UPLD / Upland Software, Inc. - Pengajuan SECLaporan Tahunan, Pernyataan Proksi

Upland Software, Inc.
US ˙ NasdaqGM ˙ US91544A1097

Mga Batayang Estadistika
LEI 549300NS277POYJ63W89
CIK 1505155
SEC Filings
All companies that sell securities in the United States must register with the Securities and Exchange Commission (SEC) and file reports on a regular basis. These reports include company annual reports (10K, 10Q), news updates (8K), investor presentations (found in 8Ks), insider trades (form 4), ownership reports (13D, and 13G), and reports related to the specific securities sold, such as registration statements and prospectus. This page shows recent SEC filings related to Upland Software, Inc.
SEC Filings (Chronological Order)
Halaman ini menyediakan daftar lengkap dan kronologis dari Pengajuan SEC, tidak termasuk pengajuan kepemilikan yang kami sediakan di tempat lain.
August 18, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 August 15, 2025 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 August 15, 2025 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

July 31, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 July 31, 2025 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 July 31, 2025 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

July 31, 2025 EX-99.1

Upland Software Reports Second Quarter 2025 Financial Results

EXHIBIT 99.1 Upland Software Reports Second Quarter 2025 Financial Results July 31, 2025, 09:00 AM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD), a leader in AI-powered knowledge and content management software, today announced its financial and operating results for the second quarter 2025 and issued guidance for its third quarter and full year of 2025.

July 31, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2025 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36720 UPLA

July 31, 2025 10-K/A

F UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No. 1) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 ☐ TRANSITION RE

F UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No. 1) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission File Number 001-36720 Upland Software, Inc. (Exact name of r

July 28, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 July 25, 2025 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 July 25, 2025 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

July 28, 2025 EX-99.1

Upland Software Announces the Successful Completion of Debt Refinancing

EXHIBIT 99.1 Upland Software Announces the Successful Completion of Debt Refinancing July 28, 2025 AUSTIN, Texas- Upland Software, Inc. (Nasdaq: UPLD) (the “Company” or “Upland Software”), a leader in AI-powered knowledge and content management software, today announced that it has entered into an agreement with private credit direct lender Sound Point Capital to refinance its existing debt with a

July 28, 2025 EX-10.1

Credit Agreement, dated as of July 25, 2025, by and among Upland Software, Inc., the subsidiary guarantors party thereto, Sound Point Capital, as administrative agent, and the lenders party thereto.

Exhibit 10.1 CREDIT AGREEMENT dated as of July 25, 2025 among UPLAND SOFTWARE, INC., as the Borrower the Lenders party hereto, and SOUND POINT AGENCY LLC, as Administrative Agent SOUND POINT AGENCY LLC, as Sole Lead Arranger and Sole Book Runner LEGALUSE # 188054825.13 TABLE OF CONTENTS Page ARTICLE I DEFINITIONS 1 Section 1.01 Defined Terms 1 Section 1.02 Classification of Loans and Borrowings 69

July 14, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 July 11, 2025 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 July 11, 2025 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

June 4, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 June 4, 2025 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC. (

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 June 4, 2025 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

May 12, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 May 12, 2025 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC. (

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 May 12, 2025 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

May 12, 2025 EX-99.1

Upland Software Reports First Quarter 2025 Financial Results

EXHIBIT 99.1 Upland Software Reports First Quarter 2025 Financial Results May 12, 2025, 09:05 AM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based tools for digital transformation, today announced financial and operating results for the first quarter 2025 and issued guidance for its second quarter and full year of 2025. First Quarter

May 12, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2025 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36720 UPL

April 21, 2025 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) o Defin

April 21, 2025 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ý Defin

April 4, 2025 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 April 1, 2025 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

March 12, 2025 EX-99.1

Upland Software Reports Fourth Quarter 2024 Financial Results

EXHIBIT 99.1 Upland Software Reports Fourth Quarter 2024 Financial Results March 12, 2025, 9:05 a.m. Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based tools for digital transformation, today announced financial and operating results for the fourth quarter 2024 and issued guidance for its first quarter and full year of 2025. Fourth Qu

March 12, 2025 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 March 12, 2025 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

March 12, 2025 EX-21.1

List of subsidiaries of Upland Software, Inc.

Exhibit 21.1 List of Subsidiaries of Upland Software, Inc. as of December 31, 2024 Upland Software Inc. Upland Software UK Limited Upland Software Australia Pty Ltd Upland Software India Private Limited Upland Software Ireland Limited Upland Software Interfax Ireland Limited Upland Software Inc. / Logiciels Upland Inc. Return Fax 2000 Ltd. Adestra Pty Limited BlueVenn Group Limited BlueVenn Group

March 12, 2025 EX-10.38

Executive Employment Agreement between Registrant and Matt Breslin, dated February 6, 2024

Executive Officer Employment Agreement for Matt Breslin UPLAND SOFTWARE, INC. EXECUTIVE EMPLOYMENT AGREEMENT This Executive Employment Agreement (the “Agreement”) is entered into effective as of February 6, 2024 (the “Effective Date”) by and between Upland Software, Inc., a Delaware corporation (the “Company”), and Matt Breslin (“Executive”). RECITALS WHEREAS, the Company and Executive desire to m

March 12, 2025 EX-19

Insider Trading Policy

UPLAND SOFTWARE, INC. INSIDER TRADING POLICY and Guidelines with Respect to Certain Transactions in Securities (Amended by the Board of Directors: October 29, 2024) TABLE OF CONTENTS Page INTRODUCTION 1 Legal Prohibitions on Insider Trading 1 Detection and Prosecution of Insider Trading 1 Penalties for Violation of Insider Trading Llaws and this Policy 1 General Counsel 2 Reporting Violations 2 Pe

March 12, 2025 EX-10.34

Amendment #1 to Employment Agreement between the Registrant and Karen Cummings, dated January 30, 2024

EXECUTIVE OFFICER AMENDED AGREEMENT FOR KAREN CUMMINGS Amendment # 1 to UPLAND SOFTWARE, INC.

March 12, 2025 EX-10.33

Employment Agreement between the Registrant and Karen Cummings, dated December 16, 2022

UPLAND SOFTWARE, INC. EXECUTIVE EMPLOYMENT AGREEMENT This Executive Employment Agreement (the “Agreement”) is entered into effective as of December 16, 2022 (the “Effective Date”) by and between Upland Software, Inc., a Delaware corporation (the “Company”), and Karen Cummings (“Executive”). RECITALS WHEREAS, the Company and Executive desire to memorialize the terms of employment of Executive as of

March 12, 2025 EX-10.37

Executive Employment Agreement between Registrant and Oliver Yates, dated January 9, 2023

UPLAND SOFTWARE, INC. EXECUTIVE EMPLOYMENT AGREEMENT This Executive Employment Agreement (the “Agreement”) is entered into effective as of January 9, 2023 (the “Effective Date”) by and between Upland Software, Inc., a Delaware corporation (the “Company”), and Oliver RM Yates (“Executive”). RECITALS WHEREAS, the Company and Executive desire to memorialize the terms of employment of Executive as of

March 12, 2025 EX-10.32

Amendment #3 to Employment Agreement between the Registrant and John T. McDonald, dated January 30, 2024

EXECUTIVE OFFICER AMENDED AGREEMENT FOR JOHN MCDONALD Amendment # 3 to UPLAND SOFTWARE, INC.

March 12, 2025 10-K

F UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 ☐ TRANSITION REPORT PURSUANT TO SEC

F UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission File Number 001-36720 Upland Software, Inc. (Exact name of registrant as specifi

March 3, 2025 EX-3.1

Amendment to the Second Amended and Restated Bylaws of Upland Software, Inc.

Exhibit 3.1 AMENDMENT TO THE SECOND AMENDED AND RESTATED BYLAWS OF UPLAND SOFTWARE, INC. Pursuant to Article VI of the Amended and Restated Certificate of Incorporation, as amended, of Upland Software, Inc., a Delaware corporation (the “Corporation”), Article II, Section 2.9 of the Second Amended and Restated Bylaws (as amended heretofore, the “Bylaws”) of the Corporation, and Section 109 of the G

March 3, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 February 25, 2025 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 February 25, 2025 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

February 14, 2025 EX-99

JOINT FILING AGREEMENT

Exhibit A JOINT FILING AGREEMENT The undersigned agree that this Schedule 13G dated February 14, 2025 relating to the Common stock, $0.

February 14, 2025 EX-99

CONTROL PERSON IDENTIFICATION

Exhibit B CONTROL PERSON IDENTIFICATION CastleKnight Master Fund LP is the relevant entity for which Aaron Weitman may be considered a control person.

