald’s Corporation provides experience with the management of the liquidity, financial reporting, risk and audit management of a large organization. As a result of her financial experience, Ms. Teglia qualifies as a financial expert for purposes of rules governing audit committees. Additionally, Ms. Teglia’s experience as a director of Hinsdale Bank gives her valuable insight into the Company’s banking operations, as well as experience as an audit committee member and chair. Alex E. Washington, III (50), Director since 2020. Mr. Washington serves as a Managing Director of Wind Point Partners, a middle market private equity firm based in Chicago. Wind Point Partners has approximately $7.0 billion in assets under management and focuses on acquisition of middle-market companies in the industrial products, consumer products, and business services sectors. Mr. Washington joined Wind Point Partners in 2002 and currently serves on the boards of several private companies, including Quantix, Ascensus Specialties, Hardgards, and HASA. Past directorships include Argotec, Arr-Maz Custom Chemicals, Critica Infrastructure, Dicom Transportation Group, Evans Food Group, Kleinfelder Group, Novolex, and Paragon Films. Prior to Wind Point Partners, he held professional roles with J.H. Whitney, Donaldson Lufkin & Jenrette, and McKinsey & Company. Mr. Washington received a Bachelor of Arts in Finance from Morehouse College and a Master of Business Administration from Harvard Business School. Mr. Washington was a Class VI recipient of the Ewing Marion Kauffman Fellowship in venture capital. He currently serves as a director of Wintrust Bank, where he chairs its Audit Committee. His civic activities include serving as a board member of the Chicago Council on Global Affairs, board member of the Art Institute of Chicago, life trustee of the Chicago Foundation for Education, and member of both the Chicago Club and the Economic Club of Chicago.

  22. Nominees for Election at the 2024 Annual Meeting of Shareholders

    Mr. Washington’s extensive private equity experience provides him with comprehensive knowledge of mergers and acquisitions, capital raising, and the investment process, each of which are key functions of the Company. The Board believes that his knowledge of underwriting approaches and valuation methodologies is extremely valuable in evaluation of proposed transactions. Mr. Washington’s significant experience on the board of directors of other companies also provides him with familiarity with the management of the liquidity, financial reporting, risk and audit management of complex organizations. Additionally, Mr. Washington’s experience as a director of Wintrust Bank gives him valuable insight into the Company’s banking operations, as well as experience as a board committee member and chair within the Wintrust enterprise. Edward J. Wehmer (70), Director since 1996. Mr. Wehmer, a founder of the Company, has served as Founder and Senior Advisor and Executive Chairman of the Board of Directors since May 2023. Prior to May 2023, Mr. Wehmer served as Founder and Chief Executive Officer since February 2020. He also served as President and Chief Executive Officer of the Company from May 1998 to February 2020. Prior to May 1998, Mr. Wehmer served as President and Chief Operating Officer of the Company since its formation in 1996. He served as the President of Lake Forest Bank from 1991 to 1998. Mr. Wehmer is a certified public accountant and earlier in his career spent seven years with the accounting firm of Ernst & Young LLP specializing in the banking field and particularly in the area of bank mergers and acquisitions. Mr. Wehmer serves as Lead Independent Director on the board of directors of Stepan Company (NYSE), a chemical manufacturing and distribution company. He also serves as a director of the Catholic Extension Society, as a Life Trustee of Northwestern Memorial Health Care and of Ann & Robert H. Lurie Children’s Hospital and Foundation, as chair of Northwestern Memorial Hospital Foundation, and as the vice chairman of the Finance Council of the Archdiocese of Chicago. Mr. Wehmer is one of two members of the Board who is also an executive officer of the Company. As such, he provides substantial insight into the operations of the Company. As an employee of the Company since its inception, he also provides historical context for the Board’s discussions.

  23. Our Executive Compensation Practices

    | What We Do | What We Don’t Do | | ☑ We Pay for Performance: The majority of executive pay is not guaranteed. Our current CEO and our other NEOs (excluding Mr. Wehmer) on average have approximately 80% and 68%, respectively, of their target total compensation tied to Company performance through achievement of performance goals or our Common Stock price. | ☒ No Hedging or Short Selling: Our NEOs are prohibited from engaging in short selling of our Common Stock or engaging in hedging or offsetting transactions regarding our Common Stock. | | ☑ We Align Our Long-Term Incentives With Performance: The significant majority of our long-term incentive awards are performance-based. | ☒ No Pledging: Our NEOs are prohibited from pledging our securities. | | ☑ We Set Stretch Goals: Our performance hurdles are designed to require stretch individual and Company performance along with superior returns in order to receive commensurate payout. | ☒ No Excessive Expenditures or Perquisites: We have adopted a policy designed to prevent any excessive expenditures and maintain modest perquisites. | | ☑ We Have a Clawback Policy: In the event of a restatement of our financial statements, we are required to claw back payments made which were predicated on achieving certain financial results. | ☒ No Undue Risk: We discourage excessive risk taking by having a balanced portfolio of short- and long-term incentive performance measures and a cap on final payouts. | | ☑ We Require Stock Ownership: We have robust stock ownership guidelines. Our CEO is required to hold Common Stock with a value equal to a multiple of six times base salary. Our other NEOs are required to hold between one and three times base salary. | ☒ No Repricing Underwater Options: Our stock incentive plan does not permit repricing or the exchange of underwater stock options without shareholder approval. | | ☑ We Utilize Independent Compensation Expertise: The Committee has retained Meridian, an independent compensation consultant, to advise on the executive compensation program and practices, including annual assessments of the Company’s peer group. | ☒ No CIC Payment Absent a Double Trigger: Payments under our employment agreements and our long-term incentive programs require two events for vesting in connection with a change in control — both a change in control and a qualifying termination of employment. |

  24. Compensation Philosophy and Objectives

    Compensation Philosophy and Objectives The philosophy underlying our executive compensation program is to promote a pay-for-performance environment and remain competitive with market practices in order to attract and retain key talent, which we believe will support the long-term success of the Company and build value for our shareholders. The compensation elements included in the pay of our NEOs vary and are reflective of different pay objectives. Base salaries are intended to pay executives competitively relative to market peers and individual performance. Relevant performance factors that influence base pay include leadership, innovation, diversity initiatives, strategic contributions, maintaining effective company systems and infrastructure, customer service and talent management. Variable compensation (short-term and long-term incentives) is tied to financial measures (such as pre-tax net income, net interest margin, net overhead ratio, core loan and deposit growth, credit quality, and earnings per share) as well as the achievement of specific business objectives (including satisfactory regulatory exams), employee retention, and increased shareholder value. It is also the Committee’s philosophy to provide retirement and health and welfare benefits to all employees on a non-discriminatory basis. We do not provide supplemental retirement benefits to our executives. The Committee has set forth the following objectives for its executive compensation program: • Attract first-rate entrepreneurial talent that reflects our structure. We believe that our unique organizational design and structure are a significant part of our value proposition. Consequently, we need to hire leaders who will thrive within our matrixed organizational structure which allows the capacity to act in equal measure autonomously at times and in collaboration at times, while driving growth and managing risk. • Focus on performance-based compensation. Our compensation program is designed to support performance and achievement at every level of the organization, from the individual to the bank, subsidiary and Company. It is also designed to drive performance across both short-term and long-term horizons. • A significant portion of total compensation should be in the form of long-term incentives. Our compensation program includes incentives designed to align management and shareholder interests over a multi-year performance and vesting period. This longer-term horizon also helps promote retention and therefore business continuity. Long-term incentive compensation should balance growth and risk. Our longer-term rewards are structured to help mitigate excessive risk-taking since leaders are rewarded for creating sustained value for the Company and its shareholders. Long-term incentive compensation should be highly correlated with returns. The prescribed performance goals under our long-term incentive compensation program are designed to be challenging, and at or above target payouts should be achievable only with above target, superior organizational performance. Further, the use of total shareholder return as a long-term incentive metric is intended to directly link NEO and shareholder interests. • Compensation levels should be competitive to enable us to attract and retain a highly qualified management team to lead and grow our Company. The successful operation of our Company requires an experienced and talented management team. We hire for both the current and anticipated future needs of the organization, so executives must be able to effectively lead the organization now, and also meet future needs of a growing organization. To do this, our compensation program must be competitive with those of our peer firms to attract and retain talent that is capable of scaling for the future. • Compensation opportunities should be commensurate with an executive’s roles and responsibilities. Our organization values talented executives who perform comprehensively, both within their specific roles as well as taking on more leadership responsibilities. Consequently, our compensation program seeks to recognize and reward our executives who are most responsible for the performance of the Company and who engage in broader duties than their job titles may imply. • Compensation for NEOs should be fair and perceived as such, both internally and externally. We measure the appropriateness of our compensation offerings by comparing them both internally and externally to peer group benchmarks. Shareholders are best served when we can attract and retain talented executives with compensation packages that are competitive with organizations similar in size, scope and complexity to Wintrust.

