Form 8-K

8-K — Upland Software, Inc.

Accession: 0001505155-26-000068

Filed: 2026-08-14

Period: 2026-08-14

CIK: 0001505155

SIC: 7372 (SERVICES-PREPACKAGED SOFTWARE)

Item: Results of Operations and Financial Condition

Item: Financial Statements and Exhibits

Documents

8-K — upld-20260814.htm (Primary)

EX-99.1 (q226991earningsrelease.htm)

XML — IDEA: XBRL DOCUMENT (R1.htm)

8-K

8-K (Primary)

Filename: upld-20260814.htm · Sequence: 1

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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 14, 2026

Date of Report (Date of earliest event reported)

UPLAND SOFTWARE, INC.

(Exact name of registrant as specified in its charter)

Delaware 001-36720 27-2992077

(State or other jurisdiction of incorporation) (Commission File Number) (IRS Employer

Identification No.)

900 S. Capital of Texas Highway, Las Cimas IV, Suite 300

Austin, Texas 78746

(Address of principal executive offices, including zip code)

(512) 960-1010

(Registrant’s telephone number, including area code)

Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions (see General Instruction A.2. below):

☐ Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)

☐ Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)

☐ Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))

☐ Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))

Securities registered pursuant to Section 12(b) of the Act:

Title of each class Trading Symbol Name of each exchange on which registered

Common Stock, par value $0.0001 per share UPLD The Nasdaq Global Market

Preferred Stock Purchase Rights - The Nasdaq Global Market

Indicate by check mark whether the registrant is an emerging growth company as defined in Rule 405 of the Securities Act of 1933 (§230.405 of this chapter) or Rule 12b-2 of the Securities Exchange Act of 1934 (§240.12b-2 of this chapter).

Emerging growth company ☐

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ☐

Item 2.02 Results of Operations and Financial Condition.

On August 14, 2026, the Company issued a press release announcing its financial results for the quarter ended June 30, 2026. The full text of the press release is attached hereto as Exhibit 99.1 and is incorporated herein by reference.

Item 9.01 Financial Statements and Exhibits.

(d) Exhibits.

Exhibit No.

Description

99.1

Press Release of Upland Software, Inc. dated August 14, 2026

104 The cover page from this Current Report on Form 8-K, formatted as Inline XBRL

SIGNATURE

Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned thereunto duly authorized.

UPLAND SOFTWARE, INC.

By: /s/ David Tamez

David Tamez

Interim Chief Financial Officer

Date: August 14, 2026

EX-99.1

Filename: q226991earningsrelease.htm · Sequence: 2

Document

EXHIBIT 99.1

Upland Software Reports Second Quarter 2026 Financial Results

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 2026 and issued guidance for its third quarter and full year of 2026.

Second Quarter 2026 Financial Highlights

•Total revenue was $49.1 million, a decrease of 8% from $53.4 million in the second quarter of 2025, primarily due to divestitures completed in 2025.

•Subscription and support revenue was $46.2 million, a decrease of 9% from $50.5 million in the second quarter of 2025, primarily due to divestitures completed in 2025.

•GAAP net loss was $35.3 million compared to a GAAP net loss of $13.0 million in the second quarter of 2025, primarily due to a non-cash goodwill impairment recorded in June 2026. Non-GAAP net income was $6.6 million, an increase of 18% from $5.6 million in the second quarter of 2025.

•Adjusted EBITDA was $12.8 million, or 26% of total revenue, compared to $13.6 million, or 25% of total revenue, in the second quarter of 2025.

•GAAP operating cash flow was $5.4 million, compared to GAAP operating cash flow of $3.3 million in the second quarter of 2025. Free cash flow was $5.3 million, compared to free cash flow of $2.7 million in the second quarter of 2025.

•Cash on hand as of the end of the second quarter of 2026 was $31.0 million.

"We are still in the early innings of building the company I described in my shareholder letter issued on July 28, 2026 - one that concentrates capital where we believe we can actually win and turns our AI advantage into both revenue growth and operating margin expansion," said Sean Nathaniel, Upland's President and Chief Executive Officer. "Q2 gave us real proof points along that path. We exceeded the midpoints on both revenue and Adjusted EBITDA, added 81 new customers, and earned notable industry recognitions. While there is more work ahead, like sharpening our operating groups around the areas with the clearest AI land-grab opportunity and deleveraging the balance sheet, the groundwork being laid today is what the next chapter of Upland will be built on."