January 31, 2025 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 January 31, 2025 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

January 30, 2025 EX-99.1

JOINT FILING AGREEMENT PURSUANT TO RULE 13d-1(k)

EX-99.1 2 tm254825d1ex99-1.htm EXHIBIT 99.1 Exhibit 99.1 JOINT FILING AGREEMENT PURSUANT TO RULE 13d-1(k) Each undersigned acknowledges and agrees that the foregoing Schedule 13G is filed on behalf of the undersigned and that all subsequent amendments to this Schedule 13G shall be filed on behalf of each undersigned without the necessity of filing additional joint filing agreements. Each undersign

November 7, 2024 10-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No. 1) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 ☐ TRANSITION REPO

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No. 1) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission File Number 001-36720 Upland Software, Inc. (Exact name of reg

November 7, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36720

November 7, 2024 EX-99.1

Upland Software Reports Third Quarter 2024 Financial Results

EXHIBIT 99.1 Upland Software Reports Third Quarter 2024 Financial Results November 7, 2024, 04:01 PM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based tools for digital transformation, today announced financial and operating results for the third quarter 2024 and issued guidance for its fourth quarter and full year of 2024. Third Qua

November 7, 2024 10-Q/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q/A (Amendment #1)

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q/A (Amendment #1) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file num

November 7, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 November 7, 2024 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

November 7, 2024 10-Q/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q/A (Amendment No. 1)

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q/A (Amendment No. 1) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file n

August 8, 2024 SC 13G

UPLD / Upland Software, Inc. / CastleKnight Master Fund LP Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No.

August 1, 2024 EX-99.1

Upland Software Reports Second Quarter 2024 Financial Results

EXHIBIT 99.1 Upland Software Reports Second Quarter 2024 Financial Results August 1, 2024, 04:01 PM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based tools for digital transformation, today announced financial and operating results for the second quarter 2024 and issued guidance for its third quarter and full year of 2024. Second Qua

August 1, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36720 UPLA

August 1, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 August 1, 2024 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

June 17, 2024 SC 13D/A

UPLD / Upland Software, Inc. / ULYSSES AGGREGATOR, LP - AMENDMENT NO. 3 TO SCHEDULE 13D Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 3)* UPLAND SOFTWARE, INC. (Name of Issuer) Common Stock, par value $0.0001 per share (Title of Class of Securities) 91544A109 (CUSIP Number) David Chung Ulysses Aggregator, LP c/o HGGC, LLC 1950 University Avenue, Suite 350 Palo Alto, CA 94303 Tel: (650) 321

June 5, 2024 EX-4.1

Upland Software, Inc. 2024 Omnibus Incentive Plan.

Upland Software, Inc. 2024 Omnibus Incentive Plan UPLAND SOFTWARE, INC. 2024 OMNIBUS INCENTIVE PLAN 1.Purposes of the Plan. The purposes of the Plan are to attract and retain the best available personnel, to provide additional incentives to Employees, Directors and Consultants and to promote the success of the Company. 2.Definitions. The following definitions shall apply as used herein and in the

June 5, 2024 EX-10.3

Form of Upland Software, Inc. 2024 Omnibus Incentive Plan Restricted Stock Unit Award Agreement.

UPLAND SOFTWARE, INC. 2024 OMNIBUS INCENTIVE PLAN RESTRICTED STOCK UNIT AGREEMENT Unless otherwise defined herein, the terms defined in the Upland Software, Inc. 2024 Omnibus Incentive Plan (the “Plan”) will have the same defined meanings in this Restricted Stock Unit Agreement (the “Award Agreement”), which includes the Notice of Restricted Stock Unit Grant (the “Notice of Grant”), Terms and Cond

June 5, 2024 EX-10.1

Tax Benefit Preservation Plan, dated as June 5, 2024, by and between Upland Software, Inc. and Broadridge Corporate Issuer Solutions, LLC, as rights agent.

TAX BENEFIT PRESERVATION PLAN by and between Upland Software, Inc. and Broadridge Corporate Issuer Solutions, LLC as Rights Agent Dated as of June 5, 2024 TABLE OF CONTENTS Page 1......... Certain Definitions................................................................................. 1 2......... Appointment of Rights Agent................................................................ 7 3..

June 5, 2024 EX-FILING FEES

Filing Fee Table.

Exhibit 107 Calculation of Filing Fee Table Form S-8 (Form Type) Upland Software, Inc.

June 5, 2024 8-A12B

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) OR 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 UPLAND SOFTWARE, INC. (Exact name of registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) OR 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 UPLAND SOFTWARE, INC.

June 5, 2024 S-8

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 UPLAND SOFTWARE, INC. (Exact name of registrant as specified in its charter)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 UPLAND SOFTWARE, INC.

June 5, 2024 EX-10.1

Upland Software, Inc. 2024 Omnibus Incentive Plan (which is incorporated herein by reference to Exhibit 10.1 to the Registrant’s Current Report on Form 8-K filed on June 5, 2024).

Upland Software, Inc. 2024 Omnibus Incentive Plan UPLAND SOFTWARE, INC. 2024 OMNIBUS INCENTIVE PLAN 1.Purposes of the Plan. The purposes of the Plan are to attract and retain the best available personnel, to provide additional incentives to Employees, Directors and Consultants and to promote the success of the Company. 2.Definitions. The following definitions shall apply as used herein and in the

June 5, 2024 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Entry into a Material Definitive Agreement, Material Modification to Rights of Security Holders, Financial Statements and Exhibits, Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 June 5, 2024 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

June 5, 2024 EX-10.2

Form of Upland Software, Inc. 2024 Omnibus Incentive Plan Performance Unit Award Agreement.

UPLAND SOFTWARE, INC. 2024 OMNIBUS INCENTIVE PLAN PERFORMANCE UNIT AGREEMENT Unless otherwise defined herein, the terms defined in the Upland Software, Inc. 2024 Omnibus Incentive Plan (the “Plan”) will have the same defined meanings in this Performance Unit Agreement (the “Award Agreement”), which includes the Notice of Performance Unit Grant (the “Notice of Grant”) and the Terms and Conditions o

May 30, 2024 15-12G

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 15 CERTIFICATION AND NOTICE OF TERMINATION OF REGISTRATION UNDER SECTION 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 OR SUSPENSION OF DUTY TO FILE REPORTS UNDER SECTIONS 13

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 15 CERTIFICATION AND NOTICE OF TERMINATION OF REGISTRATION UNDER SECTION 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 OR SUSPENSION OF DUTY TO FILE REPORTS UNDER SECTIONS 13 AND 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934. Commission File Number 001-36720 UPLAND SOFTWARE, INC. (Exact name of registrant as specified in it

May 2, 2024 EX-10.1

Amendment # 1 to Employment Agreement between the Registrant and Karen Cummings, dated January

EXECUTIVE OFFICER AMENDED AGREEMENT FOR KAREN CUMMINGS Amendment # 1 to UPLAND SOFTWARE, INC.

May 2, 2024 EX-10.2

Amendment # 3 to Employment Agreement between the Registrant and John T. McDonald, dated January

EXECUTIVE OFFICER AMENDED AGREEMENT FOR JOHN MCDONALD Amendment # 3 to UPLAND SOFTWARE, INC.

May 2, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 May 2, 2024 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC. (E

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 May 2, 2024 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

May 2, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36720 UPL

May 2, 2024 EX-99.1

Upland Software Reports First Quarter 2024 Financial Results

EXHIBIT 99.1 Upland Software Reports First Quarter 2024 Financial Results May 2, 2024, 04:01 PM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based tools for digital transformation, today announced financial and operating results for the first quarter 2024 and issued guidance for its second quarter and full year of 2024. First Quarter

April 26, 2024 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) o Defin

April 26, 2024 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ý Defin

April 16, 2024 PRE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: ý Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) o Defin

February 27, 2024 SC 13D/A

UPLD / Upland Software, Inc. / ULYSSES AGGREGATOR, LP - AMENDMENT NO. 2 TO SCHEDULE 13D Activist Investment

SC 13D/A 1 ea0200789-13da2ulyssesuplan.htm AMENDMENT NO. 2 TO SCHEDULE 13D UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 2)* UPLAND SOFTWARE, INC. (Name of Issuer) Common Stock, par value $0.0001 per share (Title of Class of Securities) 91544A109 (CUSIP Number) David Chung Ulysses Aggregator, LP c/o HGG

February 22, 2024 EX-21.1

List of subsidiaries of Upland Software, Inc.