  25. Peer Group Benchmarking

    Peer Group Benchmarking On an annual basis, the Committee’s independent compensation consultant, Meridian Compensation Partners, LLC (“Meridian”), provides the Committee with assessments of the competitive market and best practices relating to executive compensation practices, including peer group development, executive and board benchmarking, executive pay-for-performance analysis, research on regulatory and industry trends, and program design. The Committee utilizes these assessments and references when considering compensation program design and other decisions. Peer Group Analysis On an annual basis, the Committee engages Meridian to review the peer group to evaluate whether it reflects the appropriate population of banks both regionally and nationally similar to Wintrust in size, scope and complexity. When identifying and constructing the competitive peer group, the Committee took into consideration which companies compete for customers, executive talent or investors, as well as other factors including the amount of commercial and industrial loans, level of non-interest revenue, and comparability in business models. These factors were considered as the Committee sought to develop a peer group that approximated the size and the structure of the Company. The following peer group, developed in 2022 and used by the Committee to help guide 2023 compensation decisions, was comprised of 18 banks, including 14 similarly-sized national banks and four Midwestern banks. This reference group of banks had assets between $30 billion and $109 billion as of March 31, 2022, with Wintrust’s assets then positioned at approximately the median.

  26. Peer Group Benchmarking

    | National Holding Company Peer Group* | | | | BOK Financial Corporation | First Horizon Corporation | Western Alliance Bancorporation | | Cadence Bank | Pinnacle Financial Partners, Inc. | Zions Bancorporation, N.A. | | Comerica Incorporated | Synovus Financial Corp. | | | Cullen/Frost Bankers, Inc. | Texas Capital Bancshares, Inc. | | | F.N.B. Corporation | Valley National Bancorp | | | First Citizens BancShares, Inc. | Webster Financial Corporation | |

  27. Peer Group Benchmarking

    | Midwestern Holding Company Peer Group | | | Associated Banc-Corp | Old National Bancorp | | Commerce Bancshares, Inc. | UMB Financial Corporation |

  28. Peer Group Benchmarking

    The peer group used for purposes of 2023 compensation decisions was updated (as compared to the peer group used for 2022 compensation decisions) to eliminate CIT Group, Inc., First Midwest Bancorp, Inc., People’s United Financial, Inc., BankUnited, Inc. and Hancock Whitney Corporation and to add Cadence Bank, Old National Bancorp and Pinnacle Financial Partners Inc., based on the peer group selection criteria described above. When making compensation decisions, the Committee generally reviews the compensation paid to our CEO and other NEOs relative to the compensation paid to similarly-situated executives, to the extent available, at our peer companies based on publicly available information reported in our peers’ proxy statements. Benchmark Analysis In December 2022, Meridian provided the Committee with background information regarding the Company’s compensation structure as compared to the peer group and market practices. Meridian provided the Committee with an analysis undertaken with respect to each of the NEO’s positions, including a comparison of target total compensation, target total direct compensation as well as each component of compensation (e.g., base salary, short-term incentives, long-term incentives, benefits) on a comparative basis with the Company’s peer group. In addition, the Committee reviewed NEO compensation in the aggregate to that of our peer group. The Committee believes that reviewing compensation across both dimensions of their role and in aggregate provides the Committee with the most well-rounded view of the appropriateness of NEO compensation levels relative to peers. Pay-for-Performance Analysis Each year, Meridian conducts a pay-for-performance analysis which compares realized and realizable pay for the CEO as compared to the chief executive officers in our peer group. This analysis provides a retrospective look which evaluates the historical relationship between pay and performance, the effectiveness of the Company’s pay structures and performance goals and whether pay was aligned with performance. The 2023 study reviewed pay and performance over the prior three-year period (2020-2022) and found that the Company’s historical performance and the CEO’s actual pay results were reasonably aligned (referring to Mr. Wehmer in this instance). The Committee intends to continue to monitor the effectiveness of the Company’s executive pay program and alignment of pay with performance.

  29. 2023 Compensation Elements and Decisions

    | Element | Key Characteristics | Why We Pay this Element | How We Determine the Amount | 2023 Decisions | | Annual Short-Term Incentive | Variable compensation component payable in cash or stock. Performance is 75% allocated to financial measures and 25% allocated to individual performance goals. Payment is capped at 150% of target. | Motivate and reward executives for performance on key operational, financial and individual objectives met during the course of the performance year. | Market practices and individual performance with actual payouts based on the extent to which performance goals are achieved. | Annual 2023 short-term incentive payouts ranged from 91.5% to 94.2% of target, based on a combination of Company and individual performance. This range excludes Mr. Wehmer’s short-term incentive payout, which pursuant to the Wehmer Agreement was an amount equal to 100.1% of his target, prorated for his time in position as CEO during 2023. | | Long-Term Incentives | Variable compensation component payable in performance-based restricted stock units and time-vested restricted stock units. Payments of performance-based awards are capped at 150% of target. | Align long-term interests of management and shareholders. Retain executive talent. | Market practices and individual performance, with actual value of the award impacted by our stock price performance and, in the case of performance-based restricted stock units, achievement of the underlying performance goals. | The 2023 LTIP consisted of a mix of awards (60% performance-based restricted stock units and 40% time-based restricted stock units). Vesting of the performance-based awards are determined after the 3-year performance period (2023-2025), with half of performance-based shares vesting based upon Adjusted EPS (as defined below) (30% of LTIP award) and half based upon Relative TSR (as defined below) (30% of LTIP award). The time-based restricted stock units awarded to NEOs cliff vest at the conclusion of the three-year vesting period. For a discussion of performance results and Committee decisions relative to the 2021-2023 LTIP performance period, please see “2023 LTIP Target and Grants” on page 49. | | Perquisites and Other Personal Benefits | Compensation component to provide basic competitive benefits. | Provide a base level of competitive compensation for executive talent. | Periodic assessment of competitive offerings. | The perquisites and other personal benefits range from approximately 1% to 2% of the total 2023 target compensation for each NEO. |

  30. 2023 Compensation Elements and Decisions

    * Mr. Wehmer’s 2023 base salary was $1,175,000 from January 1 through April 30, 2023, during which time he served as CEO. His 2023 base salary decreased to $450,000 on May 1, 2023, pursuant to the Wehmer Agreement, in connection with his transition to the role of Founder and Senior Advisor. Mr. Crane’s base salary increased to $1,000,000 on January 26, 2023, in connection with the planned CEO transition. Annual Short-Term Incentive The Company’s performance-based annual short-term incentives are based on each NEO’s overall performance and the achievement of Company performance goals subject to the discretion and adjustment by the Committee. Annual short-term incentives are intended to provide officers across the Company with an opportunity to receive cash compensation (which may be paid in equity at the discretion of the Committee), based on consideration of the Company, subsidiary and individual performance goals. Performance-based incentives are a key component of our total compensation package because they reward our executives for pursuing objectives that the Committee believes are consistent with the overall goals and strategic direction that the Board has set for the Company. NEO short-term incentive target opportunities are reviewed by the Committee annually to evaluate appropriateness to the current business cycle and competitiveness relative to the market. In determining the target annual short-term incentives, the Committee considers several factors, including: • market practices; • the target annual incentive set and achieved in recent years; • the desire to provide, as described above, a substantial portion of total compensation as performance-based; and • the relative importance and degree of difficulty of the short-term and long-term performance goals of the Company. The Committee establishes target opportunities for each participant based on their role and competitive market data. The 2023 target opportunities for the NEOs did not change as compared to the 2022 target opportunities other than Mr. Crane’s target opportunities, which were adjusted in connection with his assumption of the CEO role. Based on the Committee’s assessment of Corporate and individual performance, actual awards can vary from 0% to 150% of the target opportunities.

  31. 2023 Compensation Elements and Decisions

    The target for Mr. Wehmer was prorated for the time he was in position as CEO during 2023 and pursuant to the Wehmer Agreement, he did not participate in the annual short-term incentive program following his assumption of the Founder and Senior Advisor role on May 1, 2023. Consistent with 2022, the 2023 target annual short-term incentive opportunity was allocated in the following manner based upon the executive’s role: • 75% based on Company performance, associated with consolidated pre-tax net income; and • 25% based on individual goals and objectives. Based upon the weighting outlined above of the 75/25 allocation of the short-term incentive target, the table below reflects each NEO’s 2023 base salary and how their total incentive targets were allocated as a percentage of each NEO’s base salary.

