Trulieve Cannabis : AGM Proxy 2024

Table of Contents

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

(Amendment No. )

____________________

Filed by the Registrant x

Filed by a Party other than the Registrant o

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

TRULIEVE CANNABIS CORP.

(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):

• 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

TRULIEVE CANNABIS CORP.

NOTICE OF ANNUAL GENERAL AND SPECIAL MEETING OF SHAREHOLDERS

OF TRULIEVE CANNABIS CORP.

AND

PROXY STATEMENT

FOR ANNUAL GENERAL AND SPECIAL MEETING OF SHAREHOLDERS

TO BE HELD VIRTUALLY ON JUNE 12, 2024 (www.virtualshareholdermeeting.com/TCNNF2024)

This proxy statement is dated April 29, 2024, and is first being made available to shareholders on or about April 30, 2024.

Table of Contents

Trulieve Cannabis Corp.

6749 Ben Bostic Road

Quincy, Florida 32351

Notice of Annual General and Special Meeting of Shareholders (the "Notice")

The 2024 annual general and special meeting of shareholders (the "Meeting") of Trulieve Cannabis Corp., a British Columbia corporation (the

"Company"), will be a virtual meeting held on June 12, 2024 beginning at 10:00 a.m. (Eastern Time), at www.virtualshareholdermeeting.com/TCNNF2024.

The following matters will be considered at the Meeting:

1. To set the number of directors of the Company at seven (7);
2. To elect seven directors for the forthcoming year from the nominees proposed by board of directors of the Company (the "Board");
3. To conduct a non-binding advisory vote on the compensation of the Company's named executive officers;
4. To approve the amendment and restatement of the Company's 2021 Omnibus Incentive Plan;
5. To ratify the selection by the Audit Committee of the Board of WithumSmith+Brown, PC as auditors for the Company for the year ending December 31, 2024; and
6. To conduct any other business as may properly come before the Meeting or any adjournment(s) or postponements of the Meeting.

This Notice of Meeting is accompanied by the proxy statement and the accompanying form of proxy ("Proxy Instrument"). As permitted by applicable securities law, the Company is using notice-and-access to deliver the proxy statement to shareholders. This means that the proxy statement is being posted online to access, rather than being mailed out. Notice-and-access substantially reduces the Company's printing and mailing costs and is environmentally friendly as it reduces paper and energy consumption. On or about April 29, 2024, we expect to make available the proxy statement, the audited annual consolidated financial statements of the Company for the fiscal year ended December 31, 2023, together with the notes thereto, and the independent auditor's report thereon and the related management's discussion and analysis on the "Investors" section of the Company's website at investors.trulieve.com, SEDAR+ at www.sedarplus.comand the SEC's website at www.sec.gov. Shareholders will still receive a Proxy Instrument or a voting instruction form in the mail so they can vote their shares but, instead of receiving a paper copy of the proxy statement, they will receive a notice with information about how they can access the proxy statement electronically and how to request a paper copy.

The record date for the determination of shareholders of the Company entitled to receive notice of and to vote at the Meeting or any adjournment(s) or postponements of the Meeting is April 25, 2024 (the "Record Date"). Shareholders of the Company whose names have been entered in the register of shareholders of the Company at the close of business on the Record Date will be entitled to receive notice of and to vote at the Meeting or any adjournment(s) or postponements of the Meeting.

A shareholder of the Company may attend the Meeting live via webcast or may be represented by proxy. Registered shareholders of the Company who are unable to attend the Meeting or any adjournment(s) or postponements of the Meeting via the webcast are requested to date, sign and return the accompanying Proxy Instrument for use at the Meeting or any adjournment(s) or postponements of the Meeting.

To be effective, the enclosed Proxy Instrument must be returned to Broadridge ("Broadridge") by mail using the enclosed return envelope to Vote Processing, c/o Broadridge, 51 Mercedes Way, Edgewood, NY 11717. Alternatively, you may vote by Internet at www.proxyvote.comand clicking "Vote" or by calling 1-800-690-6903. All instructions are listed on the enclosed Proxy Instrument. Your proxy or voting instructions must be received in each case no later than 11:59 p.m. (Eastern Time) on June 11, 2024 or, if the Meeting is adjourned, at least 48 hours (excluding Saturdays, Sundays and statutory holidays in the Province of British Columbia) before the beginning of any adjournment(s) to the Meeting.

Whether or not you plan to attend the Meeting via live webcast, we encourage you to read this proxy statement and promptly vote your shares. For specific instructions on how to vote your shares, please refer to the section entitled "How You Can Vote" and to the instructions on your proxy or voting instruction card.