Exhibit 21.1 List of Subsidiaries of Upland Software, Inc. as of December 31, 2023 Upland Software Inc. Upland Software UK Limited Upland Software Australia Pty Ltd Upland Software India Private Limited Upland Software Ireland Limited Return Fax 2000 Ltd. Rapide Communications Ltd. Adestra Limited Adestra Pty Limited Altify, Ltd. BlueVenn Group Limited BlueVenn Group Holdings Limited BlueDeveloper

February 22, 2024 EX-4.1

Description of Capital Stock

Exhibit 4.1 DESCRIPTION OF SECURITIES REGISTERED UNDER SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 This section describes the general terms and provisions of the shares of the common stock, par value of $0.0001 per share (the “Common Stock”) of Upland Software, Inc., a Delaware corporation (the “Company,” “we,” “our”), and the preferred stock purchase rights (a “Right”) to purchase one one-t

February 22, 2024 EX-99.1

Upland Software Reports Fourth Quarter 2023 Financial Results

EXHIBIT 99.1 Upland Software Reports Fourth Quarter 2023 Financial Results February 22, 2024, 04:01 PM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based tools for digital transformation, today announced financial and operating results for the fourth quarter 2023 and issued guidance for its first quarter and full year of 2024. Fourth

February 22, 2024 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 ☐ TRANSITION REPORT PURSUANT TO SECTI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission File Number 001-36720 Upland Software, Inc. (Exact name of registrant as specified

February 22, 2024 EX-97.1

Policy relating to recovery of erroneously awarded compensation, as required by applicable listing standards adopted pursuant to 17 CFR 240.10D-1

UPLAND SOFTWARE, INC. COMPENSATION RECOUPMENT POLICY EFFECTIVE DATE: OCTOBER 2, 2023 In the event of any required accounting restatement of the financial statements of Upland Software, Inc. (the “Company”) due to the material noncompliance of the Company with any financial reporting requirement under the applicable U.S. federal securities laws, including any required accounting restatement to corr

February 22, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 February 22, 2024 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

February 13, 2024 SC 13G/A

UPLD / Upland Software, Inc. / VANGUARD GROUP INC - SCHEDULE 13G/A Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 1)* Name of issuer: Upland Software Inc Title of Class of Securities: Common Stock CUSIP Number: 91544A109 Date of Event Which Requires Filing of this Statement: December 29, 2023 Check the appropriate box to designate the rule pursuant to which this Schedule is filed: ☒

January 30, 2024 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 January 30, 2024 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

January 9, 2024 S-8

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 UPLAND SOFTWARE, INC. (Exact name of registrant as specified in its charter)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 UPLAND SOFTWARE, INC.

January 9, 2024 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Table Form S-8 (Form Type) Upland Software, Inc.

December 18, 2023 SC 13D/A

UPLD / Upland Software, Inc. / ULYSSES AGGREGATOR, LP - AMENDMENT NO. 1 TO SCHEDULE 13D Activist Investment

SC 13D/A 1 ea190165-13da1ulyssesupland.htm AMENDMENT NO. 1 TO SCHEDULE 13D UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 1)* UPLAND SOFTWARE, INC. (Name of Issuer) Common Stock, par value $0.0001 per share (Title of Class of Securities) 91544A109 (CUSIP Number) David Chung Ulysses Aggregator, LP c/o HGG

December 8, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 December 5, 2023 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, IN

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 December 5, 2023 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

November 2, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36720

November 2, 2023 EX-99

Upland Software Reports Third Quarter 2023 Financial Results

EXHIBIT 99.1 Upland Software Reports Third Quarter 2023 Financial Results November 2, 2023, 04:01 PM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based tools for digital transformation, today announced financial and operating results for the third quarter 2023 and issued guidance for its fourth quarter and full year of 2023. Third Qua

November 2, 2023 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 November 2, 2023 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

September 1, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 September 1, 2023 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 September 1, 2023 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

August 3, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36720 UPLA

August 3, 2023 EX-10.1

Employment Agreement between the Registrant and Dan Doman, dated November 1, 2022

UPLAND SOFTWARE, Inc. EXECUTIVE EMPLOYMENT AGREEMENT This Executive Employment Agreement (the “Agreement”) is entered into effective as of November 1, 2022 (the “Effective Date”) by and between Upland Software, Inc., a Delaware corporation (the “Company”), and Daniel Doman (“Executive”). RECITALS WHEREAS, the Company and Executive desire to memorialize the terms of employment of Executive as of th

August 3, 2023 EX-99.1

Upland Software Reports Second Quarter 2023 Financial Results

EXHIBIT 99.1 Upland Software Reports Second Quarter 2023 Financial Results August 3, 2023, 04:01 PM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based tools for digital transformation, today announced financial and operating results for the second quarter 2023 and issued guidance for its third quarter and full year of 2023. Second Qua

August 3, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 August 3, 2023 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 August 3, 2023 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

June 8, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 June 7, 2023 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC. (

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 June 7, 2023 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

June 8, 2023 EX-3.1

Certificate of Amendment to the Amended and Restated Certificate of Incorporation of Upland Software, Inc.

CERTIFICATE OF AMENDMENT TO THE AMENDED AND RESTATED CERTIFICATE OF INCORPORATION OF UPLAND SOFTWARE, INC.

May 25, 2023 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. 1 )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. 1 ) Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) o Def

May 9, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36720 UPL

May 4, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 May 4, 2023 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC. (E

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 May 4, 2023 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

May 4, 2023 EX-99.1

Upland Software Reports First Quarter 2023 Financial Results Company Beats Q1 Guidance and Reaffirms Full Year 2023 Guidance

EXHIBIT 99.1 Upland Software Reports First Quarter 2023 Financial Results Company Beats Q1 Guidance and Reaffirms Full Year 2023 Guidance May 4, 2023, 04:01 PM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based tools for digital transformation, today announced financial and operating results for the first quarter 2023 and issued guida

May 3, 2023 EX-4.1

Tax Benefit Preservation Plan, dated as of May 2, 2023, by and between Upland Software, Inc. and Broadridge Corporate Issuer Solutions, LLC, as rights agent.

EXECUTION VERSION TAX BENEFIT PRESERVATION PLAN by and between Upland Software, Inc.

May 3, 2023 8-A12B

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) OR 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 UPLAND SOFTWARE, INC. (Exact name of registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) OR 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 UPLAND SOFTWARE, INC.

May 3, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 May 2, 2023 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC. (E

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 May 2, 2023 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

May 3, 2023 EX-3.1

Certificate of Designations of Series B Junior Participating Preferred Stock of Upland Software, Inc., filed with the Secretary of State of the State of Delaware on May 2, 2023.

CERTIFICATE OF DESIGNATIONS of SERIES B JUNIOR PARTICIPATING PREFERRED STOCK of UPLAND SOFTWARE, INC.

May 3, 2023 EX-99.1

Upland Software, Inc. Adopts Tax Benefit Preservation Plan for Net Operating Losses

EXHIBIT 99.1 Upland Software, Inc. Adopts Tax Benefit Preservation Plan for Net Operating Losses May 3, 2023, 09:00 AM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)-Upland Software, Inc. (“Upland”) (NASDAQ: UPLD) announced today that its Board of Directors (the “Board”) has adopted a tax benefit preservation plan (the “Plan”) designed to preserve the availability of its net operating loss ca

April 28, 2023 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ý Defin

April 17, 2023 PRE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: ý Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) o Defin

March 2, 2023 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Table Form S-8 (Form Type) Upland Software, Inc.

March 2, 2023 S-8

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM S-8 REGISTRATION STATEMENT Under The Securities Act of 1933 UPLAND SOFTWARE, INC. (Exact name of registrant as specified in its charter) Delaware 27-2992077 (State or other ju

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM S-8 REGISTRATION STATEMENT Under The Securities Act of 1933 UPLAND SOFTWARE, INC.

March 1, 2023 EX-2.11

List of subsidiaries of Upland Software, Inc.

Exhibit 21.1 List of Subsidiaries of Upland Software, Inc. as of December 31, 2022 Upland Software Inc. Upland Software UK Limited Upland Software Australia Pty Ltd Upland Software India Private Limited Upland Software Ireland Limited Return Fax 2000 Ltd. Rapide Communications Ltd. Rant & Rave Limited Wire-E Limited 66099 Limited Adestra Limited Adestra Pty Limited Altify, Ltd. BlueVenn Group Limi

March 1, 2023 EX-4.2

Description of Capital Stock

Exhibit 4.2 DESCRIPTION OF CAPITAL STOCK This section describes the general terms and provisions of the shares of our common stock, par value of $0.0001 per share, and preferred stock, par value of $0.0001 per share. This description is only a summary. Our restated certificate of incorporation and our bylaws have been filed as exhibits to our periodic reports filed with the SEC, which are incorpor

March 1, 2023 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 ☐ TRANSITION REPORT PURSUANT TO SECTI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission File Number 001-36720 Upland Software, Inc. (Exact name of registrant as specified

February 23, 2023 EX-10.1

Amendment No. 1 to Credit Agreement, dated as of February 21, 2023, by and between Upland Software, Inc. and Credit Suisse AG, Cayman Islands Branch, as administrative agent and collateral agent