  32. 2023 Compensation Elements and Decisions

    | Named Executive Officer | 2023 Base Salary | 2023 Total Short-Term Incentive Percentage at Target | Percentage Allocated to Company Performance | Percentage Allocated to Individual Objectives | | Edward J. Wehmer | $1,175,000* | 125% | 93.75% | 31.25% | | Timothy S. Crane | $1,000,000 | 125% | 93.75% | 31.25% | | David A. Dykstra | $850,000 | 80% | 60.00% | 20.00% | | Richard B. Murphy | $650,000 | 80% | 60.00% | 20.00% | | David L. Stoehr | $540,000 | 70% | 52.50% | 17.50% | | Kathleen M. Boege | $485,000 | 70% | 52.50% | 17.50% |

  33. 2023 Compensation Elements and Decisions

    * Mr. Wehmer’s 2023 base salary was $1,175,000 from January 1 through April 30, 2023, during which time he served as CEO. His 2023 base salary decreased to $450,000 on May 1, 2023, pursuant to the Wehmer Agreement. His short-term incentive target for 2023 was based on his initial 2023 base salary of $1,175,000 and his short-term incentive award for 2023 was prorated to reflect his service as CEO through April 30, 2023. Development of Company Performance Objectives The Committee considers a number of performance factors in determining short-term incentive awards, including key performance indicators such as net interest margin, net overhead ratio, loan, asset and deposit growth and credit quality, as well as qualitative factors including advances in the Company’s efforts to maintain a diverse and inclusive corporate culture, development of enterprise infrastructure that will support future growth, and continued business line diversification. One of the key Company-level objectives for 2023 was to achieve consolidated pre-tax net income of $1,032.9 million, consistent with the Board-approved 2023 budget. The Committee used the following guidelines to set the high, target, low, and threshold portion of the annual short-term incentive award opportunity allocated to the Company-level objective:

  34. 2023 Compensation Elements and Decisions

    | Wintrust 2023 Consolidated Pre-Tax Net Income | Performance Measurement of Company- Level Annual Short-Term Incentive Award | | Greater than $1,032.9 million | High | | $1,032.9 million | Target | | $929.6 million to $1,032.9 million | Low | | $723.0 million to $929.6 million | Threshold |

  35. Kathleen M. Boege

    Kathleen M. Boege • Manage legal matters and associated risk mitigation across the Company enterprise, in collaboration with cross-functional senior leadership team. • Oversee management of the Company’s litigation on a cost-effective basis. • Manage legal support of the Company’s transactional and strategic initiatives. • Collaborate with Human Resources leadership on strategic workforce initiatives. • Support the Company’s diversity, equity and inclusion initiatives, by providing legal advice and serving as executive sponsor of Women of Wintrust, the Company’s largest BRG. • Coordinate annual cadence of Board meetings and initiatives, including annual proxy solicitation and annual meeting of shareholders. Performance Results and Payouts As noted above under “2023 Business Highlights,” the Committee considered the Company’s strong performance during a year of challenges including rapidly rising interest rates, reflecting the benefit of the skill and guidance provided by the Company’s executive leadership team. Company Performance Results: The Company’s consolidated pre-tax net income for the year ended December 31, 2023 was $845.1 million. In determining the actual annual short-term incentive for each NEO associated with the achievement of Company-level objectives, the Committee considered a number of factors, including the following achievements: the Company achieved 90% of the consolidated pre-tax net income objective, after adjusting for factors including the special assessment of $34 million imposed by the Federal Deposit Insurance Corporation during the fourth quarter of 2023 in connection with the failure of several regional banks in early 2023 and a favorable variance of loan net charge-offs relative to the 2023 budget; • strong achievement measured against our key performance indicators, including net interest margin, net overhead ratio, loan, asset and deposit growth and credit quality; • enhanced focus on issues of diversity and inclusion within the Company’s workforce, including the second cohort of a 12-month advocate-protégé partnership program which paired select high-potential protégés with senior executive advocates. The protégé cohort included over 60% women and 35% leaders of color; • continued progress on diversification strategy via expanded lines of business; and • continued build out of enterprise infrastructure to support future success of the organization. The Committee, taking into account the Company’s actual consolidated pre-tax net income performance along with all of the other above-referenced positive key performance indicators, determined to pay out the portion of annual short-term incentives associated with the Company-level results at 90% of target. The Committee also took into account satisfaction of individual performance objectives. The Committee’s analysis ultimately resulted in short-term incentive payouts to NEOs other than Mr. Wehmer ranging from 91.5% to 94.2% of target and Mr. Wehmer’s prorated short-term incentive payout at 100.1% of target. Individual Performance Objectives: The Committee reviewed each executive’s performance relative to individual goals and determined that each of the NEOs achieved or exceeded all of their individual performance objectives. Total Annual Short-Term Incentive Payout: Consistent with the approach taken in prior years, the final determination of an NEO’s actual short-term incentive payment was based on the Committee’s holistic evaluation of Company and individual performance metrics including consolidated pre-tax net income, individual performance objectives, and discretionary factors. The Committee retains the discretion to determine the amount of any annual short-term incentive awarded to an NEO. The final determination of the Committee could result in no short-term incentive being paid or a short-term incentive amount above or below a strictly formulaic view of performance. Based on their analysis, the Committee approved the annual short-term incentive award for each NEO. The extent of achievement of Messrs. Crane and Wehmer and the other NEOs relative to the accomplishment of the Company’s financial objectives was taken into account. Additionally, short-term incentives were informed by the Committee’s intention to ensure that total cash compensation was at an appropriate competitive position relative to the Company’s performance. The following table sets forth the total eligible annual short-term incentive amounts at target and annual short-term incentives actually paid to each of our NEOs under the 2023 NEO short-term incentive program.

  36. Kathleen M. Boege

    | Named Executive Officer | Total Annual Short-Term Incentive at Target | Total Annual Short-Term Incentive Paid | % Annual Short-Term Incentive Paid vs. Target | | Edward J. Wehmer* | $489,583 | $490,000 | 100.1% | | Timothy S. Crane | $1,250,000 | $1,144,094 | 91.5% | | David A. Dykstra | $680,000 | $625,000 | 91.9% | | Richard B. Murphy | $520,000 | $480,000 | 92.3% | | David L. Stoehr | $378,000 | $355,974 | 94.2% | | Kathleen M. Boege | $339,500 | $314,000 | 92.5% |

  37. Kathleen M. Boege

    | Award Vehicle Mix | % of Award | | Performance-Based Restricted Stock Units | 60% | | Time-Based Restricted Stock Units | 40% |

  38. Kathleen M. Boege

    Performance-based restricted stock units and time-based restricted stock units are designed to promote pay for performance since the awards vest after three years and the performance-based stock awards vest based on the achievement of certain performance conditions. Performance-based awards under the LTIP are contingent upon the achievement of pre-established long-term goals set in advance by the Committee with results measured over a multi-year performance period (i.e., three years). Each year, the Committee sets three- year performance goals for the LTIP, which results in overlapping performance cycles. Performance-based awards are earned only at the end of the performance period based on the Company’s actual performance against pre-established goals certified by the Committee, subject to negative discretionary adjustments. In 2023, the Committee selected the following award mix for the 2023-2025 LTIP performance period: • 30% in performance-based restricted stock units, with vesting based on a measurement of earnings per share, as adjusted to exclude income taxes, acquisition-related charges and the provision for credit losses, with such amount being further reduced by actual net charge-offs of loans, over the performance period (“Adjusted EPS”); • 30% in performance-based restricted stock units, with vesting based on the Company’s Total Shareholder Return relative to the KBW Regional Bank Index (“KRX Index”) over the performance period (“Relative TSR”); and. 40% in time-based restricted stock units with vesting three years from the grant date (i.e., cliff vest on the third anniversary of the grant date). When it determined stock-based compensation LTIP awards for the 2023-2025 performance period in January, 2023, the Committee believed that the targets established for these performance metrics were reasonably achievable with strong executive management performance. Actual performance will be measured against the Adjusted EPS metric, with 50% vesting at the end of the performance period for achievement of threshold Adjusted EPS, 100% for achievement of target Adjusted EPS and 150% for achievement of maximum Adjusted EPS levels (with linear interpolation in the payout between performance levels). Adjusted EPS threshold, target and maximum performance measures have been designed to be challenging but achievable through strong management performance and successful execution of our operating plan. Relative TSR will measure our performance compared to the KRX Index with 50% vesting at the end of the performance period for achievement of the 25th percentile, 100% vesting for median percentile performance and 150% vesting for 75th percentile performance (with linear interpolation in the payout between performance levels). In 2023, the Committee also selected a time-based restricted stock unit award to comprise the remaining 40% of the overall LTIP award mix. The time-based restricted stock unit award has a three-year cliff vesting period. The Committee believed that an element of the overall stock-based awards should have a time-based component to create a balance between risk and executive management’s long-term focus on the Company’s overall achievement over the three years reflected in the appreciation of the Company’s stock price. 2023 LTIP Target and Grants: The Committee provided a 2023 LTIP grant for the performance period from January 1, 2023 through December 31, 2025, based on a target opportunity developed based on market practice, input from Meridian and our desire to provide a significant portion of compensation in long-term equity-based incentives. Additionally, given the unique circumstance of the CEO transition in 2023, the Committee used its discretion to increase the LTIP target for certain NEO, solely for the 2023-2025 performance period. The annual target LTIP award was increased by 30% for each of Messrs. Dykstra, Murphy and Stoehr and Ms. Boege, in consideration of their continued retention and leadership continuity through the CEO transition period, and to reward these NEOs for continuing strong performance during a period of significant change. Total target award opportunities are defined as a percentage of base salary and summarized in the table below, with 60% of the grant value provided as performance-based restricted stock units and 40% of the grant value provided as time-based restricted stock units. The ultimate value of the performance-based awards will depend on the Company’s performance relative to three-year goals and, in the case of both the performance-based and the time-based restricted stock units, the Company’s stock price at vesting. Each NEO’s long-term incentive target percentage, as a percentage of base salary, is outlined below.

