UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of the

Securities Exchange Act of 1934

Filed by the Registrant  ☒                             Filed by a Party other than the Registrant  ☐

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Stifel Financial Corp.

(Name of Registrant as Specified In Its Charter)

(Name of Person(s) Filing Proxy Statement, if other than the Registrant)

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LETTER FROM OUR CHAIRMAN & CEO

April 25, 20193, 2020

Fellow Shareholders:

We cordially invite you to attendparticipate in the 20192020 Annual Meeting of Shareholders of Stifel Financial Corp., which will be held onJune 5, 2019May 15, 2020 at 9:30 a.m., local time, at our corporate headquartersCentral Time, located at 501 North Broadway, St. Louis, Missouri 63102.. We hope that you will be able to attend.participate. We recognize that the current public health and travel situation may make it difficult for some of you make plans to attend anin-person meeting. For this reason,our meeting this year will be virtual-only, as detailed in the following proxy statement.

I thank John Dubinsky, who will retire from our Board of Directors on the date of our Annual Meeting, having served since 2003. We will not be losing John’s wisdom and experience: he will continue as chairman of Stifel Bank & Trust, which has prospered under his leadership.

Enclosed you will find a notice setting forth the business expected to come before the meeting and instructions for accessing this proxy statement and our Annual Report for the year ended December 31, 20182019 on the Internet and for submitting proxy votes online. The notice also contains instructions on how to request a printed set of proxy materials.

Your vote is very important to us. Whether or not you plan to attendparticipate in the virtual-only meeting in person,directly, we hope that your shares are represented and voted.

I expand on our Company’s performance, strategy, and outlook in the 2019 Annual Report Shareholder Letter, which I hope you will read.

Thank you for your investment in Stifel. I look forward to welcoming our shareholders to the Annual Meeting.

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TABLE OF CONTENTS

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NOTICE OF 20192020 ANNUAL MEETING OF SHAREHOLDERS

Important Notice Regarding the Availability of Proxy Materials for the Annual Meeting to be held on June 5, 2019:May 15, 2020:

Our proxy statement and 20182019 annual report are available at: www.investorvote.com/sf

By Order of the Board of Directors,

Mark P. Fisher, Corporate Secretary

April 25, 20193, 2020

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EXECUTIVE SUMMARY

This summary highlights certain information contained elsewhere in our Proxy Statement. You should read the entire Proxy Statement carefully before voting.

20192020 Annual Meeting Information

For additional information about our Annual Meeting, see theQuestions & Answers about the Annual Meeting and Voting, beginning on page 66.71.

Matters to be voted on at our 20192020 Annual Meeting

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PERFORMANCE HIGHLIGHTS

We encourage you to read the following Performance Highlights as background to this Proxy Statement.

*Announced

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$2.9bn

30  %

7,500

2,300

1,300

Low 7.7x leverage,(1) $3.2 billion shareholders’ equity and $2.9 billion market capitalization(2)

Insider ownership aligns employees’ interests with other shareholders (3)

Over 7,500 associates

Balanced business mix   ·      65% GWM     ·      35% IG   From 2018 net revenues

National presence with over 2,300 financial advisors

Largest U.S. equity research platform with approximately 1,300 stocks under coverage

Broad investment banking and institutional sales and trading capabilities – domestic and international

$4.1bn

29  %

8,000

2,200

1,300

Low 6.8x leverage,(1) $3.6 billion shareholders’ equity and $4.1 billion market capitalization(2)

Insider ownership aligns employees’ interests with other shareholders(3)

Over 8,000 associates

Balanced business mix   ·      64% GWM     ·      36% IG   From 2019 net revenues

National presence with over 2,200 financial advisors

Largest U.S. equity research platform with approximately 1,300 stocks under coverage

Broad investment banking and institutional sales and trading capabilities – domestic and international

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Notes:

Non-GAAP Net Revenues reflect operating results from continuing operations;

Excludes impact of sale of Sterne Agee Independent Contractor & Correspondent Clearing businesses;

Book Value Per Share adjusted for April 2011three-for-two stock split (2006-2010) and represents common equity per shares outstanding

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COMPENSATION HIGHLIGHTS

We provide highlights of our compensation program below. It is important that you review our CD&A, beginning on page 25, and summary compensation-related tables, beginning on page 54, in this Proxy Statement for an understanding of our compensation program.