Execution Version AMENDMENT NO. 1 TO CREDIT AGREEMENT This AMENDMENT NO. 1 TO CREDIT AGREEMENT, dated as of February 21, 2023 (this “Amendment”), is entered into by and among, UPLAND SOFTWARE, INC., a Delaware corporation (the “Borrower”) and CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, as administrative agent and collateral agent for each member of the Lender Group and the Bank Product Providers (in

February 23, 2023 EX-99.1

Upland Software Reports Fourth Quarter 2022 Financial Results Company Beats Q4 Revenue Guidance and Announces Comprehensive Growth Plan

EXHIBIT 99.1 Upland Software Reports Fourth Quarter 2022 Financial Results Company Beats Q4 Revenue Guidance and Announces Comprehensive Growth Plan February 23, 2023, 04:01 PM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based tools for digital transformation, today announced financial and operating results for the fourth quarter 202

February 23, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 February 21, 2023 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 February 21, 2023 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

February 9, 2023 SC 13G

UPLD / Upland Software Inc / VANGUARD GROUP INC - SCHEDULE 13G Passive Investment

SC 13G 1 tv02140-uplandsoftwareinc.htm SCHEDULE 13G SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 Name of issuer: Upland Software Inc. Title of Class of Securities: Common Stock CUSIP Number: 91544A109 Date of Event Which Requires Filing of this Statement: December 30, 2022 Check the appropriate box to designate the rule pursuant t

February 8, 2023 SC 13G/A

UPLD / Upland Software Inc / Marathon Asset Mgmt Ltd - UPLAND SOFTWARE 13G Passive Investment

Schedule 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No.1)* Upland Software, Inc. (Name of Issuer) Ordinary shares (Title of Class of Securities) 91544A109 (CUSIP Number) James Bennett, Chief Risk and Compliance Officer, Marathon Asset Management Limited, Orion House, 5 Upper St. Martin’s Lane, London

November 3, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2022 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36720

November 3, 2022 EX-99.1

Upland Software Reports Third Quarter 2022 Financial Results

EXHIBIT 99.1 Upland Software Reports Third Quarter 2022 Financial Results November 3, 2022, 04:01 PM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based tools for digital transformation, today announced financial and operating results for the third quarter 2022 and issued guidance for its fourth quarter and full year of 2022. Third Qua

November 3, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 November 3, 2022 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

October 28, 2022 CORRESP

Upland Software, Inc. 401 Congress Ave, Suite 1850 Austin, Texas 78701 October 28, 2022

Upland Software, Inc. 401 Congress Ave, Suite 1850 Austin, Texas 78701 October 28, 2022 VIA EDGAR Kyle Wiley Division of Corporation Finance United States Securities and Exchange Commission 100 F Street, NE Washington, D.C. 20549 Re: Upland Software, Inc. Registration Statement on Form S-3 (File No. 333-267973) Dear Mr. Wiley, Pursuant to Rule 461 under the Securities Act of 1933, as amended, Upla

October 21, 2022 EX-FILING FEES

Calculation of Filing Fee tables

Exhibit 107 Calculation of Filing Fee Tables FORM S-3 (Form Type) Upland Software, Inc.

October 21, 2022 SC 13D/A

UPLD / Upland Software Inc / MCDONALD JOHN T - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Rule 13d-101) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO § 240.13d-1(a) AND AMENDMENTS THERETO FILED PURSUANT TO § 240.13d-2(a) (Amendment No. 1)* Upland Software, Inc. (Name of Issuer) Common Stock, Par Value $0.0001 Per Share (Title of Class of Securities) 91544A109 (CUSIP Number) John T. McDona

October 21, 2022 S-3

As filed with the Securities and Exchange Commission on October 21, 2022

As filed with the Securities and Exchange Commission on October 21, 2022 Registration No.

August 25, 2022 SC 13D

UPLD / Upland Software Inc / ULYSSES AGGREGATOR, LP - SCHEDULE 13D Activist Investment

SC 13D 1 ea164855-sc13dulyssesupland.htm SCHEDULE 13D UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. )* UPLAND SOFTWARE, INC. (Name of Issuer) Common Stock, par value $0.0001 per share (Title of Class of Securities) 91544A109 (CUSIP Number) David Chung Ulysses Aggregator, LP c/o HGGC, LLC 1950 University

August 25, 2022 EX-99.1

Joint Filing Agreement, dated as of August 25, 2022, by and among the Reporting Persons (filed herewith).

Exhibit 99.1 JOINT FILING AGREEMENT The persons below hereby agree that the Schedule 13D to which this agreement is attached as an exhibit, as well as all future amendments to such Schedule 13D, shall be filed jointly on behalf of each of them. This agreement is intended to satisfy the requirements of Rule 13d-1(k)(1)(iii) under the Securities Exchange Act of 1934. Dated: August 25, 2022 ULYSSES A

August 23, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Entry into a Material Definitive Agreement, Material Modification to Rights of Security Holders, Unregistered Sales of Equity Securities, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 August 23, 2022 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

August 23, 2022 EX-3.1

Certificate of Designation of Preferences, Rights and Limitations of Series A Convertible Preferred Stock

Exhibit 3.1 Final Form CERTIFICATE OF DESIGNATION OF SERIES A CONVERTIBLE PREFERRED STOCK OF UPLAND SOFTWARE, INC. (Pursuant to Section 151 of the General Corporation Law of the State of Delaware) Upland Software, Inc., a corporation organized and existing under the General Corporation Law of the State of Delaware (hereinafter, the ?Corporation?), hereby certifies that the following resolution was

August 23, 2022 EX-10.1

Registration Rights Agreement, by and between Upland Software, Inc. and Ulysses Aggregator, LP, dated as of August 23, 2022

Exhibit 10.1 Execution Version REGISTRATION RIGHTS AGREEMENT BY AND AMONG UPLAND SOFTWARE, INC., AND ULYSSES AGGREGATOR, L.P. Dated as of August 23, 2022 TABLE OF CONTENTS Page Article I Resale Shelf Registration 1 Section 1.1 Resale Shelf Registration Statement 1 Section 1.2 Effectiveness Period 2 Section 1.3 Subsequent Shelf Registration 2 Section 1.4 Supplements and Amendments 3 Section 1.5 Sub

August 9, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2022 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36720 UPLA

August 3, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 August 3, 2022 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

August 3, 2022 EX-99.1

Upland Software Reports Second Quarter 2022 Financial Results

EXHIBIT 99.1 Upland Software Reports Second Quarter 2022 Financial Results August 3, 2022, 04:01 PM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based tools for digital transformation, today announced financial and operating results for the second quarter 2022 and issued guidance for its third quarter and full year of 2022. Second Qua

July 14, 2022 8-K

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 July 14, 2022 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

July 14, 2022 EX-99.1

Upland Software Announces $115 Million Strategic Equity Investment From HGGC Investment By Leading Private Equity Firm Provides Incremental Capital for Future M&A Opportunities and Brings Value-Added Support for Long Term Value Creation

EXHIBIT 99.1 Upland Software Announces $115 Million Strategic Equity Investment From HGGC Investment By Leading Private Equity Firm Provides Incremental Capital for Future M&A Opportunities and Brings Value-Added Support for Long Term Value Creation July 14, 2022, 08:01 AM Central Standard Time AUSTIN, Texas ? (BUSINESS WIRE) ? Upland Software, Inc. (NASDAQ: UPLD) announced today a $115 million st

July 14, 2022 EX-10.1

Securities Purchase Agreement, by and between Upland Software, Inc. and Ulysses Aggregator, LP, dated as of July 14, 2022

EXHIBIT 10.1 Execution Version SECURITIES PURCHASE AGREEMENT BY AND BETWEEN UPLAND SOFTWARE, INC., AND ULYSSES AGGREGATOR, LP Dated as of July 14, 2022 TABLE OF CONTENTS Page ARTICLE I PURCHASE AND SALE OF PURCHASED SHARES 1 Section 1.1 Purchase and Sale 1 Section 1.2 Closing 1 ARTICLE II REPRESENTATIONS AND WARRANTIES OF THE COMPANY 2 Section 2.1 Organization and Power 2 Section 2.2 Authorization

June 13, 2022 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 June 8, 2022 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

May 4, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2022 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36720 UPL

May 4, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 May 4, 2022 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

May 4, 2022 EX-99.1

Upland Software Reports First Quarter 2022 Financial Results

EXHIBIT 99.1 Upland Software Reports First Quarter 2022 Financial Results May 4, 2022, 04:01 PM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based tools for digital transformation, today announced financial and operating results for the first quarter 2022 and issued guidance for its second quarter and full year of 2022. First Quarter

April 29, 2022 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Defin

March 2, 2022 S-8

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM S-8 REGISTRATION STATEMENT Under The Securities Act of 1933 UPLAND SOFTWARE, INC. (Exact name of registrant as specified in its charter) Delaware 27-2992077 (State or other ju

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM S-8 REGISTRATION STATEMENT Under The Securities Act of 1933 UPLAND SOFTWARE, INC.