Second Quarter Business Highlights

•We welcomed 81 new customers to Upland in the second quarter, including 7 new major customers. We also expanded relationships with 200 existing customers, 19 of which were major expansions.

•Upland was recognized in Forrester's "The Knowledge Management Solutions Landscape, Q2 2026," published June 22, 2026. We believe our inclusion in this report showcases the strength of our knowledge management offering, Upland RightAnswers, in a market being reshaped by the shift from human-only to agent-automated knowledge management. The report notes that of the extended use cases Forrester identified, Upland reported a focus on agentic curation automation, knowledge as AI infrastructure, and secure knowledge sharing, reflecting its investment in helping knowledge serve both human users and AI agents alike.

•We earned 43 badges in G2's Summer 2026 market reports, reflecting the real AI impact our solutions deliver for customers. Upland Panviva and Upland RightAnswers, our leading AI-powered knowledge management solutions, earned numerous badges, with Panviva earning 12 across contact center knowledge base, customer self-service, and knowledge management categories. Upland BA Insight, our AI enablement solution, continued to secure recognition from customers, and Upland InterFAX, our AI-enabled cloud fax service, also received several badges, proving ongoing value to customers on their AI journeys.

Business Outlook

For the quarter ending September 30, 2026, Upland expects reported total revenue to be between $45.7 and $48.7 million, including subscription and support revenue between $43.7 and $46.2 million, for a decline in total revenue of 7% at the midpoint from the quarter ended September 30, 2025. This year-over-year revenue decline is primarily due to divestitures completed in 2025. Third quarter 2026 Adjusted EBITDA is expected to be between $11.9 and $13.4 million, which at the midpoint is a decline of 21% from the quarter ended September 30, 2025. Third quarter 2026 Adjusted EBITDA margin is expected to be 27% at the midpoint as compared to the 32% Adjusted EBITDA margin for the quarter ended September 30, 2025.

For the full year ending December 31, 2026, Upland expects reported total revenue to be between $190.1 and $196.1 million, including subscription and support revenue between $180.0 and $185.0 million, for a decline in total revenue of 11% at the midpoint from the year ended December 31, 2025. This year-over-year revenue decline is primarily due to divestitures completed in 2025. Full year 2026 Adjusted EBITDA is expected to be between $49.8 and $52.8 million, which at the midpoint is a decline of 12% from the year ended December 31, 2025. Full year 2026 Adjusted EBITDA margin is expected to be 27% at the midpoint as compared to the 27% Adjusted EBITDA margin for the year ended December 31, 2025.

About Upland Software

Upland Software (Nasdaq: UPLD) provides an intelligence layer that unifies and contextualizes enterprise knowledge, content, and data, turning isolated information into actionable outcomes for every human and agent. More than 1,100 enterprise customers rely on Upland's deep domain expertise to drive measurable, value-add outcomes, unlocking the full potential of AI as their organizations evolve. For more information, visit www.uplandsoftware.com.

Non-GAAP Financial Measures

To supplement our consolidated financial statements, which are prepared and presented in accordance with GAAP, we use the following non-GAAP financial measures: Adjusted EBITDA, non-GAAP net income (loss), non-GAAP net income (loss) per share, and Free Cash Flow.

We use these non-GAAP financial measures for financial and operational decision-making and as a means to evaluate period-to-period comparisons. Our management believes that these non-GAAP financial measures provide meaningful supplemental information regarding our performance and liquidity by excluding certain expenses and expenditures that may not be indicative of our recurring core business operating results, such as our revenues excluding the impact for foreign currency fluctuations or our operating performance excluding not only non-cash charges, but also discrete cash charges that are infrequent in nature. We believe that both management and investors benefit from referring to these non-GAAP financial measures in assessing our performance and when planning, forecasting, and analyzing future periods. These non-GAAP financial measures also facilitate management's internal comparisons to our historical performance and liquidity as well as comparisons to our competitors' operating results. We believe these non-GAAP financial measures are useful to investors both because they allow for greater transparency with respect to key metrics used by management in its financial and operational decision-making and they are used by our institutional investors and the analyst community to help them analyze the health of our business. For a reconciliation of these non-GAAP financial measures to the most directly comparable GAAP financial measures, see the tables provided below in this release.

