Cantaloupe CRO Jeffrey Dumbrell Receives $11.20‑Per‑Share Cash in 365 Retail Merger

*TL;DR Jeffrey Dumbrell, Cantaloupe’s chief revenue officer, exchanged all his common shares for $11.20 cash per share and rolled over 20,000 shares into a private partnership as the company closed its all‑cash merger with 365 Retail Markets.

Context Cantaloupe, Inc. (CTLP) finalized an all‑cash acquisition by 365 Retail Markets, converting each outstanding share of Cantaloupe stock into a right to receive $11.20. The transaction marks the end of Cantaloupe’s independent public listing and triggers a series of equity settlements for insiders.

Key Facts - At the merger’s effective time, every Cantaloupe common share held by CRO Jeffrey Dumbrell was cancelled and automatically converted into cash at $11.20 per share. - The Dumbrell Family Trust transferred 20,000 of those shares to Garage Topco LP under a rollover agreement signed shortly before closing, receiving partnership units in exchange. - All in‑the‑money stock options—options with exercise prices below $11.20—were vested and paid out based on the spread between the merger price and the option strike. Options with strike prices at or above $11.20 were cancelled without compensation. - Restricted stock units (RSUs) and performance stock units (PSUs) that were outstanding became fully vested and were converted into cash at the $11.20 rate. - Additional dispositions included the sale of 23,254 common shares on the open market and the cancellation of several non‑qualified stock options.

What It Means The cash payout provides Dumbrell with immediate liquidity, while the rollover of 20,000 shares into Garage Topco LP suggests a continued economic interest in the combined entity. By cancelling out‑of‑the‑money options, the merger eliminates any lingering dilution risk from unexercised warrants. The systematic treatment of all equity awards reflects standard practice in all‑cash acquisitions, where insiders receive cash for vested awards and lose any unvested or underwater options.

Investors will now watch how the merged company integrates Cantaloupe’s technology platform with 365 Retail’s distribution network and whether the new structure delivers the cost synergies projected by management.