March 2, 2022 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Table Form S-8 (Form Type) Upland Software, Inc.

February 24, 2022 EX-21.1

List of subsidiaries of Upland Software, Inc.

Exhibit 21.1 List of Subsidiaries of Upland Software, Inc. as of December 31, 2021 Upland Software Inc. Upland Software UK Limited Upland Software Australia Pty Ltd Upland Software India Private Limited Interfax Communications Limited Return Fax 2000 Ltd. Rapide Communications Ltd. Rant & Rave Limited Wire-E Limited 66099 Limited Adestra Limited Adestra Pty Limited Altify Ireland Limited Altify, L

February 24, 2022 EX-10.33

Employment Agreement between the Registrant and

Exhibit 10.33 UPLAND SOFTWARE, INC. EXECUTIVE EMPLOYMENT AGREEMENT This Executive Employment Agreement (the ?Agreement?) is entered into as of January 12, 2022 (the ?Effective Date?) by and between Upland Software, Inc., a Delaware corporation (the ?Company?), and Kin Gill (?Executive?). RECITALS WHEREAS, the Company and Executive desire to memorialize the terms of employment of Executive as of th

February 24, 2022 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 ☐ TRANSITION REPORT PURSUANT TO SECTI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission File Number 001-36720 Upland Software, Inc. (Exact name of registrant as specified

February 24, 2022 EX-4.2

Description of Capital Stock

Exhibit 4.2 DESCRIPTION OF CAPITAL STOCK This section describes the general terms and provisions of the shares of our common stock, par value of $0.0001 per share, and preferred stock, par value of $0.0001 per share. This description is only a summary. Our restated certificate of incorporation and our bylaws have been filed as exhibits to our periodic reports filed with the SEC, which are incorpor

February 24, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 February 24, 2022 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

February 24, 2022 EX-99.1

Upland Software Reports Fourth Quarter and Full Year 2021 Financial Results and Announces Acquisition of BA Insight

EXHIBIT 99.1 Upland Software Reports Fourth Quarter and Full Year 2021 Financial Results and Announces Acquisition of BA Insight February 24, 2022, 04:01 PM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based tools for digital transformation, today announced financial and operating results for the fourth quarter and full year of 2021 a

February 8, 2022 SC 13G/A

UPLD / Upland Software Inc / CDAM (UK) Ltd Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No.

January 28, 2022 SC 13G

UPLD / Upland Software Inc / Marathon Asset Mgmt Ltd - UPLAND SOFTWARE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Upland Software, Inc. (Name of Issuer) Common stock, par value $0.0001 per share (Title of Class of Securities) 91544A109 (CUSIP Number) James Bennett, Chief Risk & Compliance Officer, Marathon Asset Management Limited, Orion House, 5 Upper St. Martin?s L

January 10, 2022 EX-99.1

Upland Software Acquires Objectif Lune

Exhibit 99.1 Upland Software Acquires Objectif Lune January 10, 2022 9:01 AM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD) announced that it has acquired Objectif Lune Inc., an enterprise software leader in document composition and business communication automation. With the addition of Objectif Lune, Upland expands its global document workflow product l

January 10, 2022 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 January 10, 2022 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

November 3, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 November 3, 2021 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

November 3, 2021 EX-99.1

Upland Software Reports Third Quarter 2021 Financial Results

EXHIBIT 99.1 Upland Software Reports Third Quarter 2021 Financial Results November 3, 2021, 04:01 PM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based tools for digital transformation, today announced financial and operating results for the third quarter of 2021 and revised guidance for its fourth quarter and full year of 2021. Third

November 3, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36720

August 4, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 August 4, 2021 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

August 4, 2021 EX-99.1

Upland Software Reports Second Quarter 2021 Financial Results

EXHIBIT 99.1 Upland Software Reports Second Quarter 2021 Financial Results August 4, 2021, 04:01 PM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based tools for digital transformation, today announced financial and operating results for the second quarter of 2021 and issued guidance for its third quarter and full year of 2021. Second

August 4, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36720 UPLA

July 9, 2021 SC 13G/A

UPLD / Upland Software Inc / ESW Capital, LLC - SC 13G/A Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No.

June 24, 2021 EX-99.1

Upland Software Acquires Panviva and Raises Guidance

Exhibit 99.1 Upland Software Acquires Panviva and Raises Guidance June 24, 2021 8:01 AM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD) announced that it has acquired Panviva Pty Ltd, a cloud-based enterprise knowledge management solution. With the addition of Panviva, Upland has expanded its presence within the knowledge management market, giving customer

June 24, 2021 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 June 24, 2021 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

June 10, 2021 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 June 9, 2021 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

May 26, 2021 SC 13G

UPLD / Upland Software Inc / ESW Capital, LLC - SC 13G Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 Schedule 13G to amend the Schedule 13D filed by ESW Capital, LLC and related parties on May 24, 2021 UPLAND SOFTWARE, INC (Name of Issuer) Common Stock, par value $0.

May 26, 2021 EX-99.1

Exhibit 99.1

Exhibit 99.1 JOINT FILING AGREEMENT In accordance with Rule 13d-1(k)(1) promulgated under the Securities Exchange Act of 1934, the undersigned agree to the joint filing of a Statement on Schedule 13G (including any and all amendments thereto) with respect to the Common Stock, $0.0001 par value per share, of Upland Software, Inc. and further agree to the filing of this agreement as an exhibit there

May 24, 2021 SC 13D/A

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. 11)* UPLAND SOFTWARE, INC.

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. 11)* 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 AVENU

May 24, 2021 EX-99.A

Exhibit A

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.

May 5, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 May 5, 2021 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

May 5, 2021 EX-99.1

Upland Software Reports First Quarter 2021 Financial Results

EXHIBIT 99.1 Upland Software Reports First Quarter 2021 Financial Results May 5, 2021, 04:01 PM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based tools for digital transformation, today announced financial and operating results for the first quarter of 2021 and issued guidance for its second quarter and full year of 2021. First Quart

May 5, 2021 EX-10.1

Advisory Agreement between Upland Software, Inc. and Tim Mattox effective March 31, 2021.

Exhibit 10.1 UPLAND SOFTWARE, INC. ADVISORY AGREEMENT This Advisory Agreement (the ?Agreement?) is made and entered into effective as of March 31, 2021, by and between Upland Software, Inc., a Delaware corporation (the ?Company?), and Tim Mattox (the ?Advisor?). WHEREAS, from July 14, 2014 through March 2, 2021 the Advisor was employed as co-President & COO of the Company and he will be employed b

May 5, 2021 10-Q

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36720 UPL

April 30, 2021 DEF 14A

- DEF 14A -2021

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Defin

March 2, 2021 EX-99.1

Upland Software Acquires BlueVenn

Exhibit 99.1 Upland Software Acquires BlueVenn March 2, 2021, 9:04 AM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD) announced that it has acquired BlueVenn, a leading cloud-based customer data platform (CDP). With BlueVenn, Upland customers can now securely unify their consumer data, unlocking the insights needed to create omnichannel digital engagement

March 2, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 March 2, 2021 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

March 2, 2021 EX-99.1

Upland Software Acquires BlueVenn

Exhibit 99.1 Upland Software Acquires BlueVenn March 2, 2021, 9:04 AM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD) announced that it has acquired BlueVenn, a leading cloud-based customer data platform (CDP). With BlueVenn, Upland customers can now securely unify their consumer data, unlocking the insights needed to create omnichannel digital engagement

March 2, 2021 8-K/A

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 March 2, 2021 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

February 26, 2021 S-8

- S-8

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM S-8 REGISTRATION STATEMENT Under The Securities Act of 1933 UPLAND SOFTWARE, INC.