  39. Kathleen M. Boege

    * Pursuant to the Wehmer Agreement, Mr. Wehmer was not eligible for a 2023 LTIP grant. Performance-Based Restricted Stock Unit Awards and Time-Based Restricted Stock Unit Awards: The performance-based restricted stock unit awards (60% of incentive target opportunity) will each be measured and vest following the end of the performance period ending December 31, 2025, and time-based restricted stock unit awards (40% of target incentive opportunity) will vest three years from the date of the award. The threshold, target and maximum award opportunities for each NEO for the performance-based restricted stock unit awards, and the number of time-based restricted stock units awarded to each NEO, are set forth in the following two tables: Performance-Based Restricted Stock Unit Awards

  40. Kathleen M. Boege

    2021-2023 LTIP Results and Payment: The 2021-2023 LTIP award consisted of three different payment vehicles: • 30% of the award in performance-based restricted stock units, with vesting based on Adjusted EPS • 30% of the award in performance-based restricted stock units, with vesting based on Relative TSR • 40% of the award in time-based vested restricted stock units The following tables outline the payout matrix adopted in conjunction with the 2021-2023 LTIP for the three-year Adjusted EPS and Relative TSR through December 31, 2023:

  41. Kathleen M. Boege

    | | Adjusted EPS over 3 year Performance Period | | Payout% of Target Award** | | Maximum | | 29.54 | 150% | | Target | | 23.63 | 100% | | Threshold | | 17.73 | 50% | | <Threshold | <$ | 17.73 | 0% |

  42. Kathleen M. Boege

    | | Relative TSR Percentile* | Payout % of Target Award** | | Maximum | 75th | 150% | | Target | 50th | 100% | | Threshold | 25th | 50% | | <Threshold | <25th | 0% |

  43. Kathleen M. Boege

    * Wintrust included within the Peer Group for purposes of determining relative ranking. ** Linear increase in payout between the performance levels if Threshold performance is achieved. For the 2021-2023 performance period the results for the Adjusted EPS and Relative TSR performance measures were in excess of the $29.54 maximum amount and the 94th percentile, respectively. Based on these levels of achievement, the Committee certified vesting of performance-based restricted stock units at 150% of target for each measurement, which performance-based restricted stock units vested on February 28, 2024. Based upon the weighting outlined above of the 30/30/40 allocation of the long-term incentive, the table below reflects the value of each NEO’s vested performance-based and time-based restricted stock units for the 2021-2023 performance period.

  44. Kathleen M. Boege

    | Named Executive Officer | Value of Performance-Based Restricted Stock Unit Settlement(1) | Value of Time-Based Restricted Stock Unit Settlement(2) | Total Value Delivered | | Edward J. Wehmer | $3,531,805 | $1,595,917 | $5,127,722 | | Timothy S. Crane | $652,574 | $294,891 | $947,465 | | David A. Dykstra | $961,042 | $434,269 | $1,395,311 | | Richard B. Murphy | $723,849 | $327,063 | $1,050,912 | | David L. Stoehr | $518,203 | $234,111 | $752,314 | | Kathleen M. Boege | $442,839 | $200,059 | $642,898 |

  45. Post-Termination Compensation

    Post-Termination Compensation We have entered into employment agreements with each of our NEOs that provide for post-termination compensation. These agreements provide for payments and other benefits if the NEO’s employment terminates for a qualifying event or circumstance, such as being terminated without “Cause” or leaving employment for “Constructive Termination,” as these terms are defined in the employment agreements. Additionally, the employment agreements provide for the payment of enhanced severance benefits if the NEO’s employment is terminated within eighteen months of a “Change-in-Control” (as defined in the agreements). Additional information regarding the employment agreements, including a definition of key terms and a quantification of benefits that would have been received by our NEOs had termination occurred on December 31, 2023, is found under the heading “Potential Payments upon Termination or Change in Control” on page 59 of this Proxy Statement. The Committee believes that these employment arrangements are an important part of overall compensation for our NEOs and will help to secure the continued employment and dedication of our NEOs, prior to or following a change in control, notwithstanding any concern that they might have at such time regarding their own continued employment. These agreements also contain restrictive covenants, including non-compete and non-solicitation provisions, which protect the Company’s interests in its client and employee relationships. The Committee also believes that these agreements are important as a recruitment and retention device, as nearly all of the companies with which we compete for executive talent have similar agreements in place for their senior employees.

  46. Additional Information Regarding Compensation Policies

    Additional Information Regarding Compensation Policies We have additional compensation policies that support our practices. These policies serve to further illustrate and provide context around our approaches to compensation. Clawback Policy. Our clawback policy provides that the Company will recover any payment or equity awards made to a current or former executive officer, if the payment was predicated upon achieving certain financial results that were subsequently the subject of a restatement. In such event, the Company will recover the amount by which any annual or long-term payments or awards made or granted exceeded what would have been awarded or granted based on restated financials. In addition, the Company may recover any profits realized on the sales of securities received by such executive officer pursuant to such awards. In 2023, the Company modified its clawback policy, in order to comply with recent requirements of U.S. Securities and Exchange Commission rules and Nasdaq Stock Market listing standards implementing Section 954 of the Dodd-Frank Wall Street Reform and Consumer Protection Act of 2010. In addition, the clawback provision of the Sarbanes-Oxley Act of 2002 also applies to Messrs. Wehmer, Crane and Stoehr. This provision provides that if the Company is required to restate its financial statements as a result of misconduct, Mr. Wehmer and Mr. Stoehr are required to reimburse the Company for short-term incentives or other incentive-based or equity-based compensation and profits realized in the 12 months after the financial information was first publicly issued or filed with the SEC. Policy Regarding Excessive or Luxury Expenditures. Our Board adopted a policy designed to eliminate or prevent any excessive or luxury expenditures, including excessive expenditures on entertainment or events, office and facility renovations, aviation or other transportation services. A copy of this policy is available on our website, www.wintrust.com. Tax Gross-Up Provisions. Effective May 20, 2009, the Company adopted a policy that it will not enter into any new or materially amended agreements with NEOs that include any excise tax gross-up provisions with respect to payments contingent upon a change in control. In connection with the CEO transition, Mr. Wehmer’s employment agreement was amended and restated to eliminate Mr. Wehmer’s contractual right to an excise tax gross-up with respect to change in control payments. Prohibition on Hedging and Short Selling. The Company’s employees, including its executive officers and Directors, are prohibited from engaging in short selling of the Common Stock or engaging in hedging or offsetting transactions regarding the Common Stock. Prohibition on Pledging Stock. In April 2013, the Company adopted a policy prohibiting executive officers and Directors from pledging any of the Company’s securities. Stock Ownership Guidelines. The Company has adopted stock ownership guidelines for our executive officers as part of our commitment to corporate governance and to strengthen the alignment of interests between our executive officers and shareholders. Under the guidelines, our CEO and other NEOs are expected to accumulate shares of Common Stock to meet the applicable ownership level within five years of their election or appointment. For purposes of the guidelines, “shares” include shares owned by the executive or the executive’s immediate family members residing in the same household, including shares held in the Company’s 401(k) plan or employee stock purchase plan, shares held in trust for the benefit of the executive or the executive’s family, shares obtained through stock option exercises, deferred shares, shares of time-based restricted stock and restricted stock units granted under the Company’s equity plans. Unvested performance-based restricted stock units and unexercised stock options are not counted as “shares” under the guidelines.

