# EDGAR Filing Document

**Accession Number:** 0001094792
**File Stem:** 0001094792-23-000002
**Filing Date:** 2023-2
**Character Count:** 7375
**Document Hash:** da8a233a31ec47eeb076fdb962643345
**Contains OCR:** False
**Source Format:** 

## Filing Content

## Filing Summary
**0001094792-23-000002.hdr.sgml**: 20230222

**ACCESSION NUMBER**: 0001094792-23-000002

**CONFORMED SUBMISSION TYPE**: 4

**PUBLIC DOCUMENT COUNT**: 1

**CONFORMED PERIOD OF REPORT**: 20230221

**FILED AS OF DATE**: 20230222

**DATE AS OF CHANGE**: 20230222

**REPORTING-OWNER**: 

**OWNER DATA:**
- **COMPANY CONFORMED NAME:** MCDONALD JOHN T
- **CENTRAL INDEX KEY:** 0001094792

**FILING VALUES:**
- **FORM TYPE:** 4
- **SEC ACT:** 1934 Act
- **SEC FILE NUMBER:** 001-36720
- **FILM NUMBER:** 23653761

**MAIL ADDRESS:**
- **STREET 1:** C/O UPLAND SOFTWARE INC.
- **STREET 2:** 401 CONGRESS AVE., SUITE 1850
- **CITY:** AUSTIN
- **STATE:** TX
- **ZIP:** 78701
**ISSUER**: 

**COMPANY DATA:**
- **COMPANY CONFORMED NAME:** Upland Software, Inc.
- **CENTRAL INDEX KEY:** 0001505155
- **STANDARD INDUSTRIAL CLASSIFICATION:** SERVICES-PREPACKAGED SOFTWARE [7372]
- **IRS NUMBER:** 272992077
- **STATE OF INCORPORATION:** TX
- **FISCAL YEAR END:** 1231

**BUSINESS ADDRESS:**
- **STREET 1:** 401 CONGRESS AVE.
- **STREET 2:** SUITE 1850
- **CITY:** AUSTIN
- **STATE:** TX
- **ZIP:** 78701
- **BUSINESS PHONE:** 512-960-1010

**MAIL ADDRESS:**
- **STREET 1:** 401 CONGRESS AVE.
- **STREET 2:** SUITE 1850
- **CITY:** AUSTIN
- **STATE:** TX
- **ZIP:** 78701

**FORMER COMPANY:**
- **FORMER CONFORMED NAME:** Silverback Acquisition Corp
- **DATE OF NAME CHANGE:** 20101105

### UNITED STATES SECURITIES AND EXCHANGE COMMISSION
**Washington, D.C. 20549**

## FORM 4

### STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

[ ] Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

[ ] Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

---

| | | |
|:---|:---|:---|
| **1. Name and Address of Reporting Person**<sup>*</sup><br>MCDONALD JOHN T<br><sub>(Last) (First) (Middle)</sub><br>401 CONGRESS AVE., STE 1850<br><sub>(Street)</sub><br>AUSTIN, TX 78701<br><sub>(City) (State) (Zip)</sub> | **3. Date of Earliest Transaction (Month/Day/Year)**<br>2023-02-21 | **5. Relationship of Reporting Person(s) to Issuer**<br>(Check all applicable)<br>[X] Director [ ] 10% Owner<br>[X] Officer (give title below) [ ] Other (specify below)<br>_CEO_ |
| **2. Issuer Name and Ticker or Trading Symbol**<br>Upland Software, Inc. [ UPLD ] | **4. If Amendment, Date of Original Filed (Month/Day/Year)**<br>  | **6. Individual or Joint/Group Filing (Check Applicable Line)**<br>[X] Form filed by One Reporting Person<br>[ ] Form filed by More than One Reporting Person |