February 25, 2021 EX-10.31

Amendment #2 to Employment Agreement between the Registrant and John T. McDonald, dated March 28, 2017

Exhibit 10.31 Amendment # 2 to UPLAND SOFTWARE, INC. EXECUTIVE EMPLOYMENT AGREEMENT This Amendment #2 to the Executive Employment Agreement by and between Upland Software, Inc., a Delaware corporation (the ?Company?) and John T. McDonald (?Executive?) dated March 28, 2017 and amended March 13, 2019 (?Original Agreement?), is entered into as of November 12, 2020. RECITALS WHEREAS, the Company and E

February 25, 2021 EX-10.32

Amendment #1 to Employment Agreement between the Registrant and Rodney C. Favaron, dated March 1, 2020

Exhibit 10.32 Amendment # 1 to UPLAND SOFTWARE, INC. EXECUTIVE EMPLOYMENT AGREEMENT This Amendment #1 to the Executive Employment Agreement by and between Upland Software, Inc., a Delaware corporation (the ?Company?) and Rodney C. Favaron (?Executive?) dated March 1, 2020 (?Original Agreement?), is entered into as of November 12, 2020. RECITALS WHEREAS, the Company and Executive desire to amend Pa

February 25, 2021 EX-4.2

Description of Capital Stock

Exhibit 4.2 DESCRIPTION OF CAPITAL STOCK This section describes the general terms and provisions of the shares of our common stock, par value of $0.0001 per share, and preferred stock, par value of $0.0001 per share. This description is only a summary. Our restated certificate of incorporation and our bylaws have been filed as exhibits to our periodic reports filed with the SEC, which are incorpor

February 25, 2021 10-K

Annual Report - 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2020 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission File Number 001-36720 Upland Software, Inc. (Exact name of registrant as specified

February 25, 2021 EX-10.28

Employment Agreement between Registrant and Rodney C. Favaron, dated March 1, 2020

Exhibit 10.28 UPLAND SOFTWARE, Inc. EXECUTIVE EMPLOYMENT AGREEMENT This Executive Employment Agreement (the ?Agreement?) is entered into as of March 1, 2020 (the ?Effective Date?) by and between Upland Software, Inc., a Delaware corporation (the ?Company?), and Rodney C. Favaron (?Executive?). RECITALS WHEREAS, the Company and Executive desire to memorialize the terms of employment of Executive as

February 25, 2021 EX-10.30

Amendment #2 to Employment Agreement between the Registrant and Timothy Mattox, dated March 28, 2017

Exhibit 10.30 Amendment # 2 to UPLAND SOFTWARE, INC. EXECUTIVE EMPLOYMENT AGREEMENT This Amendment #2 to the Executive Employment Agreement by and between Upland Software, Inc., a Delaware corporation (the ?Company?) and Timothy Mattox (?Executive?) dated March 28, 2017 and amended March 13, 2019 (?Original Agreement?), is entered into as of November 12, 2020. RECITALS WHEREAS, the Company and Exe

February 25, 2021 EX-10.29

Amendment #2 to Employment Agreement between the Registrant and Michael D. Hill, dated March 28, 2017

EX-10.29 4 exhibit1029-hillamendment2.htm EX-10.29 Exhibit 10.29 Amendment # 2 to UPLAND SOFTWARE, INC. EXECUTIVE EMPLOYMENT AGREEMENT This Amendment #2 to the Executive Employment Agreement by and between Upland Software, Inc., a Delaware corporation (the “Company”) and Michael D. Hill (“Executive”) dated March 28, 2017 and amended March 13, 2019 (“Original Agreement”), is entered into as of Nove

February 25, 2021 EX-21.1

List of subsidiaries of Upland Software, Inc.

Exhibit 21.1 List of Subsidiaries of Upland Software, Inc. as of December 31, 2020 Upland Software, Inc./Logiciels Upland Inc. Upland Software I, Inc. Upland Software UK Limited Omtool, Ltd. InterFax Communications Limited Return Fax 2000 Ltd Data Guard Limited Rapide Communication Ltd. Rant & Rave Limited Wire-E Limited 66099 Limited Adestra Limited Adestra Pty Limited Altify Ireland Limited Alti

February 24, 2021 EX-99.1

Upland Software Reports Fourth Quarter and Full Year 2020 Financial Results

EXHIBIT 99.1 Upland Software Reports Fourth Quarter and Full Year 2020 Financial Results February 24, 2021, 04:01 PM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based tools for digital transformation, today announced financial and operating results for the fourth quarter and full year of 2020 and issued guidance for its first quarter

February 24, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 February 24, 2021 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

February 11, 2021 SC 13G

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Upland Software, Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No.

January 20, 2021 EX-99.1

Upland Software Acquires Second Street

Exhibit 99.1 Upland Software Acquires Second Street January 20, 2021, 09:04 AM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)— Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based tools for digital transformation, has acquired Second Street Media, Inc., a leading audience engagement cloud software platform. Adding Second Street to Upland’s product portfolio will provide Upland’s cust

January 20, 2021 8-K

Financial Statements and Exhibits, Other Events - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 January 20, 2021 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

November 6, 2020 10-Q

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2020 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36720

November 5, 2020 EX-99.1

Upland Software Reports Third Quarter 2020 Financial Results

EXHIBIT 99.1 Upland Software Reports Third Quarter 2020 Financial Results November 5, 2020, 04:01 PM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based tools for digital transformation, today announced financial and operating results for the third quarter of 2020 and raised guidance for its fourth quarter and full year of 2020. Third

November 5, 2020 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 November 5, 2020 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

August 28, 2020 8-K

Other Events - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 August 26, 2020 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

August 14, 2020 EX-1.01

, 2020, by and among Upland Software, Inc. and Credit Suisse Securities (USA) LLC, as representatives of the several underwriters named therein.

3,500,000 Shares Upland Software, Inc. Common Stock UNDERWRITING AGREEMENT August 11, 2020 Credit Suisse Securities (USA) LLC As Representative of the Several Underwriters c/o Credit Suisse Securities (USA) LLC, Eleven Madison Avenue, New York, N.Y. 10010-3629 Ladies and Gentlemen: 1. Introductory. Upland Software, Inc., a Delaware corporation (the “Company”) agrees with the several Underwriters n

August 14, 2020 EX-5.01

Pillsbury Winthrop Shaw Pittman LLP.

Exhibit 5.01 PILLSBURY WINTHROP SHAW PITTMAN LLP 401 Congress Avenue, Suite 1700, Austin, TX 78701 August 14, 2020 Upland Software, Inc. 401 Congress Avenue, Suite 1850 Austin, Texas 78701 Ladies and Gentlemen: We have acted as counsel for Upland Software, Inc., a Delaware corporation (the “Company”), in connection with the issuance and sale of 4,025,000 shares (the “Shares”) of common stock, $0.0

August 14, 2020 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 August 11, 2020 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

August 12, 2020 424B5

CALCULATION OF REGISTRATION FEE

TABLE OF CONTENTS  Filed Pursuant to Rule 424(b)(5)  Registration No. 333-243728 CALCULATION OF REGISTRATION FEE Title of each class of securities to be registered Amount to be registered(1) Maximum Offering Price Per Share Maximum Aggregate Offering Price Amount of Registration Fee(2)(3) Common stock, $0.0001 par value per share 4,025,000 $ 34.00 $ 136,850,000 $ 17,763.13 (1) Includes shares of C

August 10, 2020 EX-99.1

Upland Software Announces Proposed Public Offering of Common Stock

Upland Software Announces Proposed Public Offering of Common Stock AUSTIN, Texas, August 10, 2020 - Upland Software, Inc.

August 10, 2020 S-3ASR

-

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on August 10, 2020 Registration No.

August 10, 2020 424B3

SUBJECT TO COMPLETION, DATED AUGUST 10, 2020

TABLE OF CONTENTS This preliminary prospectus supplement relates to an effective registration statement under the Securities Act of 1933, but the information in this preliminary prospectus supplement is not complete and may be changed.

August 10, 2020 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 August 10, 2020 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

August 7, 2020 10-Q

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2020 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36720 UPLA

August 6, 2020 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 August 6, 2020 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

August 6, 2020 EX-99.1

Upland Software Reports Second Quarter 2020 Financial Results

EXHIBIT 99.1 Upland Software Reports Second Quarter 2020 Financial Results August 6, 2020, 04:01 PM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based tools for digital transformation, today announced financial and operating results for the second quarter of 2020 and raised guidance for its third quarter and full year of 2020. Second

June 11, 2020 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 June 10, 2020 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

May 8, 2020 10-Q

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2020 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36720 UPL

May 7, 2020 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 May 7, 2020 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

May 7, 2020 EX-99.1

Upland Software Reports First Quarter 2020 Financial Results

EXHIBIT 99.1 Upland Software Reports First Quarter 2020 Financial Results May 7, 2020, 04:01 PM Eastern Standard Time AUSTIN, Texas-(BUSINESS WIRE)- Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based enterprise work management software, today announced financial and operating results for the first quarter of 2020 and provided guidance for its second quarter and full year of 2020. First

April 27, 2020 DEF 14A

Definitive Proxy Statement on Schedule 14A filed with the SEC on April 27, 2020

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ý Defin

March 6, 2020 S-8

UPLD / Upland Software, Inc. S-8 - - S-8 2020 EVERGREEN

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM S-8 REGISTRATION STATEMENT Under The Securities Act of 1933 UPLAND SOFTWARE, INC.

March 2, 2020 EX-21.1

List of subsidiaries of Upland Software, Inc.