  47. Compensation Process and Roles

    Compensation Process and Roles Role of Management. The Committee made all 2023 compensation decisions for our NEOs. Mr. Crane annually reviews the performance of each of the Company’s and its subsidiaries’ officers (other than Mr. Crane and Mr. Wehmer whose performance is reviewed by the Committee). The conclusions reached and the compensation recommendations based on these reviews, including with respect to salary adjustments and incentive award amounts, were presented to the Committee. The Committee exercised its discretion in modifying any recommended adjustment or award. Committee Process. During 2023, the Committee reviewed both the Company’s compensation philosophy and the actual compensation being paid by the Company. The Committee met, including in executive sessions without any members of management present, to discuss, evaluate and set executive officer compensation. In determining compensation for each of the NEOs, the Committee focused on the total compensation received by each NEO, as well as the allocation of each element of compensation in relation to those provided by the peer companies identified above. The Committee acted pursuant to a written charter that had been approved by our Board. Compensation Consultant. The Committee has the sole authority to retain and dismiss its own outside compensation consultants and any other advisors it deems necessary. The role of a compensation consultant is to assist the Committee in analyzing executive compensation packages and to provide the Committee with information regarding market compensation levels, general compensation trends and best practices. The consultant also provides advice regarding the competitiveness of specific pay decisions and actions for the NEOs, as well as the appropriateness of the design of the Company’s executive compensation program. In 2021, 2022 and 2023, the Committee engaged Meridian to advise it on executive compensation-related issues, conduct benchmarking and pay-for-performance analyses and to provide advice relating to establishing bonus opportunities and target incentives for 2023. In addition, Meridian provided guidance on leading practices on compensation as well as an analysis of director compensation. Meridian attended meetings of the Committee, including executive sessions, upon invitation. Meridian did not provide any other services to the Company. The Committee has assessed the independence of Meridian pursuant to the rules of the SEC and concluded that Meridian’s work for the Committee does not raise any conflicts of interest.

  48. 2023 Summary Compensation Table

    2023 Summary Compensation Table The following table summarizes compensation awarded to, earned by or paid to our NEOs for 2023 and, to the extent required by SEC disclosure rules, 2022 and 2021. Compensation reflected for Mr. Wehmer for 2023 reflects his service as Chief Executive Officer from January 1 through April 30, 2023, and his subsequent service as Founder and Senior Advisor from May 1 through December 31, 2023. Compensation for Mr. Crane for 2023 reflects his service as President from January 1 through April 30, 2023, and his subsequent service as President and Chief Executive Officer from May 1 through December 31, 2023. The section of this Proxy Statement entitled “Compensation Discussion & Analysis” describes in greater detail the information reported in this table and the objectives and factors considered in setting NEO compensation.

  49. 2023 Summary Compensation Table

    | Name and Principal Position (a) | Year (b) | Salary ($) (c) | Bonus ($)(1) (d) | Stock Awards ($)(2) (e) | Option Awards ($) (f) | Non-Equity Incentive Plan Compensation ($) (g) | Change in Pension Value and Nonqualified Deferred Compensation Earnings ($) (h) | All Other Compensation ($)(3) (i) | Total ($) (j) | | Edward J. Wehmer Founder and Senior Advisor & Executive Chairman of the Board and Former Chief Executive Officer | 2023 | 700,962 | 490,000 | — | — | — | — | 2,409,840 | 3,600,802 | | | 2022 | 1,175,000 | 1,835,000 | 2,878,750 | — | 1,454,750 | — | 198,589 | 7,542,089 | | | 2021 | 1,172,596 | 3,382,462 | 2,530,000 | — | — | — | 55,254 | 7,140,312 | | Timothy S. Crane, President and Chief Executive Officer | 2023 | 965,533 | 1,144,094 | 2,750,000 | — | — | — | 33,853 | 4,893,480 | | | 2022 | 606,000 | 600,000 | 712,500 | — | 239,487 | — | 28,547 | 2,186,534 | | | 2021 | 568,077 | 836,333 | 467,500 | — | — | — | 25,200 | 1,897,110 | | David A. Dykstra Vice Chairman and Chief Operating Officer | 2023 | 847,923 | 625,000 | 1,348,750 | — | — | — | 38,393 | 2,860,066 | | | 2022 | 829,000 | 800,000 | 1,025,000 | — | 395,887 | — | 48,168 | 3,098,055 | | | 2021 | 819,039 | 1,210,160 | 688,500 | — | — | — | 45,646 | 2,763,345 | | Richard B. Murphy Vice Chairman and Chief Lending Officer | 2023 | 647,923 | 480,000 | 1,023,750 | — | — | — | 33,580 | 2,185,253 | | | 2022 | 629,000 | 600,000 | 775,000 | — | 293,250 | — | 52,844 | 2,350,094 | | | 2021 | 619,039 | 884,285 | 518,500 | — | — | — | 39,025 | 2,060,849 | | David L. Stoehr Executive Vice President and Chief Financial Officer | 2023 | 537,923 | 355,974 | 777,400 | — | — | — | 29,209 | 1,700,506 | | | 2022 | 518,000 | 434,000 | 575,000 | — | 211,312 | — | 28,674 | 1,766,986 | | | 2021 | 499,519 | 643,813 | 371,250 | — | — | — | 29,237 | 1,543,819 | | Kathleen M. Boege Executive Vice President, General Counsel and Corporate Secretary | 2023 | 481,366 | 314,000 | 672,750 | — | — | — | 20,808 | 1,488,924 |

  50. 2023 Summary Compensation Table

    (1) The amounts shown in this column for 2023 consists of, for each of the NEOs, the annual cash bonus paid in 2024 with respect to 2023 performance. The amounts shown in this column for 2023 represent performance-based restricted stock unit and time-based restricted stock unit awards granted under the Company’s LTIP. These awards are valued based on the aggregate grant date fair value computed in accordance with Financial Accounting Standards Board Accounting Standards Codification Topic 718, Compensation — Stock Compensation (“FASB ASC Topic 718”) and, in the case of performance-based restricted stock units, are reported based on the probable achievement of the performance-based vesting conditions at the time of grant. The grant date fair value of the awards represents the average of the high and low sale prices of the Common Stock on the date of grant, as reported by Nasdaq, multiplied by the number of shares subject to the award at target level. Under the LTIP, if the highest achievement level is attained for the 2023 performance-based restricted stock unit awards, the maximum grant date fair value for the performance-based and time-based awards is as follows: Mr. Crane $3,575,000; Mr. Dykstra $1,753,375; Mr. Murphy $1,330,875; Mr. Stoehr $1,010,620; and Ms. Boege $874,575. See Note 18 to the Audited Financial Statements included in the Company’s Form 10-K for the fiscal year ended December 31, 2023 for a discussion of the relevant assumptions used in calculating these amounts. Amounts in this column include the value of all other compensation paid to or received by the NEOs in 2023. Please see the “All Other Compensation” table below for further information regarding these amounts. All Other Compensation for Mr. Wehmer includes the total of the monthly installments of the CEO Transition Award that were paid to Mr. Wehmer in 2023 pursuant to the Wehmer Agreement. Under the Wehmer Agreement (as defined above), Mr. Wehmer was awarded a one-time cash Transition Award of $12,000,000, payable in equal monthly installments over the 36-month period commencing on May 1, 2023 (subject to delayed payment to the extent required by tax law) and generally subject to Mr. Wehmer’s continued employment through each applicable payment date and his compliance with the restrictive covenants set forth in the Wehmer Agreement. See “2023 CEO Transition” on page 36. Perquisites are valued at actual amounts paid for such perquisites and other compensation. Private Aviation Usage was based on the total expense of private air travel based on the amount paid directly to the third-party vendor. Corporate Automobile Usage for Messrs. Wehmer, Dykstra and Murphy is calculated based on the IRS Annual Lease Value Table. Corporate Automobile Usage for Messrs. Crane and Stoehr and Ms. Boege is a cash automobile allowance. All Other Compensation

  51. 2023 Summary Compensation Table

    | Named Executive Officer | Private Aviation Usage ($) | Corporate Automobile Usage ($) | Club Memberships Not Exclusively For Business Use ($) | Life Insurance Premiums ($) | 401(k) Plan Matching Contribution ($) | CEO Transition Award | Total ($) | | Edward J. Wehmer | 30,000 | 6,482 | 20,866 | 14,159 | 5,000 | 2,333,333 | 2,409,840 | | Timothy S. Crane | — | 17,500 | 2,245 | 9,108 | 5,000 | — | 33,853 | | David A. Dykstra | — | 21,185 | — | 12,208 | 5,000 | — | 38,393 | | Richard B. Murphy | — | 8,016 | 8,038 | 12,526 | 5,000 | — | 33,580 | | David L. Stoehr | — | 12,000 | — | 12,209 | 5,000 | — | 29,209 | | Kathleen M. Boege | — | 12,000 | 2,518 | 1,290 | 5,000 | — | 20,808 |

  52. 2023 Summary Compensation Table

    * See Note 3 to the “2023 Summary Compensation Table” above.

