UPLD

SEC source: 0001422137-24-000004 · wk-form4_1710886298.xml · nonDerivative · entry 1

Smith Matthew Harnden · CIK 0001422137 · General Counsel and Secretary

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 98,536

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

SEC source: 0001289889-24-000004 · wk-form4_1710886503.xml · nonDerivative · entry 1

Hill Michael Douglass · CIK 0001289889 · CFO & Treasurer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 338,245

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

SEC source: 0001342356-24-000004 · wk-form4_1710886023.xml · nonDerivative · entry 1

Cummings Karen · CIK 0001342356 · President and COO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 390,994

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

SEC source: 0001940842-24-000004 · wk-form4_1710885854.xml · nonDerivative · entry 1

Doman Dan · CIK 0001940842 · Chief Product Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 326,013

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

SEC source: 0002011142-24-000004 · wk-form4_1707346978.xml · nonDerivative · entry 1

Breslin Matthew · CIK 0002011142 · Chief Revenue Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 150,000

F1 · shares: One third (33.33%) of the shares of Common Stock subject to the Restricted Stock Unit Award shall vest on 3/16/2025, one-third (33.33%) of the shares of Common Stock subject to the Restricted Stock Unit Award shall vest on 3/16/2026 the remainder (33.34%) of the shares of Common Stock subject to the Restricted Stock Unit Award shall vest on 3/16/2027.

SEC source: 0001094792-24-000003 · wk-form4_1706747025.xml · derivative · entry 3

MCDONALD JOHN T · CIK 0001094792 · Director · CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 250,000

Underlying: Common Stock · 250,000 shares

Expires 2025-08-28

F3 · derivative.exercise_date: 0% to 300% of these PSUs may vest based on the achievement of the Company's TSR goals for any 30 consecutive trading days immediately preceding any such date during the period beginning on February 28, 2024 and ending on August 28, 2025- the Performance Period. The percentage of PSUs that may vest will be a- 0% if TSR is below 5% b- 50% if TSR is 5% c- 100% if TSR is 10% and d- 300% if TSR is 20% or greater. The percentage of PSUs that may vest is determined using linear interpolation. The PSUs earned shall be limited to the number of shares available for issuance under the 2014 Equity Incentive Plan on the applicable vesting date. If the Company's stockholders approve an equity incentive plan at the 2024 annual meeting and pursuant to such plan, the Reporting Person is granted an award of PSUs prior to the end of the Performance Period, the PSUs earned pursuant to the vesting schedule shall be limited to 250,000 PSUs.

SEC source: 0001094792-24-000003 · wk-form4_1706747025.xml · nonDerivative · entry 1

MCDONALD JOHN T · CIK 0001094792 · Director · CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,881,748

F1 · shares: The RSUs vest in twelve equal quarterly installments starting on the three month anniversary of the Vesting Commencement Date of December 16, 2023 provided that, except as otherwise provided in the Executive Employment Agreement between the Company and Participant, the Participant continues to be a Service Provider through each such vesting date.

F2 · balance_after: 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.

SEC source: 0001984088-24-000002 · wk-form4_1706741677.xml · nonDerivative · entry 1

Yates Oliver Robert MacFarlane · CIK 0001984088 · Chief Sales Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 258,239

F1 · shares: The RSUs vest in twelve equal quarterly installments starting on the three (3) month anniversary of the Vesting Commencement Date of December 16, 2023, provided that the Participant continues to be a Service Provider through each such vesting date. Notwithstanding the foregoing, in the event of the Participant's termination by the Company for any reason other than cause or if Participant leaves for Good Reason after a Change in Control (as defined in the Plan), then 100% of the RSUs shall become fully vested.

SEC source: 0001422137-24-000002 · wk-form4_1706741386.xml · nonDerivative · entry 1

Smith Matthew Harnden · CIK 0001422137 · General Counsel and Secretary

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 100,000

F1 · shares: The RSUs vest in twelve equal quarterly installments starting on the three (3) month anniversary of the Vesting Commencement Date of December 16, 2023, provided that the Participant continues to be a Service Provider through each such vesting date. Notwithstanding the foregoing, in the event of the Participant's termination by the Company for any reason other than cause or if Participant leaves for Good Reason after a Change in Control (as defined in the Plan), then 100% of the RSUs shall become fully vested.

