RumbleOn : 2023 Proxy Statement

UNITED STATES

SECURITIES AND EXCHANGECOMMISSION

WASHINGTON, D.C. 20549

___________________

SCHEDULE14A

___________________

Proxy Statement Pursuant to Section 14(a) of the

Securities Exchange Act of 1934

(Amendment No. __)

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

Check the appropriate box:

• Preliminary Proxy Statement
• Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2))

• Definitive Proxy Statement

• Definitive Additional Materials
• Soliciting Material under §240.14a-12

RumbleOn, Inc.

(Name of Registrant as Specified in its Charter)

_________________________________________________________________

(Name of Person(s) Filing Proxy Statement, if Other Than the Registrant)

Payment of Filing Fee (Check all boxes that apply):

• No fee required

• Fee paid previously with preliminary materials
• Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11

Table of Contents

RumbleOn, Inc.

901 W. Walnut Hill Lane, Suite 110A

Irving, Texas 75038

Dear Shareholders:

On behalf of the RumbleOn team, it is my pleasure to invite you to attend our 2024 Annual Meeting of Shareholders, which is scheduled to be held virtually on Tuesday, June 4, 2024, at 8:00 a.m. Central Time. In addition, I want to express my appreciation for your support and belief in RumbleOn's promising future. Having spent my entire career in the powersports industry, I am extremely excited to be leading this company. Today, I have even more conviction about our opportunity than when I joined just a few months ago.

Vision 2026:

On March 14, 2024, we introduced our three-year operating plan called Vision 2026, which is guided by our First Principle of creating and maximizing long-term per share value.

We expect the following to be achieved by calendar year 2026 while maintaining a healthy balance sheet1:·

• Annual revenue in excess of $1.7 billion;
• Annual Adjusted EBITDA2 of greater than $150 million; and
• Annual Adjusted Free Cash Flow3 of $90 million or more4.

We expect to achieve Vision 2026 and maintain a healthy balance sheet within our target leverage ratio of 1.5x-2.5xnet debt/EBITDA.

To achieve our Vision 2026 goals, the RumbleOn team will focus on the following three strategic pillars:

1. Leverage our national scale to run the best performing dealerships in America, supported by an aligned and efficient corporate office;
2. Grow our differentiated RideNow Cash Offer Technology to drive our pre-owned business; and
3. Effectively allocate the capital we create through operations, including strategic accretive acquisitions.

Below is additional detail on these important strategies:

Leveraging our national scale to run the best performing dealerships in America supported by an aligned and efficient corporate office. We will measure and define our dealership performance by using Net Profit and Customer Satisfaction metrics and have put several strategies in place to accomplish this. Strong manufacturer relationships are foundational to that success, as well as having an agile organization focused on the rider. This rider focused passion is what drives our culture.

____________

• See the important notice regarding forward-looking statements in the accompanying Proxy Statement.

• Adjusted EBITDA is a non-GAAP financial measure and should not be considered as an alternative to operating income or net income as a measure of operating performance. Non-GAAP financial measures are not necessarily calculated the same way by different companies and should not be considered a substitute for or superior to U.S. GAAP. We define Adjusted EBITDA as net income (loss) adjusted to add back interest expense, depreciation and amortization, the impact of income taxes, discontinued operations, non-cashstock-based compensation costs, the non-cash impairment of goodwill and franchise rights, transaction costs, certain litigation expenses not associated with our ongoing operations, and other non- recurring costs and credits, such as the gain on the sale of a dealership, insurance proceeds and costs attributable to an abandoned project, as such we do not consider such recoveries, charges and expenses to be a part of our core business operations, and they not necessarily an indicator of ongoing, future company performance.

• Adjusted Free Cash Flowis a non-GAAP financial measure and should not be considered as an alternative to cash flows or as

a measure of liquidity. Non-GAAP financial measures are not necessarily calculated the same way by different companies and should not be considered a substitute for or superior to U.S. GAAP. We define Adjusted Free Cash Flow as cash flows from operating activities of continuing operations less capital expenditures (excluding acquisitions).

