Company: CTLPP
Filing Date: 2025-07-24
Form Type: DEFM14A
Source: 0001140361-25-027048
Chunk: 21

Company: CANTALOUPE, INC.
Filing Date: 2025-07-24
Form: DEFM14A
Chunk 21
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 Cantaloupe Restricted Stock Awards held by our executive officers will become fully vested and converted into the right to receive an amount in cash equal to the merger consideration. |

| • | Cantaloupe PSUs held by our executive officers will vest based on the deemed achievement of the performance metrics at target performance for incomplete performance periods. Immediately thereafter, Cantaloupe PSUs will be converted into the right to receive an amount in cash equal to the merger consideration. |

| • | Cantaloupe’s directors and executive officers are entitled to continued indemnification and insurance coverage following completion of the Merger under existing indemnification agreements and 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, 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. |

| • | Prior to the effective time of the Merger, certain of our executive officers may enter into