SEC source: 0001289889-24-000002 · wk-form4_1706741561.xml · nonDerivative · entry 1

Hill Michael Douglass · CIK 0001289889 · CFO & Treasurer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 350,804

F1 · shares: The RSUs vest in twelve equal quarterly installments starting on the three (3) month anniversary of the Vesting Commencement Date of December 16, 2023, provided that the Participant continues to be a Service Provider through each such vesting date. Notwithstanding the foregoing, in the event of the Participant's termination by the Company for any reason other than cause or if Participant leaves for Good Reason after a Change in Control (as defined in the Plan), then 100% of the RSUs shall become fully vested.

SEC source: 0001342356-24-000002 · wk-form4_1706741829.xml · nonDerivative · entry 1

Cummings Karen · CIK 0001342356 · Executive VP & Senior GM

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 400,509

F1 · shares: The RSUs vest in twelve equal quarterly installments starting on the three (3) month anniversary of the Vesting Commencement Date of December 16, 2023; provided that, except as otherwise provided in the Executive Employment Agreement between the Company and Participant, the Participant continues to be a Service Provider through each such vesting date.

SEC source: 0001940842-24-000002 · wk-form4_1706742097.xml · nonDerivative · entry 1

Doman Dan · CIK 0001940842 · Chief Product Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 341,271

F1 · shares: The RSUs vest in twelve equal quarterly installments starting on the three (3) month anniversary of the Vesting Commencement Date of December 16, 2023, provided that the Participant continues to be a Service Provider through each such vesting date. Notwithstanding the foregoing, in the event of the Participant's termination by the Company for any reason other than cause or if Participant leaves for Good Reason after a Change in Control (as defined in the Plan), then 100% of the RSUs shall become fully vested.

SEC source: 0001094792-24-000006 · wk-form4a_1710191726.xml · derivative · entry 3

MCDONALD JOHN T · CIK 0001094792 · Director · CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 250,000

Underlying: Common Stock · 250,000 shares

Expires 2027-02-28

F3 · derivative.exercise_date: 0% to 300% of these PSUs may vest based on the achievement of the Company's TSR goals for any 30 consecutive trading days immediately preceding any such date during the period beginning on February 28, 2024 and ending on February 28, 2027- the Performance Period. The percentage of PSUs that may vest will be a- 0% if TSR is below 5% b- 50% if TSR is 5% c- 100% if TSR is 10% and d- 300% if TSR is 20% or greater. The percentage of PSUs that may vest is determined using linear interpolation. The PSUs earned shall be limited to the number of shares available for issuance under the 2014 Equity Incentive Plan on the applicable vesting date. If the Company's stockholders approve an equity incentive plan at the 2024 annual meeting and pursuant to such plan, the Reporting Person is granted an award of PSUs prior to the end of the Performance Period, the PSUs earned pursuant to the vesting schedule shall be limited to 250,000 PSUs.

F4 · derivative.exercise_date: On January 31, 2024, the Reporting Person filed a Form 4 which inadvertently reported that the Performance Period ended on August 28, 2025. Footnote 3 above and column 6 above have been amended to reflect that the Performance Period ends on February 28, 2027.

SEC source: 0001094792-24-000006 · wk-form4a_1710191726.xml · nonDerivative · entry 1

MCDONALD JOHN T · CIK 0001094792 · Director · CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,881,748

F1 · shares: The RSUs vest in twelve equal quarterly installments starting on the three month anniversary of the Vesting Commencement Date of December 16, 2023 provided that, except as otherwise provided in the Executive Employment Agreement between the Company and Participant, the Participant continues to be a Service Provider through each such vesting date.

F2 · balance_after: 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.

SEC source: 0001624067-24-000003 · wk-form4_1704762291.xml · nonDerivative · entry 1

Mattox Timothy · CIK 0001624067 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 411,776

F1 · price: Represents restricted stock units vesting in 4 equal installments on each of 3/16/2024, 6/16/2024, 9/16/2024 and 12/16/2024, provided Mr. Mattox continues to serve as a Director of Upland Software, Inc. (the "Issuer") as of each date.

SEC source: 0001094792-23-000009 · wk-form4_1703025395.xml · nonDerivative · entry 1

MCDONALD JOHN T · CIK 0001094792 · Director · CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,631,748

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

F2 · balance_after: 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.

SEC source: 0001984088-23-000006 · wk-form4_1703023919.xml · nonDerivative · entry 1

Yates Oliver Robert MacFarlane · CIK 0001984088 · Chief Sales Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 123,239

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

SEC source: 0001941688-23-000008 · wk-form4_1703025885.xml · nonDerivative · entry 1

Miller Paul Kenneth · CIK 0001941688 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 209,387

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

SEC source: 0001289889-23-000007 · wk-form4_1703023789.xml · nonDerivative · entry 1

Hill Michael Douglass · CIK 0001289889 · CFO & Treasurer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 250,804

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock. This is not an open market sale of securities.

