Company: CTLPP
Filing Date: 2025-07-11
Form Type: PREM14A
Source: 0001140361-25-025663
Chunk: 20

Company: CANTALOUPE, INC.
Filing Date: 2025-07-11
Form: PREM14A
Chunk 20
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 employment agreements and pursuant to the Merger Agreement. |

| • | Certain of our executive officers have received Transaction Bonuses (as defined in the section of this proxy statement titled “The Merger—Interests of Certain Persons in the Merger—Transaction Bonuses”) that will be repayable to Cantaloupe if the closing of the Merger does not occur. |

| • | 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. As of the date of this proxy statement, Douglas G. Bergeron, Chairman of the Board, has had preliminary discussions with representatives of 365 regarding a potential rollover arrangement with respect to shares of Cantaloupe’s common stock held by Mr. Bergeron, but, as of the date of this proxy statement, there is no understanding as to the amount of shares of Cantaloupe’s common stock that would be subject to such rollover arrangement, and no definitive agreement has been entered into between Mr. Bergeron and 365 or its affiliates regarding such potential rollover. 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. |

| • | Prior to the effective time of the Merger, certain of our executive officers may enter into new employment arrangements with 365 that would become effective upon the closing of the Merger. As of the date of this proxy statement, none of our executive officers have entered into any arrangements with 365 with respect to their employment. |

Our Board was aware of these interests and considered them when it adopted the Merger Agreement and approved the Merger. For more information on the interests of our directors and executive officers in the Merger, see the section titled “ The Merger—Interests of Certain Persons in the Merger”. Financing of the Merger (Page 51) We anticipate that the total amount of funds necessary to complete the transactions contemplated by the Merger Agreement, and to pay related fees and expenses, will be approximately $945 million.