RumbleOn, Inc.

901 W. Walnut Hill Lane

Irving, Texas 75038

October 20, 2021

Dear Fellow RumbleOn Stockholder:

We are pleased to invite you to join us at the 2021 Annual Meeting of Stockholders of RumbleOn, Inc. ("RumbleOn") to be held on Thursday, November 18, 2021 at 8:00 a.m. Central Time, at our offices in Texas at 901 W. Walnut Hill Lane, Irving, Texas 75038, Conference Room A.

The accompanying Notice of Annual Meeting and Proxy Statement describes the specific matters to be voted upon at the Annual Meeting. We also will report on our business and provide an opportunity for you to ask questions of general interest.

Whether you own a few or many shares of RumbleOn stock and whether or not you plan to attend the Annual Meeting in person, it is important that your shares be represented at the Annual Meeting. Your vote is important and we ask that you please cast your vote as soon as possible.

The Board of Directors recommends that you vote FOR the election of all the director nominees and FOR the advisory approval of the Company's executive compensation (Say on Pay). Please refer to the accompanying Proxy Statement for detailed information on each of the proposals and the Annual Meeting.

Sincerely,

Marshall Chesrown

Chairman and Chief Executive Officer

RumbleOn, Inc.

RumbleOn, Inc.

901 W. Walnut Hill Lane

Irving, Texas 75038

NOTICE OF THE 2021 ANNUAL MEETING OF STOCKHOLDERS

To Stockholders of RumbleOn, Inc.:

The 2021 Annual Meeting of Stockholders of RumbleOn, Inc. will be held on Thursday, November 18, 2021 at 8:00 a.m. Central Time, at our offices in Texas at 901 W. Walnut Hill Lane, Irving, Texas 75038, Conference Room A for the following purposes, as more fully described in the accompanying proxy statement:

  1. To elect nine directors, with the directors elected to Class I serving for a term until the 2022 Annual Meeting of Stockholders, the directors elected to Class II serving for a term until the 2023 Annual Meeting of Stockholders, and the directors elected to Class III serving for a term until the 2024 Annual Meeting of Stockholders, or until their successors are duly elected and qualified, which we refer to as "Director Election Proposal";
  2. To obtain advisory approval of the Company's executive compensation ("Say on Pay"), which we refer to as "Say on Pay Proposal"; and
  3. To transact any other business that is properly presented at the Annual Meeting or any adjournments or postponements of the Annual Meeting.

The close of business on October 8, 2021 has been fixed as the record date for the Annual Meeting (the "Record Date"). Only holders of record of RumbleOn Class A and Class B common stock on the Record Date are entitled to notice of, and to vote at the Annual Meeting or any adjournments or postponements of the Annual Meeting.

We cordially invite you to attend the Annual Meeting in person. Even if you plan to attend the Annual Meeting, we ask that you please cast your vote as soon as possible. As more fully described in the accompanying proxy statement, you may revoke your proxy and reclaim your right to vote at any time prior to its use.

Sincerely,

Thomas Aucamp

Chief Administrative Officer

and Corporate Secretary

IMPORTANT NOTICE REGARDING THE AVAILABILITY OF PROXY MATERIALS FOR THE

ANNUAL MEETING OF STOCKHOLDERS TO BE HELD ON NOVEMBER 18, 2021

The accompanying proxy statement and the 2020 Annual Report on Form 10-K are available at

http://www.rumbleon.com

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PROXY STATEMENT

TABLE OF CONTENTS

Page

PROXY STATEMENT � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � �

1

QUESTIONS AND ANSWERS ABOUT OUR ANNUAL MEETING� � � � � � � � � � � � � � � � � � � � � � � � � � � � � �

1

PROPOSAL 1: DIRECTOR ELECTION PROPOSAL � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � �

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CORPORATE GOVERNANCE � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � �

7

EXECUTIVE COMPENSATION � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � �

10

SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS AND MANAGEMENT � � � � � � � � � � �

15

PROPOSAL 2: SAY ON PAY PROPOSAL � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � �

17

REPORT OF THE AUDIT COMMITTEE� � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � �

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AUDITORS FEES AND SERVICES � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � �

19

POLICY FOR APPROVAL OF AUDIT AND PERMITTED NON-AUDIT SERVICES � � � � � � � � � � � � � � � �

20

CERTAIN RELATIONSHIPS AND RELATED TRANSACTIONS � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � �

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OTHER MATTERS � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � � �

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RumbleON Inc. published this content on 18 November 2021 and is solely responsible for the information contained therein. Distributed by Public, unedited and unaltered, on 17 November 2021 00:06:03 UTC.