Wintrust Financial : Download 2022 Proxy

WINTRUST FINANCIAL CORPORATION NOTICE OF ANNUAL MEETING OF SHAREHOLDERS

TO BE HELD ON MAY 26, 2022

To the Shareholders of Wintrust Financial Corporation:

You are cordially invited to attend the 2022 Annual Meeting of Shareholders (the "Annual Meeting") of Wintrust Financial Corporation (the "Company") to be held at our offices located at 9700 West Higgins Road, 2nd Floor, Rosemont, Illinois 60018 on Thursday, May 26, 2022, at 9:00 a.m. Central Time, for the following purposes:

• 1. To elect the 13 nominees for director named in this Proxy Statement to hold office until the 2023 Annual Meeting of Shareholders or until a successor has been elected and qualified;

• 2. To consider a proposal to approve the Company's 2022 Stock Incentive Plan;

• 3. To approve, on an advisory (non-binding) basis, the Company's executive compensation as described in this Proxy Statement;

• 4. To ratify the appointment of Ernst & Young LLP to serve as the independent registered public accounting firm for fiscal year 2022; and

• 5. To transact such other business as may properly come before the meeting and any adjournment thereof.

The record date for determining shareholders entitled to notice of, and to vote at, the Annual Meeting was the close of business on March 31, 2022. We encourage you to attend the Annual Meeting. Whether or not you plan to attend the Annual Meeting, prompt voting will be appreciated.

By order of the Board of Directors,

Kathleen M. Boege

Corporate Secretary

April 7, 2022

WHETHER OR NOT YOU PLAN TO ATTEND THE ANNUAL MEETING, IT IS IMPORTANT THAT YOU

VOTE BY ONE OF THE METHODS NOTED IN THE ATTACHED PROXY STATEMENT.

Important Notice Regarding the Availability of Proxy Materials for the Annual Meeting of Shareholders to be Held on May 26, 2022: This Notice of the Annual Meeting, Proxy Statement and the 2021 Annual Report on Form 10-K are

Available at:https://materials.proxyvote.com/97650W

TABLE OF CONTENTS

About the Meeting ........................................................................................................................................... Board of Directors, Committees and Governance ........................................................................................... Director Compensation .................................................................................................................................... Security Ownership of Certain Beneficial Owners, Directors and Management ............................................ Delinquent Section 16(a) Reports .................................................................................................................... Related Party Transactions ............................................................................................................................... Corporate Social Responsibility ....................................................................................................................... Proposal No. 1 - Election of Directors ........................................................................................................... Executive Officers of the Company ................................................................................................................. Executive Compensation - Compensation Discussion & Analysis ...............................................................

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2021 Summary Compensation Table .......................................................................................................

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2021 Grants of Plan-Based Awards Table ...............................................................................................

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2021 Outstanding Equity Awards at Fiscal Year-End Table ...................................................................

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2021 Option Exercises and Stock Vested Table .......................................................................................

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2021 Nonqualified Deferred Compensation Table ...................................................................................

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Potential Payments Upon Termination or Change in Control ......................................................................... CEO Pay Ratio Disclosure ............................................................................................................................... Compensation Committee Report .................................................................................................................... Proposal No. 2 - Approval of the 2022 Stock Incentive Plan ....................................................................... Equity Compensation Plan Information ........................................................................................................... Proposal No. 3 - Approval of, on an Advisory (Non-Binding) Basis, the Company's Executive Compensation as described in this Proxy Statement ....................................................................................... Report of the Audit Committee ........................................................................................................................ Proposal No. 4 - Ratification of Ernst & Young LLP to Serve as the Company's Independent

Registered Public Accounting Firm for Fiscal Year 2022 ............................................................................... Audit and Non-Audit Fees Paid ....................................................................................................................... Shareholder Proposals for the 2023 Annual Meeting ...................................................................................... Other Business ................................................................................................................................................. Annex A: 2022 Stock Incentive Plan .............................................................................................................