• With respect to our 2026 Adjusted EBITDA and Adjusted Free Cash Flow targets, a reconciliation of these non-GAAP measures to the corresponding GAAP measures is not available without unreasonable effort due to the complexity of the reconciling items that we exclude from the non-GAAP measure or the variables going into the calculation of operating cash flows.

Table of Contents

Growing our RideNow Cash Offer Tool as a point of differentiation to drive the Pre-Owned business . The pre-ownedinventory market is a high-returnarea of growth for us and we are committed to intensifying our efforts on expanding this business. With the largest brick and mortar retail footprint in the country, we are aligning our store base with our Cash Offer operation to drive efficiencies in both the buying and retailing of pre-ownedproducts. In addition, we plan to pilot our first standalone, brick & mortar, pre-owneddealership in 2024, which will leverage our RideNow brand and a store operations team with more than 30 years of retail know-how.

Effectively allocate the capital we create through operations, including strategic accretive acquisitions. Our decisions around capital allocation will always be guided by our First Principle which is to create the greatest long-term per-sharevalue. We continually evaluate our dealership footprint and opportunities to strengthen it, whether by adding locations or exiting non-performingones. With 55% of our common stock held by our Board of Directors and the majority of my compensation directly tied to increasing our stock price, rest assured, we will think and act like true owners at every step of the way.

Our energy and focus will be our Vision 2026 plan and how we will shape the business to drive per share value over the coming years. It might take longer to get there based on macro or industry headwinds or key OEM product lifecycle timing; alternatively, we may get there earlier. But make no mistake, we will never take our eye off our First Principle at every stage of the journey; creating long-term per-sharevalue for our shareholders.

I want to acknowledge and thank key stakeholders for our Company. Our team of employees have done a lot of work over the last few months to develop our Vision 2026 plan and design the measures and activities to make it a reality. They continue to work hard in turning the company around. I also acknowledge the strong relationships with our manufacture partners who deliver great products and support programs to drive our mutual success at retail. Finally, I am grateful to our Board of Directors for their insights and advice and to you, our shareholders, for your confidence in our ability to create value in the coming years.

In closing, I hope you will participate in the Annual Meeting and ask for your support of our directors and the other items described in the accompanying Proxy Statement. Your participation is important, so please exercise your right to vote.

Sincerely,

Michael Kennedy

Chief Executive Officer

Table of Contents

RumbleOn, Inc.

901 W. Walnut Hill Lane, Suite 110A

Irving, Texas 75038

NOTICEOF THE2024 ANNUAL MEETING OF SHAREHOLDERS

You are cordially invited to attend the 2024 Annual Meeting of Shareholders of RumbleOn, Inc., a Nevada corporation (the "Company," "we," "us," or "our") on Tuesday, June 4, 2024 at 8:00 a.m. Central Time. The Annual Meeting will be held in a virtual format only, via a live webcast on the Internet, with no physical in- person meeting. You will be able to attend, participate, vote and submit questions at the Annual Meeting online by visiting www.virtualshareholdermeeting.com/RMBL2024 during the meeting.

We are holding the Annual Meeting for the following purposes, as more fully described in the accompanying Proxy Statement:

1. To elect seven directors, serving for a term until the 2025 Annual Meeting of Shareholders, or until their successors are duly elected and qualified, which we refer to as the "Director Election Proposal";
2. To obtain advisory approval of the Company's executive compensation ("Say on Pay"), which we refer to as the "Say on Pay Proposal";
3. To ratify the appointment of BDO USA, P.C. ("BDO") as our independent registered public accounting firm for the fiscal year ending December 31, 2024, which we refer to as the "Auditor Proposal"; and
4. To transact any other business that is properly presented at the Annual Meeting or any adjournments or postponements of the Annual Meeting.

The Board of Directors recommends that you vote FOR the election of all the director nominees, FOR the advisory approval of the Company's executive compensation (Say on Pay), and FOR the ratification of the appointment of BDO as our independent registered public accounting firm for the fiscal year ending December 31, 2024. Please refer to the accompanying Proxy Statement for detailed information on each of the proposals and the Annual Meeting.