Table of Contents

DATED as of April 29, 2024

By Order of the Board of Directors

/s/ Eric Powers

Eric Powers

Chief Legal Officer and Corporate Secretary

IMPORTANT NOTICE REGARDING THE AVAILABILITY OF PROXY MATERIALS FOR THE ANNUAL GENERAL AND SPECIAL MEETING OF SHAREHOLDERS TO BE HELD ON JUNE 12, 2024.

The Notice of Annual General and Special Meeting and Proxy Statement are available online at the "Investors" section of our website at investors.trulieve.com. The 2023 Annual Report to Shareholders, which includes our Form 10-K for the year ended December 31, 2023, is also available online at the "Investors" section of our website at investors.trulieve.com.

YOUR VOTE IS IMPORTANT. PLEASE VOTE YOUR PROXY OVER THE INTERNET BY VISITING WWW.PROXYVOTE.COMOR BY TELEPHONE [phone] OR MARK, SIGN, DATE AND RETURN YOUR PROXY CARD BY MAIL WHETHER OR NOT YOU PLAN TO ATTEND THE ANNUAL GENERAL MEETING.

Table of Contents

PROXY STATEMENT FOR THE 2024 ANNUAL GENERAL AND SPECIAL MEETING OF SHAREHOLDERS TO BE HELD ON JUNE 12,

2024

This proxy statement contains information about the 2024 annual general and special meeting of shareholders (the "Meeting") of Trulieve Cannabis Corp., to be held via live webcast on June 12, 2024 beginning at 10:00 a.m. (Eastern Time), at www.virtualshareholdermeeting.com/TCNNF2024. The board of directors of Trulieve Cannabis Corp. (the "board of directors" or the "Board") is using this proxy statement to solicit proxies for use at the Meeting. Unless the context otherwise requires, references to "we," "us," "our," "Company" or "Trulieve" or similar terms refers to Trulieve Cannabis Corp. together with its wholly-owned subsidiaries. The mailing address of our principal executive offices is 6749 Ben Bostic Road, Quincy, Florida 32351.

All properly submitted proxies will be voted in accordance with the instructions contained in those proxies. If no instructions are specified, the proxies will be voted in accordance with the recommendation of our Board with respect to each of the matters set forth in the accompanying Notice of Meeting. You may revoke it at any time up to and including the last business day preceding the day of the Meeting by giving our Corporate Secretary written notice to that effect or at the Meeting by providing written notice to our Corporate Secretary to that effect.

We made this proxy statement and our Annual Report on Form 10-K for the fiscal year ended December 31, 2023 available to shareholders on April 29, 2024.

Important Notice Regarding the Availability of Proxy Materials for the Annual General and Special

Meeting of Shareholders to be Held on June 12, 2024:

This proxy statement and our Annual Report on Form 10-K for the fiscal year ended December 31, 2023

are available for viewing, printing and downloading at www.proxyvote.com.

A copy of our Annual Report on Form 10-K for the fiscal year ended December 31, 2023, as filed with the U.S. Securities and Exchange Commission (the "SEC") on February 29, 2024, except for exhibits, will be furnished without charge to any shareholder upon written request to our Corporate Secretary at [e-mail]. This proxy statement and our Annual Report on Form 10-K for the fiscal year ended December 31, 2023 are also available on the "Investors" section of our website at investors.trulieve.com, the SEC's website at www.sec.govand SEDAR+ at www.sedarplus.com.

Table of Contents
Table of Contents
GENERAL INFORMATION ABOUT THE ANNUAL GENERAL MEETING AND VOTING	1
Proxy Materials	1
Shareholder Proposals and Director Nominations	8
Description of the Company's Voting Securities	9
Notice-and-Access	9
Obtaining Additional Information	10
PROPOSALS 1 and 2-ELECTION OF DIRECTORS	11
Board Skills Matrix	11
SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS AND MANAGEMENT	18
CORPORATE GOVERNANCE	20
Board of Directors	20
Board Oversight of Enterprise Risk	22
Board Leadership	22
Corporate Governance Principles and Code of Ethics	23
Compensation and Human Resources Committee Interlocks and Insider Participation	23
EXECUTIVE OFFICERS	24
Biographical Information	24
Delinquent Section 16(a) Reports	47
COMPENSATION AND HUMAN RESOURCES COMMITTEE REPORT	48
PROPOSAL 3: NON-BINDING, ADVISORY VOTE TO APPROVE THE COMPENSATION OF THE COMPANY'S NAMED EXECUTIVE
OFFICERS	49
PROPOSAL 4: APPROVAL OF THE AMENDMENT AND RESTATEMENT OF THE COMPANY'S 2021 OMNIBUS INCENTIVE PLAN	50
PROPOSAL 5: APPOINTMENT OF AUDITORS	59
Change in Independent Registered Public Accounting Firm	59
Principal Independent Accountant Fees and Services	60
OTHER MATTERS	62
Availability of Form 10-K and Annual Report to Shareholders	62
Where to Find Additional Information	62
Cost of Proxy Solicitation	62
APPENDIX A - Predecessor Auditor Letter	A-1
APPENDIX B - Second Amended and Restated Trulieve Cannabis Corp. 2021 Omnibus Incentive Plan	B-1