---

## Table I - Non-Derivative Securities

---

|  |  |  |  |  |  |  |  |  |  |  |
| --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- |
| 1. Title of Security | 2. Transaction Date | 2A. Deemed Execution Date | 3. Transaction Code (V) | 3. Transaction Code (V) | 4. Securities Acquired (A) or Disposed of (D) | 4. Securities Acquired (A) or Disposed of (D) | 4. Securities Acquired (A) or Disposed of (D) | 5. Amount of Securities Beneficially Owned | 6. Ownership Form | 7. Nature of Indirect Beneficial Ownership |
| 1. Title of Security | 2. Transaction Date | 2A. Deemed Execution Date | Code | V | Amount | (A) or (D) | Price | 5. Amount of Securities Beneficially Owned | 6. Ownership Form | 7. Nature of Indirect Beneficial Ownership |
| Common Stock | 2023-02-21 |  | A |  | 100000<sup>(1)</sup> | A | $0 | 1679402<sup>(2)</sup> | D |  |
| Common Stock |  |  |  |  |  |  |  | 243738 | I | By National Financial Services as Cust FBO J. McDonald RRA |

---

## Table II - Derivative Securities

---

|  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
| --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- |
| 1. Title of Derivative Security | 2. Conversion or Exercise Price | 3. Transaction Date | 3A. Deemed Execution Date | 4. Transaction Code (V) | 4. Transaction Code (V) | 5. Number of Derivative Securities Acquired (A) or Disposed of (D) | 5. Number of Derivative Securities Acquired (A) or Disposed of (D) | 6. Date Exercisable and Expiration Date | 6. Date Exercisable and Expiration Date | 7. Title and Amount of Underlying Securities | 7. Title and Amount of Underlying Securities | 8. Price of Derivative Security | 9. Number of Derivative Securities Beneficially Owned | 10. Ownership Form | 11. Nature of Indirect Beneficial Ownership |
| 1. Title of Derivative Security | 2. Conversion or Exercise Price | 3. Transaction Date | 3A. Deemed Execution Date | Code | V | (A) | (D) | Date Exercisable | Expiration Date | Title | Amount or Number of Shares | 8. Price of Derivative Security | 9. Number of Derivative Securities Beneficially Owned | 10. Ownership Form | 11. Nature of Indirect Beneficial Ownership |
| Performance Share Unit | $0.0 |  |  |  |  |  |  | <sup>(3)</sup> | 2023-06-30<sup>(3)</sup> | Common Stock | 93750.0 |  | 93750 | D |  |
| Performance Share Unit | $0.0 | 2023-02-21 |  | A |  | 100000 |  | <sup>(4)</sup> | 2025-12-31<sup>(4)</sup> | Common Stock | 100000.0 | $0 | 100000 | D |  |

---

### Footnotes:

(1) Represents restricted stock units vesting in twelve equal quarterly installments starting on March 16, 2023 and ending on December 16, 2025; provided that the participant continues to be a service provider through each such vesting date.

(2) Does not include 125,000 shares of common stock held in a trust for the benefit of Mr. McDonald's children of which The Bryn Mawr Trust Company of Delaware is the trustee.

(3) Units will vest on the first date on which the closing price of Upland's common stock for any 30 consecutive trading days immediately preceding such date before June 30, 2023 equals or exceeds certain stock price hurdles. On June 30, 2023, a number of Units (if any) will vest based on the closing price of Upland's common stock on June 30, 2023 using linear interpolation. Total shares earned will be between 0% and 300% of the target number of shares reported.

(4) Units will vest on the first date on which the closing price of Upland's common stock for any 30 consecutive trading days immediately preceding such date before December 31, 2025 equals or exceeds certain stock price hurdles. On December 31, 2025, a number of Units (if any) will vest based on the closing price of Upland's common stock on December 31, 2025 using linear interpolation. Total shares earned will be between 0% and 200% of the target number of shares reported.

**Signature:** /s/ Kin Gill, as attorney-in-fact for Mr. McDonald  
**Date:** 2023-02-22

### Remarks:

Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.

* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).

** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).

Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.

**Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.**