This table summarizes our Compensation Committee’s compensation decisions for 20182019 for our Named Executive Officers.named executive officers. This table does not substitute for the Summary Compensation Table required by SEC rules. The compensation tables required by the SEC, including the Summary Compensation TablesTable, begin on page 54. 2018 was the first year for which Mr. Marischen was a named executive officer.

		Fixed Compensation				Annual Incentive Compensation, Variable						Subtotal		2018 Total
Named												At-Risk		Comp.
Executive				Stock-Based Salary
Officer   and Position		Base Salary				Cash Bonus		RSUs,           Debentures and RSAs(1)		PRSUs		Percent At-Risk		Change from 2017
Ronald J. Kruszewski		$200,000		$100,000		$4,020,761		$3,679,239		$1,000,000		$4,679,239		$9,000,000
Chairman and CEO												52.0%		12.5%
James M. Zemlyak		$250,000		$62,750		$1,895,065		$2,592,185		$500,000		$3,092,185		$5,300,000
Co-President and Head of Global Wealth Management												58.3%		12.5%
Victor J. Nesi		$250,000		$65,000		$2,785,000		$2,600,000		$500,000		$3,100,000		$6,200,000
Co-President and Director of the Institutional Group												50.0%		12.7%
Thomas B. Michaud		$250,000		$55,000		$2,775,000		$917,500		$207,500		$1,125,000		$4,205,000
President and CEO of Keefe, Bruyette & Woods												26.8%		2.3%
Thomas W. Weisel		$200,000		$70,000		$1,340,000		$260,000		$0		$260,000		$1,870,000
Senior Managing Director												13.9%		0%
James M. Marischen		$200,000		$135,000		$900,000		$300,000		$0		$300,000		$1,535,000
Chief Financial Officer												19.5%		n/a
		Realized Compensation						At-Risk Compensation

		Fixed Compensation				Annual Incentive Compensation, Variable						Subtotal		2019 Total
Named												At-Risk		Comp.
Executive				Stock-Based Salary
Officer   and Position		Base Salary, Cash				Cash Bonus		RSUs and Debentures		PRSUs		Percent At-Risk		Change from 2018
Ronald J. Kruszewski		$200,000		$100,000		$4,700,000		$3,250,000		$1,750,000		$5,000,000		$10,000,000
Chairman and CEO												50.0%		11.1%
James M. Zemlyak		$250,000		$62,750		$3,227,250		$1,610,000		$750,000		$2,360,000		$5,900,000
Co-President and Head of Global Wealth Management												40.0%		11.3%
Victor J. Nesi		$250,000		$65,000		$3,825,000		$1,890,000		$870,000		$2,760,000		$6,900,000
Co-President and Director of the Institutional Group												40.0%		11.3%
Thomas B. Michaud		$250,000		$55,000		$2,762,500		$1,062,500		$425,000		$1,487,500		$4,555,000
President and CEO of Keefe, Bruyette & Woods												32.7%		8.3%
James M. Marischen		$250,000		$125,000		$877,500		$337,500		$135,000		$472,500		$1,725,000
Chief Financial Officer												27.4%		12.4%
		Realized Compensation						At-Risk Compensation

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The Compensation Committee (the “Committee”) determined the pay of the named executive officers utilizing the Committee’s process for decision making and assessments as outlined beginning on page 34.32. The Committee took into consideration 2018 firm2019 Company performance as outlined beginning on page 36,35, individual named executive officer performance relative to their unique goals as well as their individual contribution to overall companyCompany achievements, leadership, and other factors, as outlined beginning on page 31,25, and, with respect to the compensation of the named executive officers other than the CEO, input from the CEO.

The Committee determined that, for 2018,2019, CEO compensation should be increased in line with performance, but with downward adjustments to moderate changes over multiple years.performance. This is consistent with the Committee’s past practices. Historically, CEO compensation has broadly tracked the performance of the three primary performance goals established by the Committee:non-GAAP Return on Equity,net revenue,non-GAAPpre-tax net income andnon-GAAP Earningsearnings per Share.share. In 2018,2019, for the year,non-GAAP Return on Equitynet revenue was up 3.1%10.3%,non-GAAPpre-tax net income was up 18.2%12.1% andnon-GAAP Earningsearnings per Shareshare were up 32.3%15.5%, or approximately 17.9%12.6% on average. The Committee also continued to recognize that the CEO’s existing shareholding,share ownership, which is significant, powerfully and directly aligns the CEO with the interests of all shareholders.