SEC source: 0001342356-23-000007 · wk-form4_1703025155.xml · nonDerivative · entry 1

Cummings Karen · CIK 0001342356 · Executive VP & Senior GM

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 250,509

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

SEC source: 0001940842-23-000006 · wk-form4_1703025272.xml · nonDerivative · entry 1

Doman Dan · CIK 0001940842 · Chief Product Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 191,271

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock. This is not an open market sale of securities.

SEC source: 0001131058-23-000003 · wk-form4_1700684833.xml · nonDerivative · entry 1

COURTER STEPHEN E · CIK 0001131058 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 74,232

F1 · price: This transaction was executed in multiple trades at prices ranging from $4.315 to $4.68; the price reported above reflects the weighted average sale price. The reporting person hereby undertakes to provide full information regarding the number of shares and prices at which the transactions were effected upon request to the SEC staff, Upland Software, or a security holder of Upland Software.

SEC source: 0001628280-23-038306 · wk-form4_1699566618.xml · nonDerivative · entry 1

Doman Dan · CIK 0001940842 · Chief Product Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 199,779

F1 · price: This transaction was executed in multiple trades at prices ranging from $4.71 to $4.89; the price reported above reflects the weighted average sale price. The reporting person hereby undertakes to provide full information regarding the number of shares and prices at which the transactions were effected upon request to the SEC staff, Upland Software, or a security holder of Upland Software.

SEC source: 0001628280-23-036081 · wk-form4_1698876215.xml · nonDerivative · entry 1

Smith Matthew Harnden · CIK 0001422137 · General Counsel and Secretary

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 50,000

F1 · shares: Represents restricted stock units vesting as follows: One third (33.33%) of the shares of Common Stock shall vest on December 16, 2024, one-third (33.33%) of the shares of Common Stock shall vest on December 16, 2025, the remainder (33.34%) of the shares of Common Stock shall vest on December 16, 2026; provided that the participant continues to be a service provider through each such vesting date.

SEC source: 0001094792-23-000007 · wk-form4_1695168102.xml · nonDerivative · entry 1

MCDONALD JOHN T · CIK 0001094792 · Director · CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,643,398

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock. This is not an open market sale of securities.

F2 · balance_after: 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.

SEC source: 0001984088-23-000004 · wk-form4_1695157639.xml · nonDerivative · entry 1

Yates Oliver Robert MacFarlane · CIK 0001984088 · Chief Sales Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 125,979

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock. This is not an open market sale of securities.

SEC source: 0001628280-23-032559 · wk-form4_1695161643.xml · nonDerivative · entry 1

Miller Paul Kenneth · CIK 0001941688 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 215,948

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock. This is not an open market sale of securities.

SEC source: 0001289889-23-000004 · wk-form4_1695158074.xml · nonDerivative · entry 1

Hill Michael Douglass · CIK 0001289889 · CFO & Treasurer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 260,808

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock. This is not an open market sale of securities.

SEC source: 0001342356-23-000005 · wk-form4_1695158370.xml · nonDerivative · entry 1

Cummings Karen · CIK 0001342356 · Executive VP & Senior GM

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 255,788

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock. This is not an open market sale of securities.

SEC source: 0001628280-23-032553 · wk-form4_1695160861.xml · nonDerivative · entry 1

Doman Dan · CIK 0001940842 · Chief Product Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 213,775

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock. This is not an open market sale of securities.

SEC source: 0001629817-23-000004 · wk-form4_1695158281.xml · nonDerivative · entry 1

Gill Kinloch III · CIK 0001629817 · CLO and Secretary

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 194,590

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock. This is not an open market sale of securities.

SEC source: 0001131058-23-000001 · wk-form4_1691008114.xml · nonDerivative · entry 1

COURTER STEPHEN E · CIK 0001131058 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 94,680

F1 · shares: Represents restricted stock units vesting in 4 equal installments on each of 9/16/2023, 12/16/2023, 3/16/2024 and 6/16/2024.

SEC source: 0001805725-23-000001 · wk-form4_1691008342.xml · nonDerivative · entry 1

Walsh Teresa Miles · CIK 0001805725 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 94,490

F1 · shares: Represents restricted stock units vesting in 4 equal installments on each of 9/16/2023, 12/16/2023, 3/16/2024 and 6/16/2024.

