John T. McDonald

CIK: 0001094792

Transaction Breakdown

Open Market Buys (P)0 (0.0%)

High conviction signal

Open Market Sales (S)1 (4.3%)

Position reduction

Option Exercises (M)6 (26.1%)

Derivative conversions

Awards (A)2 (8.7%)

Compensation grants

Other (G, F, J, C, D, …)14 (60.9%)

Gifts, tax withholding, conversions, dispositions to the issuer and other codes

Companies & Roles (1)

UPLD

Upland Software, Inc.

DirectorOfficer

Discretionary Trading P&L

Holdings

Transaction History (23 total)

UPLD
Upland Software, Inc.
Apr 30, 2026
Award(A)
Direct
250K shares-
UPLD
Upland Software, Inc.
Apr 30, 2026
Disposition(D)
Performance Share Unit
Direct
250K shares-
UPLD
Upland Software, Inc.
Mar 16, 2026
Tax Payment(F)
Direct
18.6K shares at avg. $0.54$10K
UPLD
Upland Software, Inc.
Dec 16, 2025
Tax Payment(F)
Direct
19.7K shares at avg. $1.49$29K
UPLD
Upland Software, Inc.
Sep 16, 2025
Tax Payment(F)
Direct
23K shares at avg. $2.48$57K
UPLD
Upland Software, Inc.
Sep 11, 2025
Sale(S)
Direct
14.4K shares at avg. $2.36$34K
UPLD
Upland Software, Inc.
Jun 16, 2025
Tax Payment(F)
Direct
23K shares at avg. $1.84$42K
UPLD
Upland Software, Inc.
Mar 16, 2025
Tax Payment(F)
Direct
24.3K shares at avg. $3.10$75K
UPLD
Upland Software, Inc.
Jan 28, 2025
Award(A)
Direct
250K shares-
UPLD
Upland Software, Inc.
Dec 16, 2024
Tax Payment(F)
Direct
17.8K shares at avg. $4.51$80K
UPLD
Upland Software, Inc.
Dec 10, 2024
Exercise(M)
Direct
187.5K shares-
UPLD
Upland Software, Inc.
Dec 10, 2024
Tax Payment(F)
Direct
73.8K shares at avg. $5.31$392K
UPLD
Upland Software, Inc.
Dec 9, 2024
Tax Payment(F)
Direct
49.2K shares at avg. $4.89$241K
UPLD
Upland Software, Inc.
Dec 9, 2024
Exercise(M)
Direct
125K shares-
UPLD
Upland Software, Inc.
Dec 6, 2024
Exercise(M)
Direct
187.5K shares-
UPLD
Upland Software, Inc.
Dec 6, 2024
Tax Payment(F)
Direct
73.8K shares at avg. $4.45$328K
UPLD
Upland Software, Inc.
Dec 5, 2024
Exercise(M)
Direct
62.5K shares-
UPLD
Upland Software, Inc.
Dec 5, 2024
Tax Payment(F)
Direct
24.6K shares at avg. $4.32$106K
UPLD
Upland Software, Inc.
Dec 4, 2024
Tax Payment(F)
Direct
12.3K shares at avg. $4.00$49K
UPLD
Upland Software, Inc.
Dec 4, 2024
Exercise(M)
Direct
31.3K shares-
UPLD
Upland Software, Inc.
Dec 3, 2024
Tax Payment(F)
Direct
61.5K shares at avg. $4.37$269K
UPLD
Upland Software, Inc.
Dec 3, 2024
Exercise(M)
Direct
156.3K shares-
UPLD
Upland Software, Inc.
Sep 16, 2024
Tax Payment(F)
Direct
17.8K shares at avg. $2.24$40K

