Company: CTLPP
Filing Date: 2025-07-24
Form Type: DEFM14A
Source: 0001140361-25-027048
Chunk: 11

Company: CANTALOUPE, INC.
Filing Date: 2025-07-24
Form: DEFM14A
Chunk 11
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, be canceled and retired and will cease to exist, and no consideration will be delivered in exchange for such cancellation and retirement. As of the date of this proxy statement, representatives of Douglas G. Bergeron, Chairman of the Board, and Jeffrey Dumbrell, Cantaloupe’s Chief Revenue Officer, have had preliminary discussions with representatives of 365 regarding potential rollover arrangements with respect to up to 1,032,559 shares of Cantaloupe’s common stock held by Mr. Bergeron and 20,000 shares of Cantaloupe’s common stock held by Mr. Dumbrell, but, as of the date of this proxy statement, no definitive agreement has been entered into between Mr. Bergeron or Mr. Dumbrell and 365 or its affiliates regarding such potential rollovers. Other than as described above, none of 365, Holdco, Holdco II, Merger Subsidiary or any of their respective affiliates has entered into any agreements, arrangements or understandings with respect to rollover shares. At or prior to the effective time of the Merger, 365 must deposit, or cause to be deposited, with the Paying Agent (as defined in the section of this proxy statement titled “ The Merger Agreement—Payment for Cantaloupe’s Common Stock”), for the benefit of the holders of common stock, cash in an amount sufficient to pay the merger consideration (which we refer to as the “Payment Fund”). For more information, see the sections of this proxy statement titled “ The Merger—Effects of the Merger” and “ The Merger—Interests of Certain Persons in the Merger—Employment Discussions; Rollover Agreements”. Effect on Preferred Stock Holders of preferred stock will not receive the merger consideration. Holders of preferred stock that convert their preferred stock into common stock will be entitled to receive the merger consideration for each share of common stock into which the preferred stock converts. Pursuant to the Merger Agreement, upon the terms and subject to the conditions set forth therein, Cantaloupe is required to redeem all of the outstanding shares of preferred stock immediately prior to the consummation of the Merger in accordance with the applicable redemption provisions contained in the Amended and Restated Articles of Incorporation of Cantaloupe (which we refer to as the “Cantaloupe Articles” and such redemption, the “Redemption”), at a redemption price payable in cash, by or on behalf of Cantaloupe, in an