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MAY DAVID

Disclosed activity across 1 company

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73806
SEC CIK
0001458635

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Reported relationships

Latest disclosed role at each company.

CompanyLast reported asReport datePublished
Upland Software, Inc.UPLD · Entity 7891DirectorOctober 27, 2025October 29, 2025

Disclosed balances

About these balances

Latest available filing per company, not a reconstructed current portfolio. Matching sequences show the last reported balance with all source rows expandable; grouping alone does not establish account ownership. Do not add unresolved positions together. Filings may omit unchanged positions, and amendments may correct only part of an older disclosure. Jointly reported shares are not necessarily this owner's personal holdings.

Upland Software, Inc.

Report date October 27, 2025 · Filed October 29, 2025

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
Common StockSEC Table I · non-derivativeDirect191,437 Reported balance After 2025-10-27 transaction · row 1
1 source row

Row 1 · 2025-10-27 · Grant · Acquired 25,000 · Balance 191,437

F1: Represents restricted stock units vesting as follows: one-half (1/2) shall vest on 12/16/25 and the remaining shall in two equal quarterly installments on each of 3/16/26 and 6/16/26.

Filing footnotes · ownership attribution and instrument terms

F1: Represents restricted stock units vesting as follows: one-half (1/2) shall vest on 12/16/25 and the remaining shall in two equal quarterly installments on each of 3/16/26 and 6/16/26.

Transaction history

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Purchases/sales include open-market and private transactions. Plan disclosure applies to the filing; individual rows may differ. “Not disclosed” is not “unplanned.”

The cutoff filters transaction history only. Company summaries and owner relationships show the latest available disclosures. Parser corrections can improve historical records.

Transaction dateCompanyActivity / securityShares / unitsReported priceReported valueDetails
October 27, 2025 Filed Oct 29, 2025 16:32 UTC Upland Software, Inc. UPLD · Entity 7891 GrantCommon Stock 25,000 $0.00 $0.00
Disclosure

SEC source: 0001458635-25-000002 · wk-form4_1761769952.xml · nonDerivative · entry 1

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 191,437

F1 · shares: Represents restricted stock units vesting as follows: one-half (1/2) shall vest on 12/16/25 and the remaining shall in two equal quarterly installments on each of 3/16/26 and 6/16/26.

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November 04, 2024 Filed Nov 4, 2024 17:08 UTC Upland Software, Inc. UPLD · Entity 7891 GrantCommon Stock 25,000 $0.00 $0.00
Disclosure

SEC source: 0001458635-24-000003 · wk-form4_1730758128.xml · nonDerivative · entry 1

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 166,437

F1 · shares: Represents restricted stock units vesting as follows: one-half (1/2) shall vest on 12/16/24 and the remaining shall vest in two equal quarterly installments on each of 3/16/25 and 6/16/25.

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July 31, 2023 Filed Aug 2, 2023 16:26 UTC Upland Software, Inc. UPLD · Entity 7891 GrantCommon Stock 62,816 $0.00 $0.00
Disclosure

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.

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August 01, 2022 Filed Aug 2, 2022 17:20 UTC Upland Software, Inc. UPLD · Entity 7891 GrantCommon Stock 17,830 $0.00 $0.00
Disclosure

SEC source: 0001458635-22-000003 · wf-form4_165947518862346.xml · nonDerivative · entry 1

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 78,621

F1 · shares: Represents restricted stock units vesting in 4 equal installments on each of 9/16/2022, 12/16/2022, 3/16/2023 and 6/16/2023.

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August 02, 2021 Filed Aug 4, 2021 16:37 UTC Upland Software, Inc. UPLD · Entity 7891 GrantCommon Stock 6,051 $0.00 $0.00
Disclosure

SEC source: 0001458635-21-000004 · wf-form4_162810941063112.xml · nonDerivative · entry 1

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 60,791

F1 · shares: Represents restricted stock units vesting in 4 equal installments on each of 9/16/2021, 12/16/2021, 3/16/2022 and 6/16/2022.

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March 01, 2021 Filed Mar 3, 2021 16:07 UTC Upland Software, Inc. UPLD · Entity 7891 SaleCommon Stock 10,000 $50.17 $501,653.00
Disclosure

SEC source: 0001458635-21-000002 · wf-form4_161480564745544.xml · nonDerivative · entry 3

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · Roth IRA

Disclosed balance after: 0

F1 · kind: Shares were sold pursuant to shareholder's 10b5-1 trading plan.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $50.00 to $50.31, inclusive. The reporting person undertakes to provide to Upland Software, Inc., any security holder of Upland Software, Inc., or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote to this Form 4.

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March 01, 2021 Filed Mar 3, 2021 16:07 UTC Upland Software, Inc. UPLD · Entity 7891 SaleCommon Stock 100 $51.05 $5,105.00
Disclosure

SEC source: 0001458635-21-000002 · wf-form4_161480564745544.xml · nonDerivative · entry 2

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 54,740

F1 · kind: Shares were sold pursuant to shareholder's 10b5-1 trading plan.