		Type	Shares	Price		Ownership
Apr 30, 2026	UPLD Upland Software, Inc.	Award(A)	250,000	-	$0	Direct
Apr 30, 2026	UPLD Upland Software, Inc.	Disposition(D) Performance Share Unit	250,000	-	-	Direct
Mar 16, 2026	UPLD Upland Software, Inc.	Tax Payment(F)	18,605	$0.54	$10,047	Direct
Dec 16, 2025	UPLD Upland Software, Inc.	Tax Payment(F)	19,677	$1.49	$29,220	Direct
Sep 16, 2025	UPLD Upland Software, Inc.	Tax Payment(F)	22,956	$2.48	$56,931	Direct
Sep 11, 2025	UPLD Upland Software, Inc.	Sale(S)	14,438	$2.36	$34,064	Direct
Jun 16, 2025	UPLD Upland Software, Inc.	Tax Payment(F)	22,957	$1.84	$42,241	Direct
Mar 16, 2025	UPLD Upland Software, Inc.	Tax Payment(F)	24,273	$3.10	$75,246	Direct
Jan 28, 2025	UPLD Upland Software, Inc.	Award(A)	250,000	-	$0	Direct
Dec 16, 2024	UPLD Upland Software, Inc.	Tax Payment(F)	17,833	$4.51	$80,427	Direct
Dec 10, 2024	UPLD Upland Software, Inc.	Exercise(M)	187,500	-	$0	Direct
Dec 10, 2024	UPLD Upland Software, Inc.	Tax Payment(F)	73,781	$5.31	$391,777	Direct
Dec 9, 2024	UPLD Upland Software, Inc.	Tax Payment(F)	49,188	$4.89	$240,529	Direct
Dec 9, 2024	UPLD Upland Software, Inc.	Exercise(M)	125,000	-	$0	Direct
Dec 6, 2024	UPLD Upland Software, Inc.	Exercise(M)	187,500	-	$0	Direct
Dec 6, 2024	UPLD Upland Software, Inc.	Tax Payment(F)	73,781	$4.45	$328,325	Direct
Dec 5, 2024	UPLD Upland Software, Inc.	Exercise(M)	62,500	-	$0	Direct
Dec 5, 2024	UPLD Upland Software, Inc.	Tax Payment(F)	24,594	$4.32	$106,246	Direct
Dec 4, 2024	UPLD Upland Software, Inc.	Tax Payment(F)	12,297	$4.00	$49,188	Direct
Dec 4, 2024	UPLD Upland Software, Inc.	Exercise(M)	31,250	-	$0	Direct
Dec 3, 2024	UPLD Upland Software, Inc.	Tax Payment(F)	61,484	$4.37	$268,685	Direct
Dec 3, 2024	UPLD Upland Software, Inc.	Exercise(M)	156,250	-	$0	Direct
Sep 16, 2024	UPLD Upland Software, Inc.	Tax Payment(F)	17,833	$2.24	$39,946	Direct

1-23 of 23 transactions

About MCDONALD JOHN T

MCDONALD JOHN T (SEC CIK 0001094792) files insider reports with the SEC as CEO of Upland Software, Inc. (UPLD).

Signal8 holds 12 ownership filings by MCDONALD JOHN T, all Form 4s, filed between Sep 17, 2024 and May 4, 2026. Those filings report 23 transactions, from Sep 16, 2024 to Apr 30, 2026. Signal8's Form 4 history starts in Sep 2024.

The business address on MCDONALD JOHN T's filings is in AUSTIN, TX.

Recent filings by MCDONALD JOHN T

Apr 30, 2026: Grant or award of UPLD shares (Form 4, code A).
Apr 30, 2026: Disposition to issuer transaction of UPLD derivative securities (Form 4, code D).
Mar 16, 2026: Tax withholding of UPLD shares (Form 4, code F).
Dec 16, 2025: Tax withholding of UPLD shares (Form 4, code F).
Sep 16, 2025: Tax withholding of UPLD shares (Form 4, code F).

Other insiders filing for Upland Software, Inc. (UPLD)

Doman Dan, Chief Operating & Product Ofcr
Nathaniel Sean, CEO and President
Simon Jennifer L., Chief Financial Officer
Mattox Timothy, Director
Tamez David, Interim CFO
Hill Michael Douglass, CFO, Treasurer & Secretary

How to read Form 4 transaction codes