See “2018 Compensation“Compensation Determinations for Named Executive Officers Other than the CEO” on page 28 for a description of the Committee’s determinations for named executive officers other than the CEO. See “Use ofNon-GAAP Measures” on page 53 for a description of how and why these measures differ from GAAP measures.

Primary Performance Goal Results and CEO Compensation Relative to Primary Performance Goal Results

One-Year Relative Performance		Performance Over 5 Years Relative to 20132014

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SHAREHOLDERS’ SAY ON PAY: OUTREACH AND SHAREHOLDER INPUT

Last year, ourthe compensation program of Stifel Financial Corp. (referred to in this Proxy as Stifel or the Company) received support from 94%98% of shareholders voting. This is consistent with the strong support our pay decisions have received in recent years, and reflects the continuing commitment of senior management and the Committee to maintain a high level of shareholder outreach and respond more directly to shareholder input. We have continued to build on that strength. We believe that our outreach to shareholders concerning our executive compensation in recent years has enabled us both to obtain fuller shareholder input and also to communicate and to build on the enhancements we have made to the program. In addition to our ongoing dialogue with shareholders throughout the year, our outreach regarding our named executive officer compensation encompassed 16 of our top 20 institutional shareholders representing over 50% of outstanding shares. We also communicate regularly with our employees, who hold approximately 17%12% of outstanding shares. Our employees also hold restricted stock units that, if presently vested, would represent an additional 14%17% of outstanding shares, approximately. Our Committee has responded with commitment and action to shareholder feedback received through direct interactions and previous years’ “say on pay” advisory votes. These actions have included but are not limited to:to greater utilization of performance-based awards, clearly articulated goals, and fuller disclosure. In addition to implementing “Say“say on Pay”pay” feedback we have received from shareholders, we have also implemented additional feedback such as declassifying our Board, improving Board diversity and improving its diversity. Our Board also responded with a decision in 2017 to reduce the Board’s sizeindependence and increase its independence.focusing on environmental, social and governance fundamentals.

A number of our institutional shareholders publish proxy voting guidelines. Below are some typical guidelines on executive compensation, our corresponding response, and a cross reference to the section of this CD&A in which we provide additional information.

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CORPORATE GOVERNANCE HIGHLIGHTS

We strive to maintain a well-rounded and diverse Board that balances financial industry expertise with independence, and that balances the institutional knowledge of longer-tenured directors with the fresh perspectives brought by newer directors. As summarized below, our directors bring to our Board a variety of skills and experiences developed across a broad range of industries, both in established and growth markets, and in each of the public, private andnot-for-profit sectors.

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ITEM 1. ELECTION OF DIRECTORS

OUR DIRECTORS

Board of Director Nominees’ Qualifications and Experience

Our director nominees have a great diversity of experience and bring to our Board a wide variety of skills, qualifications and viewpoints that strengthen their ability to carry out their oversight role on behalf of shareholders.

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OUR DIRECTOR NOMINEES

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OUR CORPORATE GOVERNANCE PRINCIPLES

The Board has adopted Corporate Governance Guidelines (‘‘Principles’’), which are available in the corporate governance section of the Company’s web site at www.stifel.com. The Principles set forth the practices the Board follows with respect to, among other matters, the role and duties of the Board, size and composition of the Board, director responsibilities, Board committees, director access to officers, employees and independent advisors, director compensation and performance evaluation of the Board.

As described in the Principles, the role of the Board is to oversee management of the Company in its efforts to enhance shareholder value and conduct the Company’s business in accordance with its mission statement. In that connection, the Board helps management assess long-range strategies for the Company, and evaluates management performance.

It is a responsibility of the Board to regularly assess each director’s independence regularly and to take appropriate actions in any instance in which the requisite independence has been compromised. The Board has determined that Directors Berlew, K. Brown, M. Brown, Dubinsky, Grady, Ludeman, Markus, Oates, Peacock, and Zimmerman are independent directors under the rules of the NYSE and the SEC, including NYSE rules regarding the independence of the Compensation Committee, and reviewed information provided by the directors in questionnaires concerning the relationships that we may have with each director.

BOARD OF DIRECTORS – LEADERSHIP, RISK OVERSIGHT AND MEETINGS

Leadership: The continuing membership of our Board is composed of 89 independent directors and 2 employee directors.