  53. 2023 Grants of Plan-Based Awards Table

    2023 Grants of Plan-Based Awards Table

  54. 2023 Grants of Plan-Based Awards Table

    | | | Estimated Future Payouts Under Non-Equity Incentive Plan Awards | | | Estimated Future Payouts Under Equity Incentive Plan Awards(1) | | | All Other Stock Awards: Number of Shares of Stock or Units(2) (#) (i) | All Other Option Awards: Number of Securities Underlying Options (#) (j) | Exercise or Base Price of Option Awards ($/Sh) (k) | Grant Date Fair Value of Stock and Option Awards(3) ($/Sh) (l) | | Name (a) | Grant Date (b) | Threshold ($) (c) | Target ($) (d) | Maximum ($) (e) | Threshold (#) (f) | Target (#) (g) | Maximum (#) (h) | | | | | | Timothy S. Crane | 1/26/2023 | — | — | — | — | — | — | 12,248 | — | — | 1,100,000 | | | 1/26/2023 | — | — | — | 9,186 | 18,372 | 27,558 | — | — | — | 1,650,000 | | David A. Dykstra | 1/26/2023 | — | — | — | — | — | — | 6,007 | — | — | 539,500 | | | 1/26/2023 | — | — | — | 4,505 | 9,010 | 13,515 | — | — | — | 809,250 | | Richard B. Murphy | 1/26/2023 | — | — | — | — | — | — | 4,559 | — | — | 409,500 | | | 1/26/2023 | — | — | — | 3,419 | 6,838 | 10,257 | — | — | — | 614,250 | | David L. Stoehr | 1/26/2023 | — | — | — | — | — | — | 3,462 | — | — | 310,960 | | | 1/26/2023 | — | — | — | 2,596 | 5,192 | 7,788 | — | — | — | 466,440 | | Kathleen M. Boege | 1/26/2023 | — | — | — | — | — | — | 2,996 | — | — | 269,100 | | | 1/26/2023 | — | — | — | 2,247 | 4,494 | 6,741 | — | — | — | 403,650 |

  55. 2023 Grants of Plan-Based Awards Table

    The amounts in this column represent performance-based restricted stock unit awards granted to the NEOs pursuant to the 2023 LTIP and granted under the Wintrust Financial Corporation 2022 Stock Incentive Plan (the “2022 Plan”) that will be earned at the end of the performance period ending December 31, 2025 based on the Company’s achievement of performance objectives relating to the Company’s Adjusted EPS and Relative TSR. Subject to certain qualifying termination events, the participant is required to be employed on the award settlement date in order to vest in the award. (2) The amounts in this column represent time-based restricted stock unit awards granted to the NEOs pursuant to the 2023 LTIP and granted under the 2022 Plan that will be earned at the end of the vesting period ending January 26, 2026. Subject to certain qualifying termination events, the participant is required to be employed on the award settlement date in order to vest in the award. (3) The amounts in this column are valued based on the grant date fair value of the award calculated in accordance with FASB ASC Topic 718 based on the probable outcome of the applicable performance conditions. See Note 2 to the 2023 Summary Compensation Table for a discussion of the relevant assumptions used in calculating the grant date fair value. Narrative to the Summary Compensation Table and Grants of Plan-Based Awards Table As of December 31, 2023, each of our current NEOs was subject to an employment agreement with the Company. In the case of Messrs. Wehmer and Crane, their previous employment agreements were modified by the terms of their respective amended and restated employment agreements dated as of January 26, 2023, which were executed in connection with the transition of the CEO role from Mr. Wehmer to Mr. Crane, which occurred effective May 1, 2023, as discussed above. For Messrs. Dykstra and Murphy, the initial terms of their employment agreements expired in 2011 and the initial term of Mr. Stoehr’s employment agreement expired in 2009. The initial term of Ms. Boege’s employment agreement expired in 2016. However, each NEO’s agreement automatically renews for successive three-year terms, in the case of Messrs. Crane, Dykstra and Murphy, and one-year terms in the case of Mr. Stoehr and Ms. Boege, unless either the NEO or the Company provides notice of non-renewal at least 60 days prior to the expiration of the then-current term. For Mr. Wehmer, the initial term of the Wehmer Agreement ends on December 31, 2026, and the Wehmer Agreement is renewable beyond such initial term by the mutual written agreement of Mr. Wehmer and the Company not less than 90 days prior to expiration of the initial term (or any subsequent term). If a change in control occurs, the then-current term of each NEO’s employment agreement automatically extends for two years from the date of the change in control. If the term is extended due to a change in control, such extension will be further extended automatically for successive three-year terms, in the case of Messrs. Crane, Dykstra and Murphy, and one-year terms in the case of Mr. Stoehr and Ms. Boege, unless either the NEO or the Company provides notice of non-renewal at least 60 days prior to the expiration of the then-current term.

  56. 2023 Outstanding Equity Awards at Fiscal Year-End Table

    2023 Outstanding Equity Awards at Fiscal Year-End Table The following table sets forth information for each NEO with respect to each award of restricted stock units that has not vested and remained outstanding at December 31, 2023. The market value as of December 31, 2023 has been calculated using the closing price of the Company’s Common Stock on December 29, 2023 of $92.75, as reported on Nasdaq. As of December 31, 2023, none of our NEOs held any outstanding stock options.

  57. 2023 Outstanding Equity Awards at Fiscal Year-End Table

    | | Options Awards | | | | | Stock Awards | | | | | Name (a) | Number of Securities Underlying Unexercised Options (#) Exercisable (b) | Number of Securities Underlying Unexercised Options Unexercisable (#) (c) | Equity Incentive Plan Awards: Number of Securities Underlying Unexercised Unearned Options (#) (d) | Option Exercise Price ($) (e) | Option Expiration Date (f) | Number of Shares or Units of Stock That Have Not Vested (#) (g) | Market Value of Shares or Units of Stock That Have Not Vested ($) (h) | Equity Incentive Plan Awards: Number of Unearned Shares, Units or Other Rights that Have Not Vested (#)(1) (i) | Equity Incentive Plan Awards: Market or Payout Value of Unearned Shares, Units or Other Rights That Have Not Vested ($) (j) | | Edward J. Wehmer | — | — | — | — | — | 16,122(2) | 1,495,315 | — | — | | | — | — | — | — | — | 11,834(4) | 1,097,604 | 17,750(5) | 1,646,313 | | | — | — | — | — | — | 36,272(3) | 3,364,228 | — | — | | Timothy S. Crane | — | — | — | — | — | 2,979(2) | 276,302 | — | — | | | — | — | — | — | — | 2,979(4) | 271,665 | 4,392(5) | 407,358 | | | — | — | — | — | — | 12,248(6) | 1,136,002 | 18,372(7) | 1,704,003 | | | — | — | — | — | — | 6,702(3) | 621,611 | — | — | | David A. Dykstra | — | — | — | — | — | 4,387(2) | 406,894 | — | — | | | — | — | — | — | — | 4,213(4) | 390,756 | 6,320(5) | 586,180 | | | — | — | — | — | — | 6,007(6) | 557,149 | 9,010(7) | 835,678 | | | — | — | — | — | — | 9,870(3) | 915,443 | — | — | | Richard B. Murphy | — | — | — | — | — | 3,304(2) | 306,446 | — | — | | | — | — | — | — | — | 3,186(4) | 295,502 | 4,778(5) | 443,160 | | | — | — | — | — | — | 4,559(6) | 422,847 | 6,838(7) | 634,225 | | | — | — | — | — | — | 7,434(3) | 689,504 | — | — | | David L. Stoehr | — | — | — | — | — | 2,365(2) | 219,354 | — | — | | | — | — | — | — | — | 2,363(4) | 219,168 | 3,544(5) | 328,706 | | | — | — | — | — | — | 3,462(6) | 321,101 | 5,192(7) | 481,558 | | | — | — | — | — | — | 5,322(3) | 493,616 | — | — | | Kathleen M. Boege | — | — | — | — | — | 2,021(2) | 187,448 | — | — | | | — | — | — | — | — | 2,032(4) | 188,468 | 3,048(5) | 282,702 | | | — | — | — | — | — | 2,996(6) | 277,879 | 4,494(7) | 416,819 | | | — | — | — | — | — | 4,548(3) | 421,827 | — | — |

