X0407 4 2023-06-16 0001505155 Upland Software, Inc. UPLD 0001094792 MCDONALD JOHN T 401 CONGRESS AVE., SUITE 1850 AUSTIN TX 78701 true true false false CEO false Common Stock 2023-06-16 4 F false 11650 3.53 D 1655048 D Common Stock 263738 I By National Financial Services as Cust FBO J McDonald RRA 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. 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. /s/ Kin Gill, as attorney-in-fact for Mr. McDonald 2023-06-20