Hagerty, Inc.

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 ☐Check the appropriate box:

(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 the appropriate box):

April 30, 2026

Dear Hagerty Stockholders,

We are pleased to invite you to attend the Annual Meeting of Stockholders of Hagerty, Inc. to be held on Tuesday, June 9,

2026, at 11:00 a.m. (ET). The Annual Meeting will be conducted virtually via live webcast, and you may participate by

attending online and voting your shares electronically.

Details regarding how to attend the meeting online, the business to be conducted at the meeting, and how to vote at the

meeting are more fully described in the accompanying Notice of the 2026 Annual Meeting of Stockholders and 2026 Proxy

Statement. On or about Thursday, April 30, 2026, we will mail a notice or proxy card to all stockholders entitled to vote at

the Annual Meeting containing instructions on how to access our proxy materials and vote. All of our proxy materials will be

available electronically. Stockholders who prefer a paper copy of the proxy materials may request this on or before May 26,

2026, by following the instructions provided in the notice we will send.

Your vote is important. Whether or not you plan to attend the Annual Meeting, we urge you to vote. You may vote by proxy

over the internet, by telephone, or by mail following the instructions on your notice or proxy card. Voting by proxy will

ensure your representation at the Annual Meeting regardless of whether you attend.

Onward and upward!

McKeel Hagerty

Chairman and CEO, Hagerty

Notice of the 2026 Annual Meeting

of Stockholders

The 2026 Annual Meeting of Stockholders (the "Annual Meeting") of Hagerty, Inc. ("we," "our," "us," “Hagerty,” or the

“Company”) will be held on Tuesday, June 9, 2026 at 11:00 a.m. (ET) and will be conducted virtually via live webcast. To

participate at this year’s Annual Meeting go to www.virtualshareholdermeeting.com/HGTY2026. You will be asked to

provide your 16-digit control number found on your notice or proxy card. You will be able to listen to the Annual Meeting

live and vote online. You will not be able to physically attend the Annual Meeting in person. We are holding the Annual

Meeting for the following purposes, as more fully described in the accompanying proxy statement:

Our Board of Directors has set April 10, 2026, as our record date for the Annual Meeting. Only stockholders that owned our

Class A Common Stock, Class V Common Stock, or Series A Convertible Preferred Stock ("Preferred Stock") at the close of

business on that day are entitled to notice and may vote at the Annual Meeting or any adjournment of the meeting. On or

about April 30, 2026, we expect to mail to our stockholders either a notice of internet availability of proxy materials (the

"Notice") or, if you elected to receive them by mail, a proxy card with a printed copy of our proxy materials (the "Proxy

Card"). The Notice provides instructions on how to vote and get our proxy materials electronically or have the proxy

materials mailed to you. The Proxy Card provides instructions on how to vote by telephone, mail, or the internet either

before or during the Annual Meeting. The proxy statement and our 2025 Annual Report on Form 10-K, filed with the

Securities and Exchange Commission (the "SEC") on February 26, 2026 (the "Annual Report") can be accessed directly on

our investor relations website at investor.hagerty.com, or at www.ProxyVote.com, where you will need your 16-digit control

number found on your Notice or Proxy Card to access the materials.

By Order of the Board of Directors,

Diana Chafey

Chief Legal Officer and Corporate Secretary

Table ofContents

Forward-Looking Statements

This proxy statement (the “Proxy Statement”) of Hagerty, Inc. ("we", "our", "us", "Hagerty", or the "Company") contains

statements that constitute "forward-looking statements" within the meaning of the Private Securities Litigation Reform Act of

1995. Forward-looking statements are statements about future events and expectations, and they involve risks and

uncertainties. All statements contained in this Proxy Statement other than statements of historical fact, are forward-looking

statements, including statements regarding our future operating results and financial position, our business strategy and

plans, products, services, and technology implementations, market conditions, growth and trends, expansion plans and

opportunities, and our objectives for future operations. Forward-looking statements can be identified by words such as

"anticipate," "believe," "envision," "estimate," "expect," "intend," "may," "plan," "predict," "project," "target," "potential," "will,"

"would," "could," "should," "continue," "ongoing," "contemplate," and other similar expressions, and the negative of these

expressions, although not all forward-looking statements contain these identifying words. Factors that could cause actual

results to differ materially from those expressed or implied in forward-looking statements include, among other things, our

ability to: compete effectively within our industry and attract and retain our insurance policyholders and paid Hagerty

Drivers Club subscribers; maintain key strategic relationships with our insurance distribution and underwriting carrier

partners; prevent, monitor, and detect fraudulent activity; manage risks associated with disruptions, interruptions, outages

or other issues with our technology platforms or our use of third-party services; accelerate the adoption of our membership

products as well as any new insurance programs and products we offer; successfully implement the new Markel fronting

arrangement and realize the anticipated benefits while also managing the increased exposure to underwriting volatility,

catastrophes, reinsurance counterparty risk, and legal, compliance and regulatory risks; underwrite and price new

products, including Enthusiast+, consistent with expected loss ratios and risk tolerances; execute Broad Arrow Group’s

private sale, auction, and financing strategies; manage the cyclical nature of the insurance business and broader

macroeconomic conditions, including inflation, interest rates, and potential recessionary pressures; achieve our investment

objectives and avoid losses in our investment portfolio; address unexpected increases in the frequency or severity of

claims catastrophe losses; and comply with the numerous laws and regulations applicable to our business, including state,

federal and foreign laws relating to insurance and rate increases, privacy and cybersecurity, marketing and advertising,

digital services, accounting matters, tax, artificial intelligence, anti-money laundering, economic sanctions, and the

internet. For a discussion of these and other factors that may affect our business, see the risk factors described under

"Item 1A. Risk Factors" in our Annual Report on Form 10-K for the fiscal year ended December 31, 2025 and in our

subsequent filings with the SEC.

You should not rely on forward-looking statements as predictions of future events. We operate in a very competitive and

rapidly changing environment and new risks emerge from time to time. The forward-looking statements in this Proxy

Statement represent our views as of the date hereof. We undertake no obligation to update any of these forward-looking

statements for any reason after the date of this Proxy Statement.