i

Table of Contents

GENERAL INFORMATION ABOUT THE ANNUAL GENERAL AND SPECIAL MEETING AND VOTING

Proxy Materials

Why am I receiving these materials?

Our Board is using this proxy statement to solicit proxies for use at the Meeting to be held via live webcast on June 12, 2024 and is making these materials available by posting them online to access, rather than mailing them out unless requested by a shareholder. The cost of any solicitation will be borne by the Company. Proxies may also be solicited personally by employees of the Company at nominal cost to the Company.

As a shareholder, you are invited to attend the Meeting and are entitled and requested to vote on the business items described in this proxy statement. This proxy statement is furnished in connection with the solicitation of proxies by or on behalf of management of the Company and the Board. This proxy statement is designed to assist you in voting your shares and includes information that we are required to provide under the rules of the SEC and applicable Canadian securities laws.

These proxy materials are being sent to both registered and non-registered shareholders. In some instances, the Company has distributed copies of the Notice, the proxy statement and the accompanying Proxy Instrument (collectively, the "Documents") to clearing agencies, securities dealers, banks and trust companies, or their nominees (collectively "Intermediaries", and each an "Intermediary") for onward distribution to shareholders whose shares are held by or in the custody of those Intermediaries ("Non-registeredShareholders"). The Intermediaries are required to forward the Documents to Non- registered Shareholders.

Solicitation of proxies from Non-registered Shareholders will be carried out by Intermediaries, or by the Company if the names and addresses of Non- registered Shareholders are provided by the Intermediaries.

Non-registered Shareholders who have received the Documents from their Intermediary should follow the directions of their Intermediary with respect to the procedure to be followed for voting at the Meeting. Generally, Non-registered Shareholders will either:

• receive a form of proxy executed by the Intermediary but otherwise uncompleted. The Non-registered Shareholder may complete the proxy and return it directly to Broadridge; or
• be provided with a request for voting instructions. The Intermediary is required to send the Company an executed form of proxy completed in accordance with any voting instructions received by the Intermediary.

If you are a Non-registered Shareholder, and the Company or its agent has sent these materials directly to you, your name and address and information about your holdings of securities have been obtained from your Intermediary in accordance with applicable securities regulatory requirements. By choosing to send the Documents to you directly, the Company (and not your Intermediary) has assumed responsibility for: (i) delivering the Documents to you; and

1. executing your proper voting instructions. Non-registered Shareholders who have elected to receive the Documents by electronic delivery ("e- Delivery") will have received e-mail notification from the Intermediary that the Documents are available electronically on the Company's website. Please return your voting instructions as specified in the request for voting instructions.

Receiving Future Meeting Materials by Email

e-Delivery ensures that Shareholders receive documents faster, helps reduce printing and postage expenses and creates less paper waste. Shareholders who wish to enroll in e-Delivery may sign up at www.proxyvote.com.

What is included in the proxy materials?

The proxy materials include:

• our Notice of Meeting;
• our proxy statement for the Meeting;
• a Proxy Instrument or voting instruction card; and
• our Annual Report on Form 10-K for the fiscal year ended December 31, 2023.

1

Table of Contents

What information is contained in this proxy statement?

The information in this proxy statement relates to the proposals to be voted on at the Meeting, the voting process, our Board and board committees, corporate governance, the compensation of our directors and executive officers and other required information.

I share an address with another shareholder, and we received only one paper copy of the proxy materials. How may I obtain an additional copy?

If you share an address with another shareholder, you may receive only one set of proxy materials unless you have provided contrary instructions. If you wish to receive a separate set of the materials, please request the additional copy by contacting our Corporate Secretary at [e-mail] by calling us at [phone]. A separate set of the materials will be sent promptly following receipt of your request.

