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

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 13D

(Rule 13d-102)

INFORMATION INCLUDED IN STATEMENTS FILED PURSUANT

TO RULE 13d-1(a) AND AMENDMENTS THERETO FILED PURSUANT TO

RULE 13d-2(a)

(Amendment
No. 8)*

UPLAND SOFTWARE, INC.

(Name of Issuer)

COMMON
STOCK, $0.0001 PAR VALUE PER SHARE

(Title of Class of Securities)

91544A109

(CUSIP Number)

ESW CAPITAL, LLC

401 CONGRESS AVENUE

SUITE 2650

AUSTIN, TX
78701

(512) 524-6149

(Name, Address and Telephone Number of Person Authorized to Receive Notices and Communications)

June 23, 2017

(Date
of Event Which Requires Filing of This Statement)

If the filing person has previously filed a statement on Schedule 13G to report the acquisition that is the subject of this Schedule 13D, and is filing
this schedule because of §§ 240.13d-1(e), 240.13d-1(f) or 240.13d-1(g), check the following box.  ☒

Note: Schedules filed in paper format shall
include a signed original and five copies of the schedule, including all exhibits. See §240.13d-7 for other parties to whom copies are to be sent.

The information required on the remainder of this cover page shall not be
deemed to be filed for the purpose of section 18 of the Securities Exchange Act of 1934 (Act) or otherwise subject to the liabilities of that section of the Act but shall be subject to all other provisions of the Act
(however, see the Notes).

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

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. Wave has sole
voting, investment and dispositive power with respect to the Wave Shares.

(c) On June 23, 2017, Wave sold 561,712 shares at the price per share of
$22.6845 per share (inclusive of brokerage commissions). Except for such transaction, no Reporting Person has effected any transaction in the Shares in the 60 days prior to the filing of this Amendment No. 8.

(d) Except as set forth in this Schedule 13D, to the knowledge of the Reporting Persons, no person had the right to receive or the power to direct the receipt
of dividends from, or the proceeds from the sale of, securities covered by this Schedule 13D.

(e) Not applicable.

ITEM 7. MATERIAL TO BE FILED AS EXHIBITS.

SIGNATURES

After reasonable inquiry and to the best of its knowledge and belief, the undersigned certifies that the information set forth in this Statement is true,
complete and correct.

Dated: June 27, 2017

Exhibit A

Joint Filing Agreement

In accordance with Rule
13d-1(f) under the Securities and Exchange Act of 1934, the persons or entities named below agree to the joint filing on behalf of each of them of a statement on Schedule 13D (including amendments thereto) with respect to the Shares of the Issuer
and further agree that this joint filing agreement be included as an exhibit to this Schedule 13D. In evidence thereof, the undersigned, being duly authorized, have executed this Joint Filing Agreement as of June 27, 2017.