Read SEC document
March 01, 2021 Filed Mar 3, 2021 16:07 UTC Upland Software, Inc. UPLD · Entity 7891 SaleCommon Stock 9,900 $50.04 $495,410.85
Disclosure

SEC source: 0001458635-21-000002 · wf-form4_161480564745544.xml · nonDerivative · entry 1

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 54,840

F1 · kind: Shares were sold pursuant to shareholder's 10b5-1 trading plan.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $50.00 to $50.375, inclusive. The reporting person undertakes to provide to Upland Software, Inc., any security holder of Upland Software, Inc., or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote to this Form 4.

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August 17, 2020 Filed Aug 18, 2020 09:06 UTC Upland Software, Inc. UPLD · Entity 7891 PurchaseCommon Stock 10,000 $33.72 $337,237.00
Disclosure

SEC source: 0001458635-20-000006 · wf-form4_159775595358873.xml · nonDerivative · entry 2

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: Not disclosed

Ownership: Indirect · Roth IRA

Disclosed balance after: 10,000

F1 · price: The price reported is a weighted average price. These shares were purchased in multiple transactions at prices ranging from $33.588 to $33.8899, inclusive. The reporting person undertakes to provide to Upland Software, Inc., any security holder of Upland Software, Inc., or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares purchased at each separate price within the ranges set forth in this footnote to this Form 4.

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August 03, 2020 Filed Aug 5, 2020 16:08 UTC Upland Software, Inc. UPLD · Entity 7891 GrantCommon Stock 4,567 $0.00 $0.00
Disclosure

SEC source: 0001458635-20-000004 · wf-form4_159665809127695.xml · nonDerivative · entry 1

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 64,740

F1 · shares: Represents restricted stock units vesting in four quarterly installments beginning on the three-month anniversary of the Vesting Commencement date, provided the participant continues to serves as a director through such dates.

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January 13, 2020 Filed Feb 6, 2020 16:28 UTC Upland Software, Inc. UPLD · Entity 7891 GiftCommon Stock 300 $0.00 $0.00
Disclosure

SEC source: 0001458635-20-000002 · wf-form5_158102446976334.xml · nonDerivative · entry 2

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 60,173

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December 31, 2019 Filed Feb 6, 2020 16:28 UTC Upland Software, Inc. UPLD · Entity 7891 GiftCommon Stock 300 $0.00 $0.00
Disclosure

SEC source: 0001458635-20-000002 · wf-form5_158102446976334.xml · nonDerivative · entry 1

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 60,473

Read SEC document
August 23, 2019 Filed Aug 26, 2019 16:10 UTC Upland Software, Inc. UPLD · Entity 7891 SaleCommon Stock 5,000 $42.74 $213,710.50
Disclosure

SEC source: 0001458635-19-000008 · wf-form4_156685021490102.xml · nonDerivative · entry 2

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 60,773

F2 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $42.4251 to $43.055, inclusive. The reporting person undertakes to provide to Upland Software, Inc., any security holder of Upland Software, Inc., or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote to this Form 4.

Read SEC document
August 22, 2019 Filed Aug 26, 2019 16:10 UTC Upland Software, Inc. UPLD · Entity 7891 SaleCommon Stock 15,000 $42.83 $642,514.50
Disclosure

SEC source: 0001458635-19-000008 · wf-form4_156685021490102.xml · nonDerivative · entry 1

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 65,773

F1 · price: The price reported is a weighted average price. These shares were sold in multiple transactions at prices ranging from $42.7426 to $42.90, inclusive. The reporting person undertakes to provide to Upland Software, Inc., any security holder of Upland Software, Inc., or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote to this Form 4.

Read SEC document
August 05, 2019 Filed Aug 7, 2019 16:23 UTC Upland Software, Inc. UPLD · Entity 7891 GrantCommon Stock 1,188 $0.00 $0.00
Disclosure

SEC source: 0001458635-19-000006 · wf-form4_156520940177821.xml · nonDerivative · entry 1

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 80,773

F1 · shares: Represents restricted stock units vesting as follows: 297 shares on each of 9/16/19, 12/16/2019, 3/16/20 and 6/16/20.

Read SEC document
August 06, 2018 Filed Aug 8, 2018 16:34 UTC Upland Software, Inc. UPLD · Entity 7891 GrantCommon Stock · Derivative 4,378 $0.00 Strike: $33.39 $0.00
Disclosure

SEC source: 0001458635-18-000004 · wf-form4_153376044524371.xml · derivative · entry 1

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 4,378

Underlying: Common Stock · 4,378 shares

Expires 2028-08-06

F1 · derivative.exercise_date: Options vest and become exercisable as to 25% of shares on each of 9/16/19, 12/16/18, 3/16/19 and 6/16/19.

Read SEC document
August 06, 2018 Filed Aug 30, 2018 16:15 UTC Amendment Upland Software, Inc. UPLD · Entity 7891 GrantStock Option (right to buy) · Derivative 4,378 $0.00 Strike: $33.39 $0.00
Disclosure

SEC source: 0001458635-18-000006 · wf-form4a_153566012496871.xml · derivative · entry 1

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 4,378

Underlying: Common Stock · 4,378 shares

Expires 2028-08-06

F1 · security: Form was amended to correct the Title of Derivative Security.