  58. 2023 Outstanding Equity Awards at Fiscal Year-End Table

    The amounts in this column represent restricted stock unit awards that remained subject to performance- based vesting conditions as of December 31, 2023. (2) Represents time-based restricted stock unit awards that vested on January 28, 2024. (3) Represents awards that vested and were settled on February 28, 2024, based on performance during the period from January 1, 2021 through December 31, 2023. The awards are reported at the actual vesting level, which was determined based on the Company’s achievement of Adjusted EPS and Relative TSR over the three-year performance period. (4) Represents time-based restricted stock unit awards that will vest on January 27, 2025. (5) Represents performance-based restricted stock unit awards that will be earned at the end of the January 1, 2022 through December 31, 2024 performance period based on the Company’s achievement of performance objectives relating to the Company’s Adjusted EPS and Relative TSR. These restricted stock unit awards are reported in this table assuming target achievement. Represents time-based restricted stock unit awards that will vest on January 26, 2026. Represents performance-based restricted stock unit awards that will be earned at the end of the January 1, 2023 through December 31, 2025 performance period based on the Company’s achievement of performance objectives relating to the Company’s Adjusted EPS and Relative TSR. These restricted stock unit awards are reported in this table assuming target achievement.

  59. 2023 Option Exercises and Stock Vested Table

    2023 Option Exercises and Stock Vested Table The following table sets forth information for each NEO with respect to the vesting of stock awards during 2023, and the value realized upon such vesting. No options were held or exercised by the NEOs during 2023.

  60. 2023 Option Exercises and Stock Vested Table

    | | Option Awards | | Stock Awards | | | Name (a) | Number of Shares Acquired on Exercise (#) (b) | Value Realized on Exercise ($) (c) | Number of Shares Acquired on Vesting (#)(1) (d) | Value Realized on Vesting ($)(2) (e) | | Edward J. Wehmer | — | — | 22,695 | 2,061,748 | | Timothy S. Crane | — | — | 3,736 | 339,400 | | David A. Dykstra | — | — | 6,176 | 561,064 | | Richard B. Murphy | — | — | 4,574 | 415,529 | | David L. Stoehr | — | — | 3,297 | 299,519 | | Kathleen M. Boege | — | — | 2,751 | 249,917 |

  61. 2023 Option Exercises and Stock Vested Table

    (1) Represents the vesting of performance-based stock awards granted under the Company’s 2015 Stock Incentive Plan. (2) The value realized on the vesting of performance-based stock awards represents the average of the high and low market price of the Common Stock on the date of vesting multiplied by the number of performance-based stock awards that vested.

  62. 2023 Nonqualified Deferred Compensation Table

    2023 Nonqualified Deferred Compensation Table

  63. 2023 Nonqualified Deferred Compensation Table

    | Name (a) | Executive Contributions in Last Fiscal Year ($) (b) | Registrant Contributions in Last Fiscal Year ($) (c) | Aggregate Earnings in Last Fiscal Year ($) (d) | Aggregate Withdrawals/ Distributions ($) (e) | Aggregate Balance at Last Fiscal Year End ($) (f) | | Edward J. Wehmer | — | — | 820,435(1) | 640,733(4) | 8,385,171(2) | | Timothy S. Crane | — | — | — | — | — | | David A. Dykstra | — | — | 405,362(1) | — | 3,783,114(3) | | Richard B. Murphy | — | — | — | — | — | | David L. Stoehr | — | — | — | — | — | | Kathleen M. Boege | — | — | — | — | — |

  64. 2023 Nonqualified Deferred Compensation Table

    (1) The amounts reported in the column entitled “Aggregate Earnings in Last Fiscal Year” represent the change in the value of the shares subject to the deferred LTIP and restricted stock unit awards from December 31, 2022 to December 31, 2023, net of distribution. (2) This amount represents the value of Mr. Wehmer’s deferred LTIP awards settled in 2017, 2018, and 2019 and his restricted stock unit awards which have vested but are not issuable until the earlier to occur of (i) the executive’s termination of employment and (ii) the time at which the award is no longer subject to the deduction limits under Section 162(m) of the Internal Revenue Code (the “Code”). (3) This amount represents the value of Mr. Dykstra’s restricted stock unit awards which have vested but are not issuable until the earlier to occur of (i) the executive’s termination of employment and (ii) the time at which the award is no longer subject to the deduction limits under Section 162(m) of the Code. This amount represents the value of Mr. Wehmer’s deferred LTIP awards settled in 2016 that were distributed in 2023 in accordance with the deferral terms of his LTIP award agreement.

  65. POTENTIAL PAYMENTS UPON TERMINATION OR CHANGE IN CONTROL

    POTENTIAL PAYMENTS UPON TERMINATION OR CHANGE IN CONTROL As noted under “Compensation Discussion & Analysis — Post-Termination Compensation” on page 51 of this Proxy Statement, we have entered into employment agreements with each of our NEOs that provide for payments in connection with such NEO’s termination, whether in connection with a change in control or otherwise. The benefits to be provided to the current NEOs under the employment agreements upon various termination situations are described below, including a summary of payments that would have been required had a termination taken place on December 31, 2023.

  66. CEO PAY RATIO DISCLOSURE

    CEO PAY RATIO DISCLOSURE As required by Section 953(b) of the Dodd-Frank Wall Street Reform and Consumer Protection Act, the Company is providing the following disclosure about the relationship of the annual total compensation of our employees to the annual total compensation of Mr. Crane, our President and Chief Executive Officer as of December 31, 2023. We believe that the pay ratio disclosed below is a reasonable estimate calculated in a manner consistent with Item 402(u) of Regulation S-K. For 2023, The median of the annual total compensation of all of our employees, other than Mr. Crane, was $77,286. • Mr. Crane’s annual total compensation, as reported in the Total column of the 2023 Summary Compensation Table, and as adjusted for annualization of his base salary for full year 2023, was $4,927,947. • Based on this information, the ratio of the annual total compensation of Mr. Crane to the median of the annual total compensation of all employees is estimated to be 63.8 to 1. We selected October 1, 2023 as the date on which to determine our median employee. As of that date, we had had approximately 5,433 employees. The pay ratio disclosure rules provide an exemption for companies to exclude non-U.S. employees from the median employee calculation if non-U.S. employees in a particular jurisdiction account for five percent (5%) or less of the Company’s total number of employees. We applied this de minimis exemption when identifying the median employee by excluding 143 employees in Canada and one employee in Puerto Rico. After taking into account the de minimis exemption, 5,289 employees in the United States and zero employees located outside of the United States were considered for identifying the median employee. For purposes of identifying the median employee from the employee population base, other than Mr. Crane, we considered W-2 gross taxable wages for calendar year 2023. In addition, we annualized compensation for employees who commenced employment with the Company after January 1, 2023 or who terminated prior to December 31, 2023. In determining the annual total compensation of the median employee, such employee’s compensation was calculated in accordance with Item 402(c)(2)(x) of Regulation S-K, as required pursuant to the SEC executive compensation disclosure rules. This calculation is the same calculation used to determine total compensation for purposes of the 2023 Summary Compensation Table with respect to each of the NEOs.

  67. PAY VERSUS PERFORMANCE

    PAY VERSUS PERFORMANCE As required by Section 953(b) of the Dodd-Frank Wall Street Reform and Consumer Protection Act, and Item 402(v) of Regulation S-K, the Company is providing the following information for “Compensation Actually Paid,” as calculated per SEC disclosure rules, and the Company’s financial performance against specific performance metrics for each of the last four completed calendar years. The table below summarizes “Compensation Actually Paid” to Mr. Wehmer, the Company’s former Principal Executive Officer (“PEO”), “Compensation Actually Paid” to Mr. Crane, the Company’s current PEO, and the average “Compensation Actually Paid” to our NEOs other than Mr. Wehmer and Mr. Crane. In determining the “Compensation Actually Paid,” we are required to make various adjustments to amounts that have been reported in the Summary Compensation Table in previous years as the valuations methods for this section differ from those required in the Summary Compensation Table, primarily as it relates to equity valuations. Under the Summary Compensation Table rules, equity awards are reflected as compensation in the year of grant based on the full grant date fair value, whereas equity awards are reported as “Compensation Actually Paid” during the vesting period and are impacted by changes in the Company’s stock price through the vesting date. Similar to the Summary Compensation Table, “Compensation Actually Paid” includes the value of equity awards as compensation prior to vesting and, thus, such compensation may never be realized by the NEOs if the underlying vesting conditions are not satisfied.