The close of business on Monday, April 8, 2023 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. This notice of Annual Meeting, Proxy Statement, proxy card and copy of the Annual Report for the year ended December 31, 2023 are being distributed to shareholders on or about April 24, 2024.

Your vote at the Annual Meeting is important. 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.

By order of the Board of Directors:

Steven Pully

Chairman

RumbleOn, Inc.

IMPORTANT NOTICEREGARDING THEAVAILABILITYOF PROXYMATERIALS FOR THE

ANNUAL MEETING OF SHAREHOLDERS TO BEHELD ON JUNE4, 2024

The accompanying Proxy Statement and the 2023 Annual Report are available at

www.proxyvote.com

Table of Contents

TABLEOF CONTENTS

	Page
PROXYSTATEMENT	1
QUESTIONS AND ANSWERS ABOUT OUR ANNUAL MEETING	2
PROPOSAL 1: DIRECTOR ELECTION PROPOSAL	5
CORPORATE GOVERNANCE	8
EXECUTIVE COMPENSATION	12
PAYVERSUS PERFORMANCE	18
EXECUTIVE OFFICERS	21
SECURITYOWNERSHIP OF CERTAIN BENEFICIAL OWNERS AND MANAGEMENT	22
PROPOSAL 2: SAYON PAYPROPOSAL	24
REPORT OF THE AUDIT COMMITTEE	25
PROPOSAL 3: AUDITOR PROPOSAL	26
POLICYFOR APPROVAL OF AUDIT AND PERMITTED NON-AUDIT SERVICES	28
CERTAIN RELATIONSHIPS AND RELATED TRANSACTIONS	29
OTHER MATTERS	32

This Proxy Statement and the accompanying proxy materials (including the letter to shareholders and notice of annual meeting) may contain "forward-looking statements" as that term is defined under the Private Securities Litigation Reform Act of 1995, which statements may be identified by words such as "expects," "plans", "projects," "will," "may," "anticipates," "believes," "should," "intends," "estimates," and other words of similar meaning. Readers are cautioned not to place undue reliance on these forward-looking statements, which are based on our expectations as of the date of this Proxy Statement and speak only as of such date. Shareholders are advised to consider the factors listed under the heading "Forward-Looking Statements" and "Risk Factors" in the Company's Annual Report on Form 10-K and other filings made with the Securities and Exchange Commission, as such statements may be updated and amended from time to time, which factors may cause actual future events to differ materially from our expectations as of the date of this Proxy Statement. We undertake no obligation to publicly update or revise any forward-looking statements, whether as a result of new information, future events, or otherwise, except as required by law.

i

Table of Contents

PROXYSTATEMENT

This Proxy Statement contains information relating to the solicitation of proxies by the Board of Directors (the "Board") of RumbleOn, Inc. ("RumbleOn" or the "Company," or "we," "us," and "our") for use at our 2024 Annual Meeting of Shareholders (the "Annual Meeting"). Our Annual Meeting will be held in a virtual-only meeting format on Tuesday, June 4, 2024 at 8:00 a.m. Central Time. We believe that hosting a virtual Annual Meeting enables greater shareholder access, attendance and participation, improves meeting efficiency and provides a consistent experience to all shareholders regardless of location. We will provide a live webcast of the Annual Meeting at www.virtualshareholdermeeting.com/RMBL2024, where you will be able to submit questions and vote online. You will not be able to attend the meeting at a physical location.

The close of business on Monday, April 8, 2024 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. As of the Record Date, there were 50,000 shares of Class A common stock and 35,194,429 shares of Class B common stock issued and outstanding and entitled to vote at the Annual Meeting. This Proxy Statement and form of proxy are first being mailed to shareholders on or about April 24, 2024.

1

Table of Contents

QUESTIONS AND ANSWERS ABOUT OUR ANNUAL MEETING

What is the purpose of our Annual Meeting?

Our Annual Meeting will be held for the following purposes:

1. To elect seven directors, serving for a term until the 2025 Annual Meeting of Shareholders, or until their successors are duly elected and qualified, which we refer to as the "Director Election Proposal";
2. To obtain advisory approval of the Company's executive compensation ("Say on Pay"), which we refer to as the "Say on Pay Proposal";
3. To ratify the appointment of BDO as our independent registered public accounting firm for the fiscal year ending December 31, 2024, which we refer to as the "Auditor Proposal"; and
4. To transact any other business that is properly presented at the Annual Meeting or any adjournments or postponements of the Annual Meeting.