F2 · derivative.exercise_date: Options vest and become exercisable as to 25% of shares on each of 9/16/19, 12/16/18, 3/16/19 and 6/16/19.

Read SEC document
July 16, 2018 Filed Jul 18, 2018 18:34 UTC Upland Software, Inc. UPLD · Entity 7891 SaleCommon Stock 20,000 $34.96 $699,160.00
Disclosure

SEC source: 0001628280-18-009343 · wf-form4_153195324606644.xml · nonDerivative · entry 1

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 103,500

F1 · kind: Shares were sold pursuant to shareholder's 10b5-1 trading plan adopted by owner on May 14, 2018, with an effective date of July 15, 2018.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $34.87 to $35.66, inclusive. The reporting person undertakes to provide to Upland Software, Inc., any security holder of Upland Software, Inc., or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote to this Form 4.

Read SEC document
June 18, 2018 Filed Jun 19, 2018 17:28 UTC Upland Software, Inc. UPLD · Entity 7891 SaleCommon Stock 4,979 $36.06 $179,558.67
Disclosure

SEC source: 0001458635-18-000002 · wf-form4_152944368856600.xml · nonDerivative · entry 2

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 123,500

F1 · kind: Shares were sold pursuant to shareholder's 10b5-1 trading plan adopted by owner on May 14, 2018, with an effective date of June 15, 2018.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $35.185 to $36.82, inclusive. The reporting person undertakes to provide to Upland Software, Inc., any security holder of Upland Software, Inc., or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote to this Form 4.

Read SEC document
June 15, 2018 Filed Jun 19, 2018 17:28 UTC Upland Software, Inc. UPLD · Entity 7891 SaleCommon Stock 35,021 $35.21 $1,233,145.44
Disclosure

SEC source: 0001458635-18-000002 · wf-form4_152944368856600.xml · nonDerivative · entry 1

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 128,479

F1 · kind: Shares were sold pursuant to shareholder's 10b5-1 trading plan adopted by owner on May 14, 2018, with an effective date of June 15, 2018.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $35.00 to $35.39, inclusive. The reporting person undertakes to provide to Upland Software, Inc., any security holder of Upland Software, Inc., or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote to this Form 4.

Read SEC document
September 15, 2017 Filed Sep 19, 2017 16:55 UTC Upland Software, Inc. UPLD · Entity 7891 SaleCommon Stock 25,000 $21.43 $535,750.00
Disclosure

SEC source: 0001458635-17-000006 · wf-form4_150585450391880.xml · nonDerivative · entry 1

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 138,500

F1 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $21.00 to $21.91, inclusive. The reporting person undertakes to provide to Upland Software, Inc., any security holder of Upland Software, Inc., or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range.

Read SEC document
August 08, 2017 Filed Oct 5, 2017 16:04 UTC Upland Software, Inc. UPLD · Entity 7891 GrantStock Option (right to buy) · Derivative 6,525 $0.00 Strike: $23.60 $0.00
Disclosure

SEC source: 0001458635-17-000008 · wf-form4_150723386246875.xml · derivative · entry 1

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 45,242

Underlying: Common Stock · 6,525 shares

Expires 2027-08-08

F1 · derivative.exercise_date: The option vests and becomes exercisable in twelve equal monthly installments commencing on June 16, 2017.

Read SEC document
November 16, 2016 Filed Nov 18, 2016 13:24 UTC Upland Software, Inc. UPLD · Entity 7891 PurchaseCommon Stock 10,000 $8.59 $85,900.00
Disclosure

SEC source: 0001458635-16-000006 · wf-form4_147949344334490.xml · nonDerivative · entry 1

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 163,500

F1 · price: The price reported in Column 4 is a weighted average price. These shares were bought in multiple transactions at prices ranging from $8.47 to $8.69, inclusive. The reporting person undertakes to provide to Upland Software, Inc., any security holder of Upland Software, Inc., or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares bought at each separate price within the range set forth in this footnote (1).

Read SEC document
August 08, 2016 Filed Aug 30, 2018 16:09 UTC Amendment Upland Software, Inc. UPLD · Entity 7891 GrantStock Option (right to buy) · Derivative 38,717 $0.00 Strike: $7.74 $0.00
Disclosure

SEC source: 0001458635-18-000005 · wf-form4a_153565975131387.xml · derivative · entry 1

MAY DAVID · CIK 0001458635 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 38,717

Underlying: Common Stock · 38,717 shares

Expires 2026-08-08

F1 · security: Form was amended to correct the Title of Derivative Security.

F2 · derivative.exercise_date: The option vests and becomes exercisable in twelve equal monthly installments commencing on June 17, 2016.

Read SEC document

Value uses the disclosed total when available, otherwise shares × reported transaction price. It is not an estimate of exercise cash cost or investment performance.