X0206 3 2014-11-05 0 0001505155 Upland Software, Inc. UPLD 0001094792 MCDONALD JOHN T 401 CONGRESS AVE., STE 1850 AUSTIN TX 78701 1 1 1 0 CEO Common Stock 1312005 D Series A Preferred Stock Common Stock 373911 D Series B Preferred Stock Common Stock 11200 D Series B Preferred Stock Common Stock 163961 I By MLPF&S as Cust. FBO J. McDonald IRA Series C Preferred Stock Common Stock 79777 I By MLPF&S as Cust. FBO J. McDonald IRA Includes 171,040 shares subject to repurchase by the company lapsing on 5/9/2018. The Series A Preferred Stock is convertible into Common Stock on a one-for-one basis at any time and has no expiration date. The Series A Preferred Stock will automatically convert into Common Stock immediately prior to the closing of the Issuer's initial public offering. The Series B Preferred Stock is convertible into Common Stock on a one-for-one basis at any time and has no expiration date. The Series B Preferred Stock will automatically convert into Common Stock immediately prior to the closing of the Issuer's initial public offering. The Series C Preferred Stock is convertible into Common Stock on a one-for-one basis at any time and has no expiration date. The Series C Preferred Stock will automatically convert into Common Stock immediately prior to the closing of the Issuer's initial public offering. /s/ Robert Housley, Attorney-in-Fact 2014-11-05