Upland Software, Inc. 10-Q

Item 2. Unregistered Sales of Equity Securities and Use of Proceeds Issuer Purchases of Equity Securities On August 15, 2025, the Board of Directors authorized a stock repurchase program (the “2025 Share Repurchase Plan” as defined in Note 10. Stockholders' Deficit ) in the aggregate amount of up to $10,000,000 (inclusive of any taxes payable as a result of such repurchase). The authorization does not have a specified expiration date. Accordingly, unless terminated earlier by resolution of the Board, the 2025 Share Repurchase Plan will expire when the Company has repurchased all shares authorized for repurchase thereunder. The Company is not obligated to acquire any particular amount of Common Stock and may modify or suspend the repurchases at any time in the Company’s discretion. The following table provides information about purchases of equity securities that are registered by the Company pursuant to Section 12 of the Exchange Act during the three months ended September 30, 2025. Period Total number of shares purchased Average price paid per share (1) Total number of shares purchased as part of the publicly announced plan Maximum approximate dollar value of shares that may yet be purchased under the plan 7/1/2025 -7/31/2025 — — — — 8/1/2025 - 8/31/2025 5,597 $ 2.73 5,597 $ 9,984,538 9/1/2025 - 9/30/2025 (2) 142,776 $ 2.41 50,000 $ 9,862,718 148,373 55,597 (1) Average price paid per share excludes commission costs and excise taxes associated with the above mentioned repurchases. (2) The total number of shares repurchased includes 92,776 shares withheld from employees to satisfy the statutory withholding tax liability upon the vesting of share-based awards.