EXHIBIT 21.1 List of Subsidiaries of Upland Software, Inc. as of December 31, 2019 Upland Software, Inc./Logiciels Upland Inc. Upland Software I, Inc. Upland Software IV, LLC Upland Software VI, LLC Upland Software VII, LLC Upland IX, LLC Ultriva, LLC Upland Software UK Limited Omtool, Ltd. RightAnswers, Inc. Waterfall International, Inc. Qvidian Corporation InterFax Communications Limited Return

March 2, 2020 10-K

Annual Report - 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2019 OR ¨ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission File Number 001-36720 Upland Software, Inc. (Exact name of registrant as specified

March 2, 2020 EX-4.2

Description of Capital Stock

EXHIBIT 4.2 DESCRIPTION OF CAPITAL STOCK This section describes the general terms and provisions of the shares of our common stock, par value of $0.0001 per share, and preferred stock, par value of $0.0001 per share. This description is only a summary. Our restated certificate of incorporation and our bylaws have been filed as exhibits to our periodic reports filed with the SEC, which are incorpor

February 28, 2020 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 February 24, 2020 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

February 26, 2020 EX-99.1

Upland Software Reports Fourth Quarter and Full Year 2019 Financial Results

EXHIBIT 99.1 Upland Software Reports Fourth Quarter and Full Year 2019 Financial Results AUSTIN, Texas, February 26, 2020 /Businesswire/ - Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based enterprise work management software, today announced financial and operating results for the fourth quarter and full year of 2019 and reaffirmed guidance for its first quarter and full year of 2020.

February 26, 2020 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 February 26, 2020 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

February 14, 2020 SC 13G/A

UPLD / Upland Software, Inc. / Portolan Capital Management, LLC - SCHEDULE 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULES 13d –1(b), (c), AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d–2. (Amendment No. 1 )* Upland Software, Inc. (Name of Issuer) Common (Title of Class of Securities) 91544A109 (CUSIP Number) December 31, 2019 (Date of Event Which Requires Fil

February 7, 2020 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 February 7, 2020 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

February 7, 2020 EX-99.1

Upland Software Acquires Localytics, Raises Guidance Accretive acquisition adds $20 million in annualized revenues and leading mobile app personalization technology to Upland’s Customer Experience Management Cloud

Exhibit 99.1 Upland Software Acquires Localytics, Raises Guidance Accretive acquisition adds $20 million in annualized revenues and leading mobile app personalization technology to Upland’s Customer Experience Management Cloud AUSTIN – February 7, 2020 /PRNewswire/ – Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based enterprise work management software, has acquired Localytics, a leadin

February 4, 2020 EX-99.1

Upland Software Names Rod Favaron President and Chief Commercial Officer Industry veteran with proven track record joins to scale go-to-market across sales, marketing, and customer success

Upland Software Names Rod Favaron President and Chief Commercial Officer Industry veteran with proven track record joins to scale go-to-market across sales, marketing, and customer success AUSTIN – February 4, 2020 /Business Wire/ – Upland Software, Inc.

February 4, 2020 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 February 3, 2020 Date of Report (Date of earliest event reported) UPLAND SOFTWARE, INC.

February 4, 2020 EX-3.1

Amended and Restated By-laws of Upland Software, Inc., effective February 3, 2020

AMENDED AND RESTATED BYLAWS OF UPLAND SOFTWARE, INC. (as amended and restated on February 3, 2020) TABLE OF CONTENTS Page ARTICLE I - CORPORATE OFFICES 1 1.1 REGISTERED OFFICE 1 1.2 OTHER OFFICES 1 ARTICLE II - MEETINGS OF STOCKHOLDERS 1 2.1 PLACE OF MEETINGS 1 2.2 ANNUAL MEETING 1 2.3 SPECIAL MEETING 1 2.4 ADVANCE NOTICE PROCEDURES 2 2.5 NOTICE OF STOCKHOLDERS’ MEETINGS 5 2.6 QUORUM 6 2.7 ADJOURN

November 26, 2019 EX-10.01

First Incremental Assumption Agreement by and among, inter alios, Upland Software, Inc. and Credit Suisse AG, Cayman Islands Branch, as Agent and 2019 Incremental Lender, dated as of November 26, 2019

FIRST INCREMENTAL ASSUMPTION AGREEMENT This FIRST Incremental Assumption Agreement, dated as of November 26, 2019 (this “Agreement”), is made by and among Credit Suisse AG, Cayman Islands Branch (the “2019 Incremental Lender”), Upland Software, Inc.

November 26, 2019 8-K

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported) November 26, 2019 UPLAND SOFTWARE, INC.

November 26, 2019 EX-99.1

Upland Software Announces New $190 Million Incremental Term Loan to Fund Future Accretive Acquisitions

Upland Software Announces New $190 Million Incremental Term Loan to Fund Future Accretive Acquisitions AUSTIN, Texas – Nov.

November 13, 2019 8-K

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported) November 13, 2019 UPLAND SOFTWARE, INC.

November 12, 2019 10-Q

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2019 OR ¨ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36720

November 7, 2019 8-K

Results of Operations and Financial Condition, 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported) November 7, 2019 UPLAND SOFTWARE, INC.

November 7, 2019 EX-99..1

Upland Software Reports Third Quarter 2019 Financial Results

EXHIBIT 99.1 Upland Software Reports Third Quarter 2019 Financial Results AUSTIN, Texas, November 7, 2019 /Businesswire/ - Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based enterprise work management software, today announced financial and operating results for the third quarter of 2019 and provided guidance for its fourth quarter and full year of 2019. Third Quarter 2019 Financial Hig

October 21, 2019 SC 13G

UPLD / Upland Software, Inc. / Portolan Capital Management, LLC - SC 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULES 13d –1(b), (c), AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d–2. (Amendment No. )* Upland Software, Inc. (Name of Issuer) Common (Title of Class of Securities) 91544A109 (CUSIP Number) October 11, 2019 (Date of Event Which Requires Filing

October 7, 2019 8-K

Financial Statements and Exhibits, Completion of Acquisition or Disposition of Assets, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported) October 4, 2019 UPLAND SOFTWARE, INC.

October 7, 2019 EX-10.4

Share Purchase Agreement by and among PowerSteering UK, Aine Denn, and Roy Enright as sellers' representative, dated as of October 4, 2019.

EXECUTION VERSION DATE 4 October 2019 (1) THE PERSONS WHOSE NAMES AND ADDRESSES ARE SET OUT IN SCHEDULE 1 (2) POWERSTEERING SOFTWARE LIMITED (3) ROY ENRIGHT (AS SELLERS’ REPRESENTATIVE) SHORT FORM SHARE PURCHASE AGREEMENT relating to the acquisition of certain of the issued share capital of ALTIFY IRELAND LIMITED Pillsbury Winthrop Shaw Pittman LLP Tower 42, Level 21 25 Old Broad Street London EC2N 1HQ TABLE OF CONTENTS Page 1.

October 7, 2019 EX-10.5

Short Form Share Purchase Agreement by and among PowerSteering UK, the minority sellers of Altify named therein, and Roy Enright, as sellers' representative, dated as of October 4, 2019.

EXECUTION VERSION DATE 4 October 2019 (1) ÁINE DENN (2) POWERSTEERING SOFTWARE LIMITED (3) ROY ENRIGHT (AS SELLERS’ REPRESENTATIVE) SHORT FORM SHARE PURCHASE AGREEMENT relating to the acquisition of certain of the issued share capital of ALTIFY IRELAND LIMITED Pillsbury Winthrop Shaw Pittman LLP Tower 42, Level 21 25 Old Broad Street London EC2N 1HQ TABLE OF CONTENTS Page 1.

October 7, 2019 EX-99.1

Upland Software Acquires Altify, Raises Guidance Accretive acquisition of customer revenue optimization solution adds $24 million in annualized revenues and core platform for Upland’s Sales Optimization solution suite

Upland Software Acquires Altify, Raises Guidance Accretive acquisition of customer revenue optimization solution adds $24 million in annualized revenues and core platform for Upland’s Sales Optimization solution suite AUSTIN - October 7, 2019 /Business Wire/ - Upland Software, Inc.

October 7, 2019 EX-10.2

Share Purchase Agreement by and among PowerSteering UK, the option sellers of Altify named therein, and Roy Enright, as sellers' representative, dated as of October 4, 2019.

EXECUTION VERSION DATE October 4, 2019 (1) ALTIFY LIMITED ON BEHALF OF THE PERSONS WHOSE NAMES AND ADDRESSES ARE SET OUT IN SCHEDULE 1 (2) POWERSTEERING SOFTWARE LIMITED (3) ALTIFY IRELAND LIMITED (4) ROY ENRIGHT (AS SELLERS' REPRESENTATIVE) OPTION SHARE PURCHASE AGREEMENT relating to the acquisition of certain of the issued share capital of ALTIFY IRELAND LIMITED Pillsbury Winthrop Shaw Pittman LLP Tower 42, Level 21 25 Old Broad Street London EC2N 1HQ TABLE OF CONTENTS Page 1.

October 7, 2019 EX-10.1

Share Purchase Agreement by and among PowerSteering UK, the sellers of shares of Altify named therein, and Roy Enright, as sellers' representative, dated as of October 4, 2019.