In addition, senior management will report on our business and respond to your questions of general interest regarding the Company.

Howcan I access the virtual Annual Meeting?

The live audio webcast of the Annual Meeting will begin promptly at 8:00 a.m. Central Time on June 4,

2024. To be admitted to the virtual Annual Meeting, you will need to log in at www.virtualshareholdermeeting.com/RMBL2024 using the 16-digit control number found on the proxy card previously mailed or made available to shareholders entitled to vote at the Annual Meeting. Because the Annual Meeting will be a completely virtual meeting, there will be no physical location for shareholders to attend.

Online access to the audio webcast will open 15 minutes prior to the start of the Annual Meeting to allow time for you to log in and test your device's audio system. The virtual Annual Meeting is running the most updated version of the applicable software and plugins. You should ensure you have a strong Internet connection wherever you intend to participate in the Annual Meeting. You should also allow plenty of time to log in and ensure that you can hear streaming audio prior to the start of the Annual Meeting.

Will I be able to ask questions and have these questions answered during the virtual Annual Meeting?

If you wish to submit a question, you may do so by logging into the virtual meeting platform at www.virtualshareholdermeeting.com/RMBL2024 using the 16-digitcontrol number found on the proxy card. Once you have logged in, you will need to type your question into the "Ask a Question" field and click "Submit." You may submit questions prior to or during the meeting. Appropriate questions related to the proposals being voted upon will be answered during the Annual Meeting, subject to time constraints. Additional information regarding the ability of shareholders to ask questions during the Annual Meeting, as well as rules of conduct and other materials for the Annual Meeting, will be available at www.virtualshareholdermeeting.com/RMBL2024.

What happens if there are technical difficulties during the Annual Meeting?

We will have technicians ready to assist you with any technical difficulties you may have accessing the virtual Annual Meeting, voting at the Annual Meeting or submitting questions at the Annual Meeting. If you encounter any difficulties accessing the virtual meeting during the check-in or meeting time, please call the technical support number that will be posted on the log in page at www.virtualshareholdermeeting.com/RMBL2024.

What are the voting rights of RumbleOn shareholders?

For each share of Class A common stock held at the Record Date, a shareholder is entitled to ten votes per share on each of the director nominees and ten votes per share on each other matter properly presented at the Annual Meeting.

2

Table of Contents

For each share of Class B common stock held at the Record Date, a shareholder is entitled to one vote per share on each of the director nominees and one vote per share on each other matter properly presented at the Annual Meeting.

What constitutes a quorum?

The presence in person or by proxy of the holders of one-third (33%) of the shares issued and outstanding and entitled to vote at the Annual Meeting constitutes a quorum with respect to all matters presented. If you submit a properly executed proxy or voting instruction card or properly cast your vote via the Internet, your shares will be considered part of the quorum even if you abstain from voting or withhold authority to vote as to a particular proposal. Pursuant to our Amended and Restated Bylaws, as amended (the "Amended and Restated Bylaws"), "broker non-votes" will be considered as present for purposes of determining whether a quorum exists.

What are "broker non-votes?"

"Broker non-votes" occur when shares held by a brokerage firm are not voted with respect to a proposal because the firm has not received voting instructions from the shareholder and the firm does not have the authority to vote the shares in its discretion. Under applicable rules, the Director Election Proposal and the Say on Pay Proposal are "non-routine" proposals and as such a broker does not have the discretion to vote on these proposals, if the broker has not received instructions from the beneficial owner of the shares. Brokers have the authority to vote on the Auditor Proposal if they have not received instructions from the beneficial owner of the shares.

Will my shares be voted if I do not provide my proxy?