If you are a shareholder of record and wish to receive a separate set of proxy materials in the future, or if you have received multiple sets of proxy materials and would like to receive only one set in the future, please contact Broadridge Financial Solutions at:

Broadridge

51 Mercedes Way

Edgewood, NY 11717

1-866-540-7095

If you are a beneficial owner of shares and you wish to receive a separate set of proxy materials in the future, or if you have received multiple sets of proxy materials and would like to receive only one set in the future, please contact your bank or broker directly.

Shareholders also may write to, or email us, at the address below to request a separate copy of the proxy materials:

Trulieve Cannabis Corp.

Attn: Corporate Secretary

6749 Ben Bostic Road

Quincy, Florida 32351

[e-mail]

Who pays the cost of soliciting proxies for the Meeting?

We will bear the cost of solicitation. This solicitation of proxies is being made to shareholders by mail, but may be supplemented by telephone or other personal contact.

We will not reimburse brokerage houses and other custodians, nominees and fiduciaries for forwarding proxy materials to beneficial shareholders.

What items of business will be voted on at the Meeting?

The business items to be voted on at the Meeting are:

• To set the number of directors of the Company at seven (7);
• To elect seven directors for the forthcoming year from the nominees proposed by the Board;
• To conduct a non-binding advisory vote on the compensation of the Company's named executive officers;
• To approve the amendment and restatement of the Company's 2021 Omnibus Incentive Plan;
• To ratify the selection by the Audit Committee of the Board of WithumSmith + Brown, PC ("Withum"), as auditors for the Company for the year ending December 31, 2024; and
• To conduct any other business as may properly come before the Meeting or any adjournment(s) or postponements of the Meeting.

2

Table of Contents

How does the Board recommend that I vote?

The Board recommends that you vote:

• "FOR" setting the number of directors at seven (7);
• "FOR" each of its nominees for re-election to the Board until their respective successors are duly elected and qualified;
• "FOR" the approval, on a non-binding advisory basis, on the compensation of the Company's named executive officers;
• "FOR" the approval of the amendment and restatement of the Company's 2021 Omnibus Incentive Plan; and
• "FOR" the appointment of Withum, as auditors for the Company for the year ending December 31, 2024.

What vote is required to approve each item?

To conduct business at the Meeting, the quorum of shareholders is one person who is, or who represents by proxy, one or more shareholders who, in the aggregate, hold at least 5% of the issued shares entitled to be voted at the Meeting.

Proposals 1 and 2 - Election of Directors - The affirmative vote of a majority of the shares present or represented by proxy at the Meeting is required to set the number of directors of the Company at seven (7) and elect each director nominee. You may vote "FOR" or "AGAINST" the proposal to set the number of directors of the Company at seven (7). Broker non-votes will have no effect on the outcome of the proposal to set the number of directors at seven (7). You may vote "FOR" or "WITHHOLD" with respect to each of the director nominees. Withheld votes and broker non-votes will have no effect on the outcome of the election of the directors.

The Board has adopted a "majority voting" policy (the "Majority Voting Policy"). Pursuant to the Majority Voting Policy, at meetings of shareholders at which directors are to be elected, shareholders will vote in favor of, or withhold from voting for, each nominee separately. If, with respect to any particular nominee, the number of votes withheld exceeds the votes cast in favor of the nominee, then pursuant to the Majority Voting Policy the nominee shall be considered not to have received the support of the shareholders, even though duly elected as a matter of corporate law. An individual who is considered under the Majority Voting Policy not to have the support or confidence of the shareholders is expected forthwith to submit his or her resignation from the Board. Upon receiving such resignation, the nominating and corporate governance committee of our Board (the "Nominating and Corporate Governance Committee"), will consider it and make a recommendation to the Board on whether or not to accept the resignation.

In reviewing the Nominating and Corporate Governance Committee's recommendation, the Board shall consider the factors considered by the Nominating and Corporate Governance Committee and such additional factors as the Board considers relevant. The Board is expected to accept the recommendation of the Nominating and Corporate Governance Committee and to otherwise accept the resignation offer except in situations where exceptional circumstances would warrant the director continuing to serve on the Board. A director who has tendered a resignation pursuant to this policy will not participate in any deliberations of the Nominating and Corporate Governance Committee or the Board with respect to his or her resignation. The resignation will be effective when accepted by the Board. Within ninety (90) days of receiving a director's resignation, the Board will make a decision and issue a press release either announcing the resignation of the director or explaining why it has not been accepted. In determining whether or not to accept the resignation, the Board will take into account the factors considered by the Nominating and Corporate Governance Committee and any other factors the Board determines are relevant.