EXECUTION VERSION DATE 4 October 2019 (1) THE PERSONS WHOSE NAMES AND ADDRESSES ARE SET OUT IN PART 1 OF SCHEDULE 1 (2) POWERSTEERING SOFTWARE LIMITED (3) ROY ENRIGHT (AS SELLERS’ REPRESENTATIVE) SHARE PURCHASE AGREEMENT relating to the acquisition of certain of the issued share capital of ALTIFY IRELAND LIMITED Pillsbury Winthrop Shaw Pittman LLP Tower 42, Level 21 25 Old Broad Street London EC2N 1HQ EXECUTION VERSION TABLE OF CONTENTS Page 1.

October 7, 2019 EX-10.3

Share Purchase Agreement by and among PowerSteering UK, the beneficial owners of Altify Limited, a company listed under the laws of England and Wales and a wholly-owned subsidiary of Altify, and Roy Enright, as sellers' representative, dated as of October 4, 2019.

EXECUTION VERSION DATE 4 October 2019 (1) ALTIFY LIMITED ON BEHALF OF THE PERSONS WHOSE NAMES AND ADDRESSES ARE SET OUT IN SCHEDULE 1 (2) POWERSTEERING SOFTWARE LIMITED (3) ALTIFY IRELAND LIMITED (4) ROY ENRIGHT (AS SELLERS' REPRESENTATIVE) ALTIFY UK SHARE PURCHASE AGREEMENT relating to the acquisition of certain of the issued share capital of ALTIFY IRELAND LIMITED Pillsbury Winthrop Shaw Pittman LLP Tower 42, Level 21 25 Old Broad Street London EC2N 1HQ TABLE OF CONTENTS Page 1.

October 1, 2019 EX-99.1

Upland Software Announces Acquisition, Raises Guidance Acquisition of InGenius establishes first Contact Center Productivity solution suite with native CRM agent communications, knowledge management, and customer sentiment analysis

Upland Software Announces Acquisition, Raises Guidance Acquisition of InGenius establishes first Contact Center Productivity solution suite with native CRM agent communications, knowledge management, and customer sentiment analysis AUSTIN - October 1, 2019 /Business Wire/ - Upland Software, Inc.

October 1, 2019 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported) October 1, 2019 UPLAND SOFTWARE, INC.

August 22, 2019 EX-99.1

Upland Software Announces Acquisition, Raises Guidance Acquisition of Cimpl creates first IT Financial Management Cloud with enterprise-class Telecom Expense Management capabilities

Upland Software Announces Acquisition, Raises Guidance Acquisition of Cimpl creates first IT Financial Management Cloud with enterprise-class Telecom Expense Management capabilities AUSTIN - August 22, 2019 /Business Wire/ - Upland Software, Inc.

August 22, 2019 8-K/A

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported) August 22, 2019 UPLAND SOFTWARE, INC.

August 22, 2019 EX-99.1

Upland Software Announces Acquisition, Raises Guidance Acquisition of Cimpl creates first IT Financial Management Cloud with enterprise-class Telecom Expense Management capabilities

Upland Software Announces Acquisition, Raises Guidance Acquisition of Cimpl creates first IT Financial Management Cloud with enterprise-class Telecom Expense Management capabilities AUSTIN - August 22, 2019 /Business Wire/ - Upland Software, Inc.

August 22, 2019 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported) August 22, 2019 UPLAND SOFTWARE, INC.

August 9, 2019 10-Q

Quarterly Report - FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2019 OR ¨ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36720 UPLA

August 7, 2019 EX-99.1

Upland Software Completes $410 Million Financing Transaction Upgraded credit facilities provide additional capital for growth

Upland Software Completes $410 Million Financing Transaction Upgraded credit facilities provide additional capital for growth AUSTIN, Texas - Aug.

August 7, 2019 8-K

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Termination of a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported) August 5, 2019 UPLAND SOFTWARE, INC.

August 7, 2019 EX-10.1

Credit Agreement by and among, inter alios, Upland Software, Inc., Credit Suisse AG, Cayman Islands Branch and the lenders party thereto Credit Agreement by and among, inter alios, Upland Software, Inc., Credit Suisse AG, Cayman Islands Branch and the lenders party thereto dated as of August 6, 2019 as of August 6, 2019

CREDIT AGREEMENT by and among CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, as Agent, WELLS FARGO BANK, NATIONAL ASSOCIATION, as Syndication Agent, CAPITAL ONE, NATIONAL ASSOCIATION, HSBC BANK USA, NATIONAL ASSOCIATION AND REGIONS BANK as Co-Documentation Agents, THE LENDERS THAT ARE PARTIES HERETO FROM TIME TO TIME, as the Lenders, UPLAND SOFTWARE, INC.

August 7, 2019 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported) August 7, 2019 UPLAND SOFTWARE, INC.

August 7, 2019 EX-99.1

Upland Software Reports Second Quarter 2019 Financial Results

EXHIBIT 99.1 Upland Software Reports Second Quarter 2019 Financial Results AUSTIN, Texas, August 7, 2019 /Businesswire/ - Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based enterprise work management software, today announced financial and operating results for the second quarter of 2019 and provided guidance for its third quarter and full year of 2019. Second Quarter 2019 Financial Hig

July 1, 2019 8-K

Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported) June 27, 2019 UPLAND SOFTWARE, INC.

June 12, 2019 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported) June 12, 2019 UPLAND SOFTWARE, INC.

June 11, 2019 8-K

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported) June 11, 2019 UPLAND SOFTWARE, INC.

May 28, 2019 EX-10.1

Agreement and Plan of Merger by and among Upland Software, Inc., Hammerhead Acquisition Corporation, Daily Inches, Inc., and Epic Start Consulting, LLC, solely in its capacity as Stockholder Representative dated as of May 23, 2019.

Exhibit 10.1 [*] Indicates that certain information in this exhibit has been excluded because it is both (i) not material and (ii) would be competitively harmful if publicly disclosed. AGREEMENT AND PLAN OF MERGER BY AND AMONG UPLAND SOFTWARE, INC., HAMMERHEAD ACQUISITION CORPORATION, DAILY INCHES, INC. AND EPIC START CONSULTING, LLC, AS STOCKHOLDER REPRESENTATIVE dated as of May 23, 2019 AGREEMEN

May 28, 2019 EX-99.1

Upland Software Acquires Kapost, Raises Guidance Accretive acquisition adds $15 million in annualized revenues, strong customer base, and robust content operations solution for sales and marketing

Upland Software Acquires Kapost, Raises Guidance Accretive acquisition adds $15 million in annualized revenues, strong customer base, and robust content operations solution for sales and marketing AUSTIN – May 28, 2019 /Business Wire/ – Upland Software, Inc.

May 28, 2019 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported) May 24, 2019 UPLAND SOFTWARE, INC.

May 14, 2019 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported) May 13, 2019 UPLAND SOFTWARE, INC.

May 10, 2019 424B5

3,300,000 Shares UPLAND SOFTWARE, INC. Common Stock

Use these links to rapidly review the document TABLE OF CONTENTS TABLE OF CONTENTS Table of Contents Filed Pursuant to Rule 424(b)(5) Registration No.

May 9, 2019 EX-1.01

Underwriting Agreement, dated May 8, 2019, by and among Upland Software, Inc. and Credit Suisse Securities (USA) LLC and Jefferies LLC, as representatives of the several underwriters named therein (incorporated by reference to Exhibit 1.01 of the Company's Current Report on Form 8-K, file number 001-36720, filed with the Securities and Exchange Commission on May 9, 2019).

Execution Version 3,300,000 Upland Software, Inc. Common Stock UNDERWRITING AGREEMENT May 8, 2019 CREDIT SUISSE SECURITIES (USA) LLC JEFFERIES LLC As Representatives of the Several Underwriters c/o Credit Suisse Securities (USA) LLC, Eleven Madison Avenue, New York, N.Y. 10010-3629 c/o Jefferies LLC 520 Madison Avenue New York, N.Y. 10022 Dear Sirs: 1. Introductory. Upland Software, Inc., a Delawa

May 9, 2019 EX-99.1

Upland Software Announces Pricing of Public Offering of Common Stock

Upland Software Announces Pricing of Public Offering of Common Stock AUSTIN, Texas, May 8, 2019 - Upland Software, Inc.

May 9, 2019 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported) May 8, 2019 UPLAND SOFTWARE, INC.

May 6, 2019 424B3

SUBJECT TO COMPLETION, DATED MAY 6, 2019

Use these links to rapidly review the document TABLE OF CONTENTS TABLE OF CONTENTS Table of Contents Filed Pursuant to Rule 424(b)(3) Registration No.

May 6, 2019 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported) May 6, 2019 UPLAND SOFTWARE, INC.

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