SEC source: 0001458635-23-000001 · wk-form4_1691007984.xml · nonDerivative · entry 1

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 141,437

F1 · shares: Represents restricted stock units vesting in 4 equal installments on each of 9/16/2023, 12/16/2023, 3/16/2024 and 6/16/2024.

SEC source: 0001576150-23-000004 · wk-form4_1691019907.xml · nonDerivative · entry 1

Chung David H S · CIK 0001576150 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 74,484

F1 · shares: Represents restricted stock units vesting in 4 equal installments on each of 9/16/2023, 12/16/2023, 3/16/2024 and 6/16/2024, provided Mr. Chung continues to serve as a Director of Upland Software, Inc. (the "Issuer") as of each date. Upon any subsequent disposition of common stock of the Issuer covered by the RSUs, Mr. Chung will transfer the proceeds from any such disposition to HGGC, LLC or its affiliates ("HGGC") as required by an agreement between Mr. Chung and HGGC. As such, Mr. Chung disclaims all pecuniary interest in the reported securities.

SEC source: 0001719895-23-000001 · wk-form4_1691008240.xml · nonDerivative · entry 1

Ross Joe · CIK 0001719895 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 118,545

F1 · shares: Represents restricted stock units vesting in 4 equal installments on each of 9/16/2023, 12/16/2023, 3/16/2024 and 6/16/2024.

SEC source: 0000950170-23-028921 · ownership.xml · nonDerivative · entry 1

MCDONALD JOHN T · CIK 0001094792 · Director · CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,655,048

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

F2 · balance_after: 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.

SEC source: 0000950170-23-028926 · ownership.xml · nonDerivative · entry 1

Miller Paul Kenneth · CIK 0001941688 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 222,509

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

SEC source: 0000950170-23-028951 · ownership.xml · nonDerivative · entry 1

Hill Michael Douglass · CIK 0001289889 · CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 270,812

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

SEC source: 0000950170-23-028939 · ownership.xml · nonDerivative · entry 1

Doman Dan · CIK 0001940842 · Chief Product Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 222,303

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

SEC source: 0000950170-23-028937 · ownership.xml · nonDerivative · entry 1

Gill Kinloch III · CIK 0001629817 · CLO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 201,314

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

SEC source: 0001094792-23-000005 · wf-form4_167935273220570.xml · nonDerivative · entry 1

MCDONALD JOHN T · CIK 0001094792 · Director · CEO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,666,698

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock. This is not an open market sale of securities.

F2 · balance_after: 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.

SEC source: 0001941688-23-000004 · wf-form4_167935256945062.xml · nonDerivative · entry 1

Miller Paul Kenneth · CIK 0001941688 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 229,070

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock. This is not an open market sale of securities.

SEC source: 0001289889-23-000003 · wf-form4_167935317950545.xml · nonDerivative · entry 1

Hill Michael Douglass · CIK 0001289889 · CFO & Treasurer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 280,816

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock. This is not an open market sale of securities.

SEC source: 0001940842-23-000004 · wf-form4_167935266567043.xml · nonDerivative · entry 1

Doman Dan · CIK 0001940842 · Chief Product Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 230,831

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock. This is not an open market sale of securities.

SEC source: 0001629817-23-000003 · wf-form4_167935249139075.xml · nonDerivative · entry 1

Gill Kinloch III · CIK 0001629817 · CLO and Secretary

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 208,038

F1 · kind: Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock. This is not an open market sale of securities.

SEC source: 0001094792-23-000004 · wf-form4_167882452446754.xml · nonDerivative · entry 3

MCDONALD JOHN T · CIK 0001094792 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Indirect · By National Financial Services as Cust FBO J. McDonald RRA

Disclosed balance after: 263,738

SEC source: 0001094792-23-000004 · wf-form4_167882452446754.xml · nonDerivative · entry 2

MCDONALD JOHN T · CIK 0001094792 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Indirect · By National Financial Services as Cust FBO J. McDonald RRA

Disclosed balance after: 253,738

SEC source: 0001094792-23-000002 · wf-form4_167710170573567.xml · derivative · entry 4

MCDONALD JOHN T · CIK 0001094792 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 100,000

Underlying: Common Stock · 100,000 shares

Expires 2025-12-31

F4 · derivative.exercise_date: 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.

F4 · derivative.expiration_date: 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.

SEC source: 0001094792-23-000002 · wf-form4_167710170573567.xml · nonDerivative · entry 1

MCDONALD JOHN T · CIK 0001094792 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,679,402

F1 · shares: 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.

F2 · balance_after: 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.