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WINTRUST FINANCIAL CORPORATION

9700 West Higgins Road, Suite 800

Rosemont, Illinois 60018

PROXY STATEMENT

FOR THE 2022 ANNUAL MEETING OF SHAREHOLDERS

TO BE HELD THURSDAY, MAY 26, 2022

These proxy materials are furnished in connection with the solicitation by the Board of Directors (the "Board" with individual members of the Board each being referred to herein as a "Director") of Wintrust Financial Corporation, an Illinois corporation ("Wintrust" or the "Company"), of proxies to be used at the 2022 Annual Meeting of Shareholders (the "Annual Meeting") and at any adjournment of such meeting. In accordance with rules and regulations of the Securities and Exchange Commission (the "SEC"), instead of mailing a printed copy of our proxy materials to each shareholder of record, we furnish proxy materials, which include this Proxy Statement (this "Proxy Statement") and the accompanying proxy card, Notice of Annual Meeting, and Annual Report on Form 10-K for fiscal year ended December 31, 2021, to our shareholders by making such materials available on the Internet unless otherwise instructed by the shareholder. If you received a Notice of Internet Availability of Proxy Materials (the "Notice") by mail and would like to receive a printed copy of our proxy materials, you should follow the instructions for requesting such materials included in the Notice, which is first being mailed to shareholders on or about April 14, 2022.

ABOUT THE MEETING

When and where is the Annual Meeting?

The Annual Meeting will be held on Thursday, May 26, 2022 at 9:00 a.m. Central Time at the Company's headquarters at 9700 West Higgins Road, 2nd Floor, Rosemont, Illinois 60018.

What is the purpose of the Annual Meeting?

At the Annual Meeting, shareholders will act upon the matters described in the Notice of Annual Meeting that accompanies this Proxy Statement, including the election of the 13 nominees for Director named in this Proxy Statement, a proposal to approve the Company's 2022 Stock Incentive Plan ("2022 Plan"), a proposal approving (on an advisory basis) the Company's executive compensation as described in this Proxy Statement, and the ratification of the Audit Committee's appointment of Ernst & Young LLP as the Company's independent registered public accounting firm for fiscal year 2022.

Who may vote at the Annual Meeting?

Only record holders of our Common Stock, no par value per share ("Common Stock"), as of the close of business on

March 31, 2022 (the "Record Date"), will be entitled to vote at the meeting. On the Record Date, the Company had outstanding approximately 57,253,214 shares of Common Stock. Each outstanding share of the Common Stock entitles the holder to one vote.

May shareholders ask questions at the Annual Meeting?

Yes. Shareholders will have the ability to submit questions during the Annual Meeting. Such questions must be confined to matters properly before the Annual Meeting and of general Company relevance.

What constitutes a quorum?

The Annual Meeting will be held only if a quorum is present. A quorum will be present if a majority of the shares of the

Common Stock issued and outstanding on the Record Date are represented, online or by proxy, at the Annual Meeting. Shares represented by properly completed proxy cards marked "abstain" or returned without voting instructions are counted as present for the purpose of determining whether a quorum is present at the Annual Meeting. Also, if shares are held by brokers who submit a proxy but are prohibited from exercising discretionary authority for beneficial owners who have not given voting instructions on certain matters ("broker non-votes"), those shares will be counted as present for the purpose of determining whether a quorum is present at the Annual Meeting.

How do I submit my vote?

If you are a shareholder of record, you can vote by:

• • attending the Annual Meeting and voting by ballot during the Annual Meeting;

• • using your telephone, according to the instructions on the Notice or proxy card;

• • visitingwww.voteproxy.comand then following the instructions on the screen; or

• • signing, dating and mailing in your proxy card which may be obtained by calling 888-proxyna (888-776-9962) or by [e-mail].

The deadline for voting by telephone or on the Internet is 11:59 p.m. Eastern Time on May 25, 2022. Proxy cards submitted by mail must be received by the close of business on May 25, 2022.

How do I vote if I hold my shares through a broker, bank or other nominee?

If you hold your shares through a broker, bank or other nominee, that institution will instruct you as to how your shares may be voted by proxy, including whether telephone or Internet voting options are available. If you hold your shares through a broker, bank or other nominee and would like to vote in person at the Annual Meeting, you must first obtain a valid legal proxy issued in your name from the institution that holds your shares and bring that proxy to the Annual Meeting.

Can I change or revoke my vote after I return my proxy card?

Yes. If you are a shareholder of record, you may change your vote by:

• • returning a later-dated proxy card;

• • entering a new vote by telephone or on the Internet (prior to 11:59 p.m. Eastern Time on May 25, 2022);

• • voting in person by ballot during the Annual Meeting; or

• • delivering written notice of revocation to the Company's Corporate Secretary by mail at 9700 West Higgins Road, Suite 800, Rosemont, Illinois 60018.