If you are the "beneficial owner" of your shares, meaning that your shares are held by a brokerage firm, a bank, or through another holder of record and you do not provide the firm specific voting instructions, such firm will not have the authority to vote your shares for the Director Election Proposal or the Say on Pay Proposal, and your shares will not be voted and will be considered "broker non-votes," with respect to these proposals. We urge you to provide voting instructions so that your shares will be voted. If you hold your shares directly in your own name, your shares will not be voted unless you provide a proxy or vote before or during the virtual Annual Meeting.

Howdo I vote?

RumbleOn shareholders of record on April 4, 2024 have four ways to vote:

• By Internet at www.proxyvote.com until 11:59 p.m. Eastern Time on June 3, 2024 (have your 16-digit shareholder control number, which can be found on your proxy card, in hand when you access the website);
• By toll-free telephone at 1-800-690-6903 until 11:59 p.m. Eastern Time on June 3, 2024 (have your 16- digit shareholder control number, which can be found on your proxy card, in hand when you access the website);
• By mail, by marking, signing, and dating your proxy card and returning it in the postage- paid envelope provided to Vote Processing, c/o Broadridge, 51 Mercedes Way, Edgewood, NY11717; or
• Online during the Annual Meeting at www.virtualshareholdermeeting.com/RMBL2024 (have your 16-digitshareholder control number, which can be found on your proxy card, in hand when you vote online during the meeting).

Whether or not you plan to attend the meeting, we encourage you to vote by proxy as soon as possible. In order to be counted, proxies submitted by Internet or telephone must be received by 11:59 p.m. Eastern Time on June 3, 2024. Proxies submitted by U.S. mail must be received before the start of the Annual Meeting.

If your shares are registered in the name of broker, bank or other nominee (typically referred to as being held in "street name"), you will receive instructions from the holder of record. You must follow the instructions of the holder of record in order for your shares to be voted. Telephone and Internet voting will also be offered to shareholders owning shares through certain banks and brokers.

3

Table of Contents

Can I change my vote after I have voted?

You may revoke your proxy and change your vote at any time before the final vote at the Annual Meeting. You may change your vote via the Internet, by signing and mailing a new proxy card with a later date, or by participating in the virtual Annual Meeting and voting in person (only your latest proxy submitted prior to the Annual Meeting or our vote during the virtual Annual Meeting will be counted). However, your participation in the virtual Annual Meeting will not automatically revoke your proxy unless you vote at the virtual Annual Meeting or specifically request in writing that your prior proxy be revoked.

What vote is required to approve each proposal at the Annual Meeting?

Proposal 1 - Director Election Proposal.

In accordance with the Company's Amended and Restated Bylaws and Nevada law, the vote required to elect each director is a plurality vote. Withheld votes and broker non-votes will have no effect on the outcome of this proposal.

Proposal 2 - Say on Pay Proposal.

The vote required to approve the Say on Pay Proposal is a majority of the stock having voting power present in person or represented by proxy at the Annual Meeting. Abstentions and broker non-votes will have the same effect as a vote against this proposal.

Proposal 3 - Auditor Proposal.

The vote required to approve the Auditor Proposal is a majority of the stock having voting power present in person or represented by proxy at the Annual Meeting. Abstentions and broker non-votes will have the same effect as a vote against this proposal. Brokers have the authority to vote on the Auditor Proposal even if they have not received instructions from the beneficial owner of the shares.

Howdoes the Board recommend I vote on the proposals?

The Board recommends that you vote:

• FOR Proposal 1: the Director Election Proposal;
• FOR Proposal 2: the Say on Pay Proposal; and
• FOR Proposal 3: the Auditor Proposal.

Howwill the persons named as proxies vote?

If you complete and submit a proxy, the persons named as proxies will follow your voting instructions. If you submit and sign a proxy but do not provide instructions or if your instructions are unclear, the persons named as proxies will vote your shares in accordance with the recommendations of the Board, as set forth above.

With respect to any other proposal that properly comes before the Annual Meeting, the persons named as proxies will vote as recommended by our Board or, if no recommendation is given, in their own discretion.

Who will pay for the cost of soliciting proxies?