  68. PAY VERSUS PERFORMANCE

    | Year(1) | Summary Compensation Table Total PEO — Mr. Wehmer(2) ($) | Compensation Actually Paid to PEO — Mr. Wehmer(3) ($) | Summary Compensation Table Total PEO — Mr. Crane(2) ($) | Compensation Actually Paid to PEO — Mr. Crane(3) ($) | Average Summary Compensation Table Total for Non-PEO NEOs(2) ($) | Average Compensation Actually Paid to Non-PEO NEOs(3) ($) | Value of Initial Fixed $100 Investment Based On(4): | | Net Income ($ in millions) | Adjusted EPS(6) ($) | | | | | | | | | Wintrust TSR ($) | Peer Group TSR(5) ($) | | | | 2023 | 3,600,802 | 4,822,614 | 4,893,480 | 4,980,483 | 2,058,687 | 2,257,999 | 141.06 | 109.02 | 623 | 14.78 | | 2022 | 7,542,089 | 8,359,216 | | | 2,350,417 | 2,507,670 | 125.94 | 99.06 | 510 | 12.63 | | 2021 | 7,140,312 | 9,915,585 | | | 2,066,281 | 2,621,076 | 133.32 | 119.74 | 466 | 9.64 | | 2020 | 5,702,248 | 2,873,349 | | | 1,672,199 | 1,155,692 | 88.23 | 87.20 | 293 | 9.83 |

  69. PAY VERSUS PERFORMANCE

    Mr. Wehmer served as the Company’s sole PEO in years 2020-2022 and the Company’s other NEOs for years 2020-2022 are Messrs. Dykstra, Murphy, Crane and Stoehr. Mr. Wehmer and Mr. Crane each served as the Company’s PEO in 2023 for the time periods as report above, and the Company’s other NEOs for 2023 are Messrs. Dykstra, Murphy, Stoehr and Ms. Boege. (2) Amounts reported in this column represent (i) the total compensation reported in the Summary Compensation Table for the applicable years for Mr. Wehmer and Mr. Crane and (ii) the average of the total compensation reported in the Summary Compensation Table for the Company’s other NEOs for the applicable years, as described in (1) above. (3) SEC rules require certain adjustments be made to the Summary Compensation Table totals to determine “Compensation Actually Paid” as reported in the Pay-versus-Performance Table. “Compensation Actually Paid” does not necessarily represent cash and/or equity value transferred to the applicable NEO without restriction, but rather is a value calculated under applicable SEC rules. In general, “Compensation Actually Paid” is calculated as the total compensation reported in the Summary Compensation Table adjusted to include the fair market value of equity awards as of December 31 of the applicable year or, if earlier, the vesting date. The Company does not provide a defined benefit plan so no adjustment for pension benefits is included. The following table details these adjustments:

  70. PAY VERSUS PERFORMANCE

    | Year | Summary Compensation Table Total ($)(a) | (Minus) Grant Date Fair Value of Stock Awards Granted in Fiscal Year ($)(b) | Plus Fair Value at Fiscal Year-End of Outstanding and Unvested Stock Awards Granted in Fiscal Year ($)(c) | Plus/(Minus) Change in Fair Value of Outstanding and Unvested Stock Awards Granted in Prior Fiscal Years ($)(d) | Plus Fair Value at Vesting of Stock Awards Granted in Fiscal Year that Vested During Fiscal Year ($)(e) | Plus/(Minus) Change in Fair Value as of Vesting Date of Stock Awards Granted in Prior Years for which Applicable Vesting Conditions Were Satisfied During Fiscal Year ($)(f) | (Minus) Fair Value as of Prior Fiscal Year- End of Stock Awards Granted in Prior Fiscal Years that Failed to Meet Applicable Vesting Conditions During Fiscal Year ($)(g) | Equals Compensation Actually Paid ($) | | Mr. Wehmer (PEO) | | | | | | | | | | 2023 | 3,600,802 | — | — | 1,078,267 | — | 143,545 | — | 4,822,614 | | 2022 | 7,542,089 | (2,878,750) | 2,848,340 | 847,537 | — | — | — | 8,359,216 | | 2021 | 7,140,312 | (2,530,000) | 4,319,490 | 985,783 | — | — | — | 9,915,585 | | 2020 | 5,702,248 | (1,265,000) | — | (751,895) | — | — | (812,004) | 2,873,349 | | Mr. Crane (PEO) | | | | | | | | | | 2023 | 4,893,480 | (2,750,000) | 2,585,759 | 227,640 | — | 23,604 | — | 4,980,483 | | Other NEOs(h) | | | | | | | | | | 2023 | 2,058,687 | (955,663) | 898,474 | 229,985 | — | 26,516 | — | 2,257,999 | | 2022 | 2,350,417 | (771,875) | 763,616 | 165,512 | — | — | — | 2,507,670 | | 2021 | 2,066,281 | (511,438) | 873,110 | 193,123 | — | — | — | 2,621,076 | | 2020 | 1,672,199 | (247,813) | — | (130,396) | — | — | (138,298) | 1,155,692 |

  71. PAY VERSUS PERFORMANCE

    (a) Represents Total Compensation as reported in the Summary Compensation Table for the indicated fiscal year. With respect to the other NEOs, amounts shown represent averages. (b) Represents the grant date fair value of the stock awards granted during the indicated fiscal year, computed in accordance with the methodology used for financial reporting purposes. (c) Represents the fair value as of the indicated fiscal year-end of the outstanding and unvested stock awards granted during such fiscal year, computed in accordance with the methodology used for financial reporting purposes and, for awards subject to performance-based vesting conditions, based on the probable outcome of such performance-based vesting conditions as of the last day of the fiscal year. (d) Represents the change in fair value during the indicated fiscal year of each stock award that was granted in a prior fiscal year and that remained outstanding and unvested as of the last day of the indicated fiscal year, computed in accordance with the methodology used for financial reporting purposes and, for awards subject to performance-based vesting conditions, based on the probable outcome of such performance-based vesting conditions as of the last day of the fiscal year. (e) Represents the fair value at vesting of the stock awards that were granted and vested during the indicated fiscal year, computed in accordance with the methodology used for financial reporting purposes. (f) Represents the change in fair value, measured from the prior fiscal year-end to the vesting date, of each stock award that was granted in a prior fiscal year and which vested during the indicated fiscal year, computed in accordance with the methodology used for financial reporting purposes. (g) Represents the fair value as of the last day of the prior fiscal year of the stock awards that were granted in a prior fiscal year and which failed to meet the applicable vesting conditions in the indicated fiscal year, computed in accordance with the methodology used for financial reporting purposes. (h) See (1) above for the NEOs included in the average for the indicated fiscal year. (4) Pursuant to rules of the SEC, the comparison assumes $100 was invested on December 31, 2019. Historic stock price performance is not necessarily indicative of future stock price performance. (5) The Peer Group TSR utilizes the NASDAQ Global Select Market bank stock as the peer group index, which is the same industry index used in the Company’s Annual Report on Form 10-K. (6) As noted in the “CD&A,” for 2023, the Committee views Adjusted EPS as an important metric of Company performance. Fifty percent of the performance-based restricted stock units vest based on the Company’s three-year cumulative earnings per share as adjusted to exclude income taxes, acquisition-related charges, and the provision for credit losses with such amount being further reduced by actual net charge-offs of loans. Relationship Between Pay and Performance We believe the “Compensation Actually Paid” in each of the years reported above and over the four-year cumulative period are reflective of the Committee’s emphasis on “pay-for-performance” as the “Compensation Actually Paid” fluctuated year-over-year, primarily due to the result of our stock performance and our varying levels of achievement against pre-established performance goals under our short-term incentive awards and the LTIP. The following charts display the “Compensation Actually Paid” to the PEO and the average of the “Compensation Actually Paid” to the other NEOs as compared to the Company’s Adjusted EPS, Net Income and TSR over the three most recently completed years as well as the relationship between the Company’s TSR and the Peer Group TSR over such four-year period. Performance Measures Used to Link Company Performance and Compensation Actually Paid to the NEOs The following is a list of financial performance measures, which in our assessment represent the most important financial performance measures used by the Company to link compensation actually paid to the NEOs for 2023: • Adjusted EPS • Net Income TSR relative ranking within KRX Index