If you vote by phone or Internet, you may change your vote if you do so prior to 11:59 p.m. Eastern Time on May 25, 2022. Any later-dated proxy card or revocation sent by mail must be received by the close of business on May 25, 2022. If you hold your shares through an institution, that institution will instruct you as to how your vote may be changed.

Who will count the votes?

The Company's Inspector of Election, American Stock Transfer & Trust Company, LLC, will count the votes.

Will my vote be kept confidential?

Yes. As a matter of policy, shareholder proxies, ballots and tabulations that identify individual shareholders are kept secret and are available only to the Company, its tabulator and inspectors of election, who are required to acknowledge their obligation to keep your votes confidential.

Who pays to prepare, mail and solicit the proxies?

The Company pays all of the costs of preparing, mailing and soliciting proxies. The Company asks brokers, banks, voting trustees and other nominees and fiduciaries to forward proxy materials to the beneficial owners and to obtain authority to execute proxies. The Company will reimburse the brokers, banks, voting trustees and other nominees and fiduciaries upon request. In addition to solicitation by mail, telephone, facsimile, Internet or personal contact by its officers and employees, the Company has retained the services of Morrow Sodali LLC, 333 Ludlow Street, 5th Floor, South Tower, Stamford, Connecticut 06902, to solicit proxies for a fee of $7,000 plus expenses.

What are the Board's recommendations as to how I should vote on each proposal?

The Board recommends a vote:

• • FOR the election of each of the 13 Director nominees named in this Proxy Statement;

• • FOR the proposal to approve the Company's 2022 Stock Incentive Plan;

• • FOR the approval, on an advisory (non-binding) basis, of the Company's executive compensation as described in this Proxy Statement; and

• • FOR the ratification of the Audit Committee's appointment of Ernst & Young LLP as the Company's independent registered public accounting firm for fiscal year 2022.

How will my shares be voted if I sign, date and return my proxy card?

If you sign, date and return your proxy card and indicate how you would like your shares voted, your shares will be voted as you have instructed. If you sign, date and return your proxy card but do not indicate how you would like your shares voted, your proxy will be voted:

• • FOR the election of each of the 13 Director nominees named in this Proxy Statement;

• • FOR the proposal to approve the Company's 2022 Stock Incentive Plan;

• • FOR the approval, on an advisory (non-binding) basis, of the Company's executive compensation as described in this Proxy Statement; and

• • FOR the ratification of the Audit Committee's appointment of Ernst & Young LLP as the Company's independent registered public accounting firm for fiscal year 2022.

With respect to any other business that may properly come before the meeting, or any adjournment of the meeting, that is submitted to a vote of the shareholders, including whether or not to adjourn the meeting, your shares will be voted in accordance with the best judgment of the persons voting the proxies.

How will broker non-votes be treated?

A broker non-vote occurs when a broker who holds its customer's shares in street name submits proxies for such shares, but indicates that it does not have authority to vote on a particular matter. Generally, this occurs when brokers have not received any instructions from their customers. In these cases, the brokers, as the holders of record, are permitted to vote on "routine" matters only, but not on other matters. In this Proxy Statement, brokers who have not received instructions from their customers would only be permitted to vote on:

• • the ratification of the appointment of Ernst & Young LLP as the Company's independent registered public accounting firm for fiscal year 2022.

Brokers who have not received instructions from their customers would not be permitted to vote on the remaining proposals to be presented at the Annual Meeting, which are considered "non-routine" matters. Broker non-votes will have no impact on the voting results with regard to such proposals.

We will treat broker non-votes as present to determine whether or not we have a quorum at the Annual Meeting, but they will not be treated as entitled to vote on the "non-routine" matters described above, for which the broker indicates it does not have discretionary authority.

How will abstentions be treated?

For purposes of determining whether or not we have a quorum at the Annual Meeting, if you vote to abstain, your shares will be counted as present at the Annual Meeting.

If you abstain from voting for one or more of the nominees for Director, this will have the same effect as a vote against such nominee. If you abstain from voting on the proposal to approve the Company's 2022 Stock Incentive Plan, the advisory