The Board strategically considers the combination or separation of the Chairman and Chief Executive Officer roles as an integral part of its planning process and corporate governance philosophy. Ronald J. Kruszewski concurrently serves as both the Chairman of the Board and Chief Executive Officer. The Board believes that this structure serves the Company well because it provides consistent leadership and accountability for managing Company operations. However, our Board also holds regularly scheduled executive sessions without management, at which anon-managementthe lead independent director presides in compliance with the NYSE Corporate Governance Standards. These sessions occurred quarterly in 2018.2019.

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Lead Director: Mr. Grady has been elected by the Board to serve as the Independent Lead Director of Stifel Financial Corp. The Board has determined that the Lead Director will: have authority to call meetings of the independent directors; chair meetings of the independent directors; liaise between management and independent directors; serveex officioon all committees of which the lead director is not otherwise a member and, with the chair of the Compensation Committee, lead CEO performance evaluation and succession planning. The Board believes that the Lead Director role should be filled by an independent director selected by the independent directors in order to promote independence of oversight and development of the independent directors’ overall contribution to the Board.

Risk Oversight: Our Board has responsibility for the oversight of risk management. Our Board, either as a whole or through its Committees, regularly discusses with Company management our major risk exposures, their potential impact, and the steps we take to monitor and control such exposures.

While our Board is ultimately responsible for risk oversight, each of our Committees assists the full Board in fulfilling its oversight responsibilities in certain areas of risk. In particular, the Audit Committee focuses on the management of financial and accounting risk exposures. The Compensation Committee assists our Board in fulfilling its oversight responsibilities with respect to the management of risks arising from our compensation policies and programs. Finally, the Risk Management/Corporate Governance Committee focuses on the management of risks associated with Board organization, membership, and structure, and the organizational and governance structure of our Company,company, including cybersecurity matters.

We have an Enterprise Risk Management program under the direction of our Chief Risk Officer, who coordinates with five management committees: the Asset Liability Management Committee, the Products & Services Committee, the Conflicts of Interest Committee, the Operational Risk Committee, and the Disclosure Committee.

Meetings: During 2018,2019, our Board met 98 times, including both regularly scheduled and special meetings. During the year, attendance by the incumbent continuing directors of all meetings held by the Board and all Committees on which they serve exceeded 90%. It is the Company’s policy toWe encourage Board membersour directors to attend annual shareholders’ meetings.the Annual Meeting of Shareholders. Last year, two directors attended the Annual Meeting.

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BOARD OF DIRECTORS – COMMITTEES

The standing committees of our Board are the Audit Committee, Compensation Committee, Executive Committee, and Risk Management/Corporate Governance Committee. The Audit Committee, Compensation Committee, and Risk Management/Corporate Governance Committee each operates pursuant to a written charter approved by the Board. The full text of each such charter and our corporate governance guidelines are available in the “Corporate Governance” section of our web site located at www.stifel.com, or may be obtained by any shareholder, without charge, upon request by contacting Mark Fisher, our Corporate Secretary, at (415)364-2500 or bye-mail at investorrelations@stifel.com.

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OTHER GOVERNANCE MATTERS

Director Nominations by Shareholders

In accordance with the Risk Management/Corporate Governance Committee’s charter and our corporate governance guidelines, the Risk Management/Corporate Governance Committee considers nominees recommended by shareholders and reviews the qualifications and contributions of the directors standing for election each year.

Shareholders may recommend individuals to the Risk Management/Corporate Governance Committee for consideration as potential director nominees by giving written notice to Mark Fisher, our Corporate Secretary, at least 90 days, but not more than 120 days, prior to the anniversary of our preceding year’s annual meeting, along with the specific information required by ourBy-Laws, including, but not limited to, the name and address of the nominee; the number of shares of our common stock beneficially owned by the shareholder (including associated persons) nominating such nominee; and a consent by the nominee to serve as a director, if elected, that would be required for a nominee under the SEC rules. If you would like to receive a copy of the provisions of ourBy-Laws setting forth all of these requirements, please send a written request to Stifel Financial Corp., Attention: Mark P. Fisher, Corporate Secretary, One Financial Plaza, 501 North Broadway, St. Louis, Missouri 63102-2102. The Risk Management/Corporate Governance Committee has not adopted any specific procedures for considering the recommendation of director nominees by shareholders, but will consider shareholder nominees on the same basis as other nominees. Please also see the procedures described in the section entitled “How“How can I make a Shareholder Proposal for the 20202021 Annual Meeting?” on page 6873 of this Proxy Statement.

