13D Filing: ESW Capital, LLC and Upland Software Inc. (UPLD)

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This Amendment No. 8 to Schedule 13D amends and supplements the Schedule 13D originally filed on
June 23, 2015 (the Original Schedule 13D), as amended and supplemented by Amendment No. 1 to Schedule 13D filed on July 22, 2015 (Amendment No. 1), Amendment No. 2 to Schedule 13D filed on
August 24, 2015 (Amendment No. 2), Amendment No. 3 to Schedule 13D filed on December 22, 2015 (Amendment No. 3), Amendment No. 4 to Schedule 13D filed on January 19, 2016 (Amendment
No. 4), Amendment No. 5 to Schedule 13D filed on March 17, 2016 (Amendment No. 5) , Amendment No. 6 to Schedule 13D filed on March 24, 2016, and Amendment No. 7 to Schedule 13D filed on
June 8, 2017 relating to the common stock, $0.0001 par value per share (the Shares), of Upland Software, Inc., a Delaware corporation (the Issuer). The purpose of this Amendment No. 8 to Schedule 13D is to report
that on June 23, Wave Systems Corp., a wholly-owned subsidiary of ESW Capital, LLC, sold 561,712 shares in the open market.

Unless otherwise defined
or modified below, capitalized terms used in this Amendment No. 8 to Schedule 13D shall have the meaning ascribed to them in the Original Schedule 13D, Amendment No. 1, Amendment No. 2, Amendment No. 3, Amendment No. 4,
Amendment No. 5, Amendment No. 6 and Amendment No. 7.

All disclosure for items contained in the Original Schedule 13D, Amendment
No. 1, Amendment No. 2, Amendment No. 3, Amendment No. 4, Amendment No. 5, Amendment No. 6 and Amendment No. 7 where no new information is provided for such item in this Amendment No. 8 to Schedule 13D is
incorporated herein by this reference.

ITEM 5. INTEREST IN SECURITIES OF THE ISSUER.

(a) and (b) As of June 23, 2017, ESW may be deemed to beneficially own 5,117,185 Shares, representing approximately 27.8% of the 18,437,943 shares of
the Issuers common stock outstanding on May 5, 2017 as reported in the Issuers Quarterly Report on Form 10-Q for the period ended March 31, 2017, filed with the Securities and Exchange Commission on May 12, 2017. The
5,117,185 shares consist of 2,313,611 Shares held directly by Wave (the Wave Shares), 1,803,574 Shares held directly by Acorn (the Acorn Shares) and 1,000,000 Shares held directly by EPM Live (the EPM
Live Shares
). ESW may be deemed to have sole voting and dispositive power with respect to the Acorn Shares, the EPM Live Shares and the Wave Shares.

As of June 23, 2017, Acorn may be deemed to beneficially own 1,803,574 Shares held directly by it, representing approximately 9.8% of the 18,437,943
shares of the Issuers common stock outstanding on May 5, 2017 as reported in the Issuers Quarterly Report on Form 10-Q for the period ended March 31, 2017, filed with the Securities and Exchange Commission on May 12, 2017.
Acorn has sole voting, investment and dispositive power with respect to the Acorn Shares.

As of June 23, 2017, Liemandt may be deemed to
beneficially own the 5,117,185 Shares that consist of the Wave Shares, the Acorn Shares and the EPM Live Shares, representing approximately 27.8% of the 18,437,943 shares of the Issuers common stock outstanding on May 5, 2017 as reported
in the Issuers Quarterly Report on Form 10-Q for the period ended March 31, 2017, filed with the Securities and Exchange Commission on May 12, 2017. Liemandt may be deemed to have sole voting, investment and dispositive power with
respect to the Wave Shares, the Acorn Shares and the EPM Live Shares.

As of June 23, 2017, EPM Live may be deemed to beneficially own 1,000,000
Shares held directly by it, representing approximately 5.4% of the 18,437,943 shares of the Issuers common stock outstanding on May 5, 2017 as reported in the Issuers Quarterly Report on Form 10-Q for the period ended
March 31, 2017, filed with the Securities and Exchange Commission on May 12, 2017. EPM Live has sole voting, investment and dispositive power with respect to the EPM Live Shares.

As of June 23, 2017, Wave may be deemed to beneficially own 2,313,611 Shares held directly by it, representing approximately 12.5% of the 18,437,943
shares of the Issuers common stock outstanding on May 5, 2017 as

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