We will pay for the cost of soliciting proxies. RumbleOn will also reimburse brokers and other custodians, nominees and fiduciaries for their expenses in sending these materials to you and getting your voting instructions. In addition to the use of postal services or the Internet, proxies may be solicited by officers and employees of the Company (none of whom will receive any additional compensation for any assistance they may provide in the solicitation of proxies) in person or by telephone.

4

Table of Contents

PROPOSAL 1: DIRECTOR ELECTION PROPOSAL

On April 16, 2024, our Board approved an amendment to our Amended and Restated Bylaws that eliminated the previous classification of directors into Class I, Class II and Class II directors, with one class being elected each year to serve a staggered three-year term. As a result, our Board currently consists of seven members, all of whom serve for a term expiring at the 2024 Annual Meeting. Similarly, all directors elected at the 2024 Annual Meeting will serve for a one-year term, expiring at the 2025 Annual Meeting. Our Board is committed to sound corporate governance principles and practices and believes that shareholders should annually vote for the election of all directors.

Upon the recommendation of our Nominating and Corporate Governance Committee ("N&CGCommittee"), our Board has nominated the seven persons listed below to stand for election at the 2024 Annual Meeting and serve for a term until the 2025 Annual Meeting of Shareholders, or until their successors are duly elected and qualified. Each nominee listed below is willing and able to serve as a director of RumbleOn.

Below are the names of and certain information regarding our director nominees. All director nominees were previously nominated by the Company's N&CGCommittee and the full Board.

Name		Age		Position
Mark Cohen	42		Current Director/Director Nominee
William Coulter	68		Current Director/Director Nominee
Michael Kennedy	56		Current Director/Director Nominee
Rebecca Polak	53		Current Director/Director Nominee
Steven Pully	64		Current Director/Director Nominee
Michael Quartieri	55		Current Director/Director Nominee
Mark Tkach	67		Current Director/Director Nominee

DIRECTOR NOMINEES

Mark Cohen has served as a director of the Company since August 30, 2023. Mr. Cohen is the founder and managing partner of Stone House Capital Management, LLC ("Stone House"), a significant shareholder of the Company, and was appointed to the Board pursuant to the board nomination right granted to Stone House under the Standby Purchase Agreement, dated August 8, 2023, entered into by and among the Company, Stone House, Mark Tkach and William Coulter in connection with the rights offering completed by the Company in December 2023 (the "Rights Offering"). Mr. Cohen founded Stone House, a SEC registered investment advisor, in 2010. Prior to founding Stone House, he was an Investment Analyst at Force Capital Management,

LLC. Mr. Cohen holds a B.S. in Economics from the University of Pennsylvania's Wharton School.

We believe that Mr. Cohen possesses attributes that qualify him to serve as a member of the Board, including his investment experience in a wide range of public companies, which provides him with valuable insights and perspectives that can assist the Board.

William Coulter has served as a director of the Company since July 14, 2023. Previously, Mr. Coulter served as an executive officer and a director of RumbleOn and Executive Vice Chairman from August 2021 until February 2022 and as a Board observer from June 14, 2023 through July 14, 2023. Mr. Coulter currently serves as the Manager of Coulter Management Group LLLP, a business Mr. Coulter founded in 2011 to manage multiple auto dealerships and investments in real estate. Prior to joining the Company, Mr. Coulter served as a co-founder of RideNow with Mr. Tkach. He has significant experience in all aspects of powersports operations, including overseeing RideNow's financial and growth strategies from 1989 until it was acquired by the Company in August 2021. Under Mr. Coulter's leadership, RideNow grew from a single dealership into the largest powersports group of companies in the United States. Mr. Coulter has worked for auto dealerships for over

50 years and is an owner of several award-winning,Arizona-based auto dealerships.

We believe that Mr. Coulter possesses attributes that qualify him to serve as a member of our Board, including his extensive experience in the powersports and automotive sales industries.

Michael Kennedy has served as a director of the Company and as Chief Executive Officer since November 1, 2023. He previously served as the President and Chief Executive Officer of Vance & Hines, LLC from April 2019 until October 2023. Prior to that Mr. Kennedy served as Founder and Managing Partner of MWK Partner Advisors from December 2017 until March 2019. Mr. Kennedy is an accomplished powersports industry veteran with

5