Proposal 3-Non-binding, Advisory Vote to Approve the Compensation of the Company's Named Executive Officers. The affirmative vote of a majority of the shares present or represented by proxy at the Meeting is required to approve this proposal. You may vote "FOR," "AGAINST" or "ABSTAIN" from voting on this proposal. Abstentions and broker non-voteswill have no effect on the outcome of the non-binding,advisory vote to approve the compensation of the Company's named executive officers.

Proposal 4-Approval of the amendment and restatement of the Company's 2021 Omnibus Incentive Plan. The affirmative vote of a majority of the shares present or represented by proxy at the Meeting is required to approve this proposal. You may vote "FOR," "AGAINST" or "ABSTAIN" from voting on this proposal. If you abstain from voting on this matter, your shares will not be counted as "votes cast" with respect to such matter, and the abstention will have no effect on the proposal. This proposal is considered to be a routine item, and your broker will be able to vote on this proposal even if it

3

Table of Contents

does not receive instructions from you. Accordingly, we do not anticipate that there will be any broker non-votes on this proposal; however, any broker non-votes will not be counted as "votes cast" and will therefore have no effect on the proposal.

Proposal 5-Approval of the Ratification of WithumSmith + Brown, PC as Independent Registered Public Accounting Firm. The affirmative vote of a majority of the shares present or represented by proxy at the Meeting is required to approve this proposal. You may vote "FOR," "AGAINST" or "ABSTAIN" from voting on this proposal. If you abstain from voting on this matter, your shares will not be counted as "votes cast" with respect to such matter, and the abstention will have no effect on the proposal. This proposal is considered to be a routine item, and your broker will be able to vote on this proposal even if it does not receive instructions from you. Accordingly, we do not anticipate that there will be any broker non-voteson this proposal; however, any broker non-voteswill not be counted as "votes cast" and will therefore have no effect on the proposal.

What happens if additional items are presented at the Meeting?

As of the date of this proxy statement, management of the Company knows of no such amendments, variations or other matters to come before the Meeting. However, if other matters properly come before the Meeting, it is the intention of the persons named in the enclosed Proxy Instrument to vote such proxy according to their best judgment.

Where can I find the voting results?

We expect to announce preliminary voting results at the Meeting and to publish final results in a current report on Form 8-K that we will file in the United States with the SEC and in a press release that we will file in Canada on SEDAR+ promptly following the Meeting. Both the Form 8-K and press release will also be available on the "Investors" section of our website at investors.trulieve.com.

How You Can Vote

What shares can I vote?

You are entitled to vote all shares owned by you on the Record Date, including (1) shares held directly in your name as the shareholder of record and (2) shares held for you as the beneficial owner through a bank, broker or other nominee. On April 25, 2024, there were 341 shareholders of record holding (i) 164,063,460 outstanding Subordinate Voting Shares, each of which is entitled to cast one (1) vote per Subordinate Voting Share; and (ii) 14 shareholders of record holding 232,263.86 outstanding Multiple Voting Shares, each of which is entitled to cast 100 votes per Multiple Voting Share.

REGISTERED SHAREHOLDERS HAVE THE RIGHT TO APPOINT A PERSON TO REPRESENT HIM, HER OR IT AT THE MEETING OTHER THAN THE PERSON(S) DESIGNATED IN THE PROXY INSTRUMENT either by striking out the names of the persons designated in the Proxy Instrument and by inserting the name of the person or company to be appointed in the space provided in the Proxy Instrument or by completing another proper form of proxy and, in either case, delivering the completed proxy to Broadridge by mail using the enclosed return envelope to Vote Processing, c/o Broadridge, 51 Mercedes Way, Edgewood, NY 11717. Alternatively, you may vote by Internet at www.proxyvote.comand clicking "Vote" or by calling 1-800-690-6903.

What is the difference between holding shares as a shareholder of record and as a beneficial owner?

Many of our shareholders hold their shares through a bank, broker or other nominee rather than having the shares registered directly in their own name. Summarized below are some distinctions between shares held of record and those owned beneficially.

Shareholder of Record

If your shares are registered directly in your name with our transfer agent, Odyssey Trust Company, you are the shareholder of record of the shares. As the shareholder of record, you have the right to grant a proxy to vote your shares to representatives from the Company or to another person, or to vote your shares electronically at the Meeting. You will receive a proxy card to use in voting your shares either by mail or email.

4