Company: CTLPP
Filing Date: 2025-07-24
Form Type: DEFM14A
Source: 0001140361-25-027048
Chunk: 108

Company: CANTALOUPE, INC.
Filing Date: 2025-07-24
Form: DEFM14A
Chunk 108
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iii) incentive equity arrangements of 365 or its affiliates from and after the effective time of the Merger, including the allocation of any go-forward incentive equity “pool”.

In addition, at or prior to the effective time of the Merger, our directors and executive officers may enter into rollover agreements with 365, Holdco, Holdco II or Merger Subsidiary and contribute their shares of Cantaloupe stock to 365, Holdco, Holdco II or Merger Subsidiary, which shares of Cantaloupe stock will be subject to the treatment specified under the rollover agreement applicable to such rollover shares.

Following the execution of the Merger Agreement, representatives of 365 have had preliminary discussions with representatives of each of Douglas G. Bergeron, Chairman of the Board, and Jeffrey Dumbrell, Cantaloupe’s Chief Revenue Officer, regarding potential rollover arrangements with respect to shares of Cantaloupe’s common stock held by Mr. Bergeron or Mr. Dumbrell, as applicable, which shares are expected to be rollover shares for purposes of the Merger Agreement. As of July 21, 2025, the record date for the Special Meeting, Mr. Bergeron beneficially owned 1,152,559 shares of common stock and Mr. Dumbrell beneficially owned 609,142 shares of common stock, representing approximately 1.6% and 0.8%, respectively, of the voting power of the shares of Cantaloupe stock outstanding as of the record date and entitled to vote at the Special Meeting. Based on preliminary discussions held to date, 365 expects that, prior to the closing of the Merger, each of Mr. Bergeron and Mr. Dumbrell will enter into a rollover agreement with 365 or one of its affiliates 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, respectively. However, 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, and there can be no assurances that the terms of any such agreement will be agreed upon with Mr. Bergeron or Mr. Dumbrell. If Mr. Bergeron or Mr. Dumbrell and 365 or its