Company: CTLPP
Filing Date: 2025-10-10
Form Type: DEF 14A
Source: 0001628280-25-044777
Chunk: 24

Company: CANTALOUPE, INC.
Filing Date: 2025-10-10
Form: DEF 14A
Chunk 24
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 and outstanding shares of Common Stock and Series A Preferred Stock voting together (with each share of Common Stock entitled to one vote, and each share of Series A Preferred Stock entitled to 0.1988 of a vote, with any fractional vote being rounded to the nearest whole number) is required for approval of this proposal.

| The Board of Directors recommends that you vote, on an advisory basis,“FOR”the proposal to approve the compensation of the named executive officers. |

#### 2026Proxy Statement44

### Compensation Discussion & Analysis
The following Compensation Discussion and Analysis (“CD&A”) provides information regarding our executive compensation philosophy, the elements of our executive compensation program, and the factors that were considered in the compensation actions and decisions for our named executive officers during fiscal 2025. The CD&A should be read together with the compensation tables and related disclosures set forth elsewhere in this proxy statement.

Our Compensation Committee has been actively restructuring our compensation programs since fiscal 2022 and through fiscal 2025 to accommodate changes in our management team and to design and implement a program that the Compensation Committee believes aligns with the Company’s long-term strategic plan, reflects our pay-for-performance philosophy, encourages retention of key executives, and increases alignment between the interests of our executives and our shareholders.

#### Our Named Executive Officers
During fiscal 2025, our named executive officers (“NEOs”) were as follows:

| Ravi Venkatesan         
 Chief Executive Officer |     | Scott Stewart           
 Chief Financial Officer |     | Jeffrey Dumbrell      
 Chief Revenue Officer |     | Gaurav Singal                      
 Former Chief Technology Officer(1) |     | Anna Novoseletsky                  
 Chief Legal and Compliance Officer |

(1) Mr. Singal resigned from the Company, effective as of October 7, 2025.

#### 452026Proxy Statement
Compensation Discussion & Analysis

#### Table of Contents
| Compensation Discussion & Analysis        |     | 45 |
| CD&A At-A-Glance                          |     | 47 |
| Our Compensation Philosophy               |     | 47 |
| Compensation Process                      |     | 50 |
| Fiscal Year 2025 Executive Compensation   |     | 51 |
| Executive Officer Employment Arrangements |     | 58 |
| Compensation Policies and Practices       |     | 60 |
| Compensation Committee Report             |     | 61 |

| Executive Compensation Tables and Related Disclosures     |     | 62 |
| Summary Compensation Table                                |     | 62 |
| Grants of