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Upland Software (NASDAQ: UPLD) director shifts 250,000 PSUs into new 250,000 RSU grant

Filing Impact
(Neutral)
Filing Sentiment
(Neutral)
Form Type
4

Rhea-AI Filing Summary

Upland Software director John T. McDonald reported equity compensation changes involving common stock and performance share units. He received a grant of 250,000 restricted stock units, which will vest on the earliest of February 28, 2028, his termination from the board without Cause as defined in his employment agreement, or a Change in Control under the company’s 2024 Omnibus Incentive Plan. At the same time, 250,000 performance stock units were canceled effective April 30, 2026 under a Transition Agreement between McDonald and the company. Following these transactions, he holds 2,640,887 shares of common stock directly and 363,738 shares indirectly through a custodial account, in addition to 125,000 shares held in a trust for his children that are noted but not included in the reported totals.

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Insider MCDONALD JOHN T
Role null
Type Security Shares Price Value
Disposition Performance Share Unit 250,000 $0.00 --
Grant/Award Common Stock 250,000 $0.00 --
holding Common Stock -- -- --
Holdings After Transaction: Performance Share Unit — 0 shares (Direct, null); Common Stock — 2,640,887 shares (Direct, null); Common Stock — 363,738 shares (Indirect, By National Financial Services as Cust FBO J. McDonald RRA)
Footnotes (1)
  1. The restricted stock units will vest on the earliest of (i) February 28, 2028, subject to Mr. McDonald's continued service on the Issuer's board of directors through such date, (ii) the termination of his service on the Board without Cause, as that term is defined in Mr. McDonald's employment agreement and (iii) a Change in Control, as defined in the Issuer's 2024 Omnibus Incentive Plan. 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. The performance stock units canceled effective April 30, 2026 in accordance with that certain Transition Agreement dated February 25, 2026 by and between the Issuer and Mr. McDonald.
Restricted stock unit grant 250,000 units at $0.0000 Common Stock grant on April 30, 2026
Performance stock units canceled 250,000 units Canceled effective April 30, 2026
Direct holdings after transaction 2,640,887 shares Common Stock held directly by McDonald
Indirect custodial holdings 363,738 shares Held by National Financial Services as custodian
Trust holdings for children 125,000 shares Held in trust with Bryn Mawr Trust Company of Delaware as trustee
RSU vesting date February 28, 2028 Earliest scheduled vesting date for restricted stock units
restricted stock units financial
"The restricted stock units will vest on the earliest of (i) February 28, 2028"
Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.
performance stock units financial
"The performance stock units canceled effective April 30, 2026"
Performance stock units are a type of company award that grants employees shares of stock only if certain performance goals are met. They motivate employees to work toward specific company achievements, aligning their interests with those of shareholders. For investors, they can influence a company's future stock supply and reflect management’s confidence in reaching key targets.
Change in Control financial
"and (iii) a Change in Control, as defined in the Issuer's 2024 Omnibus Incentive Plan"
A "change in control" occurs when the ownership or management of a company shifts significantly, such as through a merger, acquisition, or sale of a large part of its assets. This change can impact how the company is run and may influence its future direction. For investors, it matters because it can affect the company's stability, strategy, and value, often signaling potential changes in investment risk or opportunity.
Transition Agreement financial
"in accordance with that certain Transition Agreement dated February 25, 2026"
2024 Omnibus Incentive Plan financial
"as defined in the Issuer's 2024 Omnibus Incentive Plan"
Form 4 Insider Transactions: What Each Field Means →
SEC Form 4
FORM 4UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940
OMB APPROVAL
OMB Number:3235-0287
Estimated average burden
hours per response:0.5
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*
MCDONALD JOHN T
(Last)(First)(Middle)
900 S. CAPITAL OF TEXAS HWY
LAS CIMAS IV, SUITE 300
(Street)
AUSTIN TEXAS 78746
(City)(State)(Zip)
UNITED STATES
(Country)		2. Issuer Name and Ticker or Trading Symbol
Upland Software, Inc. [ UPLD ] 		5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
XDirector10% Owner
Officer (give title below)Other (specify below)
2a. Foreign Trading Symbol
3. Date of Earliest Transaction (Month/Day/Year)
04/30/2026		6. Individual or Joint/Group Filing (Check Applicable Line)
XForm filed by One Reporting Person
Form filed by More than One Reporting Person
4. If Amendment, Date of Original Filed (Month/Day/Year)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3) 2. Transaction Date (Month/Day/Year)2A. Deemed Execution Date, if any (Month/Day/Year)3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4)
CodeVAmount(A) or (D)Price
Common Stock04/30/2026A250,000(1)A$02,640,887D
Common Stock363,738IBy National Financial Services as Cust FBO J. McDonald RRA(2)
Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned
(e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (Month/Day/Year)3A. Deemed Execution Date, if any (Month/Day/Year)4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 6. Date Exercisable and Expiration Date (Month/Day/Year)7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount or Number of Shares
Performance Share Unit$004/30/2026D250,000 (3) (3)Common Stock250,000$00D
Explanation of Responses:
1. The restricted stock units will vest on the earliest of (i) February 28, 2028, subject to Mr. McDonald's continued service on the Issuer's board of directors through such date, (ii) the termination of his service on the Board without Cause, as that term is defined in Mr. McDonald's employment agreement and (iii) a Change in Control, as defined in the Issuer's 2024 Omnibus Incentive Plan.
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. The performance stock units canceled effective April 30, 2026 in accordance with that certain Transition Agreement dated February 25, 2026 by and between the Issuer and Mr. McDonald.
Remarks:
/s/ Michael D. Hill (as attorney-in-fact for J. McDonald)05/04/2026
** Signature of Reporting PersonDate
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.
* Form 4: SEC 1474 (03-26)

Source: View Original Filing on SEC EDGAR

FAQ

What insider transactions did Upland Software (UPLD) director John T. McDonald report?

John T. McDonald reported receiving 250,000 restricted stock units and the cancellation of 250,000 performance stock units. These changes are part of his equity compensation and reflect a shift from performance-based units to time- and event-based restricted stock units.

How many Upland Software (UPLD) shares does John T. McDonald hold after this Form 4?

After these transactions, McDonald holds 2,640,887 Upland Software common shares directly and 363,738 shares indirectly via a custodial account. The filing also notes 125,000 additional shares held in a trust for his children, which are disclosed separately from the reported totals.

When do John T. McDonald’s new Upland Software restricted stock units vest?

The 250,000 restricted stock units vest on the earliest of February 28, 2028, his termination from the board without Cause, or a Change in Control under Upland Software’s 2024 Omnibus Incentive Plan. Vesting remains subject to his continued board service through the applicable date.

What happened to John T. McDonald’s Upland Software performance stock units?

250,000 performance stock units were canceled effective April 30, 2026. The filing links this cancellation to a Transition Agreement dated February 25, 2026 between Upland Software and McDonald, indicating those performance-based awards are no longer outstanding after that date.

How are John T. McDonald’s indirect Upland Software holdings structured?

The Form 4 shows 363,738 Upland Software shares held indirectly through National Financial Services as custodian for a J. McDonald retirement account. It also notes 125,000 shares held in a separate trust for his children, with The Bryn Mawr Trust Company of Delaware serving as trustee.

What conditions affect vesting of John T. McDonald’s Upland Software restricted stock units?

Vesting of the 250,000 restricted stock units depends on his continued board service to February 28, 2028. Alternatively, vesting can be triggered earlier by a termination from the board without Cause or by a Change in Control, each defined in governing company agreements.