Code of Ethics and Corporate Governance

In accordance with the requirements of the NYSE and the Sarbanes-Oxley Act of 2002, we have adopted Corporate Governance Guidelines as well as charters for the Audit Committee, Compensation Committee, and Risk Management/Corporate Governance Committee. These guidelines and charters are available for review under the “Corporate Governance” section of our web site at www.stifel.com. We have also adopted a Code of Ethics for Directors, Officers, and Associates. The Code of Ethics is also posted in the “Corporate Governance” section of our web site, located at www.stifel.com, or may be obtained by any shareholder, without charge, upon request by contacting Mark P. Fisher, our Corporate Secretary, at (415)364-2500 or bye-mail at investorrelations@stifel.com.

We have established procedures for shareholders or other interested parties to communicate directly with our Board, including the presiding director at the executive sessions of thenon-management directors or thenon-management directors as a group. Such parties can contact our Board by mail at: Stifel Financial Corp., Attention: Ronald J. Kruszewski Chairman of the Board, One Financial Plaza, 501 North Broadway, St. Louis, Missouri 63102-2102. All communications made by this means will be received by the Chairmen of the Board and relayed promptly to the Board or the individual directors, as appropriate.

Relationship of Risk Management to Compensation

The Board and the Compensation Committee, with the assistance of management, has evaluated our compensation policies and practices for all employees and has concluded that such policies and practices do not create risks that are reasonably likely to have a material adverse effect on the Company. In reaching this conclusion, we undertook the following process:

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In light of the above, our Board and Compensation Committee continue to conclude that our compensation policies in general, and our incentive programs in particular, remain well aligned with the interests of our shareholders and do not create risks that are reasonably likely to result in a material adverse impact on the Company.

Age – Retirement of Mr. Dubinsky and Reduction in Board Size

The Board has adopted a policy, on the recommendation of its Executive Committee, that each Director, shall not stand for reelection in any year if he or she shall have reached the age of 75 as of the first day of that year and shall transition responsibilities and resign no later than the date of the annual meeting.Annual Meeting. The Board may make exceptions to this policy if it determines such exception would be in the firm’sCompany’s best interest. Accordingly, Mr. Dubinsky will not stand for election this year and his service on Stifel Financial’s Board will conclude concurrent with the end of this year’s Annual Meeting. Mr. Dubinsky will, however, remain chairman of the board of Stifel Bank & Trust, a subsidiary of the Company. The Board has determined into reduce the desire for an orderly transition,size of the Board from 12 to 11 directors concurrently with Mr. Dubinsky’s retirement. The Board has determined that Mr. Weisel and Mr. Dubinsky should continue to serve for the2019-202020-21 term.

Declassification of the Board

In 2016, shareholders approved the Board’s proposal to declassify the Board. No classified Board terms will continue beyond the 2019 Annual Meeting of Shareholders. Accordingly, if elected, each of the members presently nominated will be elected to unclassifiedone-year terms.

Experience and Diversity

The Risk Management/Corporate Governance Committee of the Board actively seeks directors who provide the Board with a diversity of perspectives and backgrounds.

The composition of our Board reflects diversity in business and professional experience, skills, gender and ethnic background.

When consideringThe Board and Risk Management/Corporate Governance Committee regularly consider whether directors and nominees have the experience, qualifications, attributes, and skills, taken as a whole, to enable the Board to satisfy its oversight responsibilities effectively in light ofeffectively. To do so the Company’s businessBoard and structure, the Risk Management/Corporate Governance Committee and the Board focusedfocus primarily on the information discussed in each of the individual biographies set forth in this section.section, and consider how this information relates to the Company’s business and structure. These biographies briefly describe the business experience during the past five years or(or longer if material,material), of each of the nominees for election as a director, and our other directors whose terms of office will continue after the Annual Meeting, including, where applicable, positions held with us, or our principal subsidiary, Stifel, Nicolaus & Company, Incorporated, and information as to the other directorships held by each of them during such five-year period. These biographies also include the specific individual attributes considered by the Risk Management/Corporate Governance Committee and the Board in coming to the conclusion that each such nominee or current director should serve as a director of the Company.

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COMPENSATION DISCUSSION & ANALYSIS

2018 CEO COMPENSATION DETERMINATIONS

In determining Mr. Kruszewski’s variable compensation for 2018,2019, the Committee specifically noted that:

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