We are unable to reconcile any forward-looking non-GAAP financial measures to their directly comparable GAAP financial measures because the information which is needed to complete a reconciliation is unavailable at this time without unreasonable effort. Additionally, we are unable to quantify the impact of foreign currency exchange fluctuations on components of our income statement beyond revenues because the information which is needed to do so is unavailable at this time without unreasonable effort.

Upland defines Adjusted EBITDA as net income (loss), calculated in accordance with GAAP, plus depreciation and amortization expense, interest expense, net, other expense (income), net, provision (benefit) for income taxes, stock-based compensation expense, acquisition and divestiture-related expenses, non-recurring litigation costs, purchase accounting adjustments for deferred revenue, loss on divestitures and impairment charges.

Upland defines non-GAAP net income (loss) as net income (loss), calculated in accordance with GAAP, plus amortization of purchased intangible assets, amortization of debt discount, loss on debt extinguishment, stock-based compensation expenses, acquisition and divestiture-related expenses, non-recurring litigation expenses, purchase accounting adjustments for deferred revenue, non-recurring effects of provision for income tax, loss on divestitures, impairment charges and the related tax effect of the adjustments above.

Upland defines Free Cash Flow as GAAP operating cash flow less purchases of property and equipment.

Upland defines major accounts as accounts with greater than or equal to $25,000 in annual recurring revenue.

Upland defines major expansions as existing customers who expanded the amount of annual recurring revenue under their contract by at least $25,000.

In connection with periodic reviews of our business, we discontinued the availability of certain non-strategic product offerings and a limited number of non-strategic customer contracts (collectively referred to as “Sunset Assets”).

Forward-looking Statements

This release contains "forward-looking statements" within the meaning of Section 27A of the Securities Act, and Section 21E of the Securities Exchange Act of 1934, as amended. Forward-looking statements generally relate to future events or our future financial or operating performance, including our guidance related to future performance, and are subject to substantial risks, uncertainties and assumptions. We may not actually achieve the plans, intentions, or expectations disclosed in our forward-looking statements. Our forward-looking statements do not reflect the potential impact of any future acquisitions, mergers, dispositions, joint ventures, or investments we may make. Accordingly, you should not place undue reliance on these forward-looking statements. Forward-looking statements include any statement that does not directly relate to any historical or current fact and often include words such as “anticipate,” “believe,” “may,” “will,” “continue,” “seek,” “estimate,” “intend,” “hope,” “predict,” “could,” “should,” “would,” “project,” “plan,” “expect” or the negative or plural of these words or similar expressions, although not all forward-looking statements contain these words.

Actual results may differ materially from those indicated by such forward-looking statements as a result of various important factors, including, but are not limited to: our financial performance and our ability to achieve or sustain profitability or predict future results; our plans regarding future acquisitions and divestitures and our ability to consummate and operationalize acquisitions or divestitures; our ability to expand our go-to-market operations, including our marketing and sales organization, and successfully increase sales of our products; our ability to obtain financing in the future on acceptable terms or at all; our expectations with respect to revenue, cost of revenue, and operating expenses in future periods; our expectations with regard to revenue from perpetual licenses and professional services; our ability to adapt to macroeconomic factors impacting the global economy, including global conflicts and uncertainty, changes in trade policy, foreign currency exchange risk, inflation and supply chain constraints; our ability to attract and retain customers; our ability to successfully enter new markets and manage our international expansion; our ability to comply with privacy laws and regulations; our ability to incorporate and deliver artificial intelligence (“AI”) functionality into our products and services, including our ability to unlock critical knowledge, automate content workflows and drive measurable ROI; our ability to deliver high-quality customer service; our plans regarding, and our ability to effectively manage, our growth, including with respect to our growth investments; maintaining our senior management team and key personnel; the performance of our resellers; our ability to adapt to changing market conditions and competition; our ability to adapt to technological change and continue to innovate; global economic and financial market conditions and uncertainties; the growth of demand for cloud-based, digital transformation applications; our ability to integrate our applications with other software applications; maintaining and expanding our relationships with third parties; costs associated with defending intellectual property infringement and other claims; our ability to maintain, protect and enhance our brand and intellectual property; our expectations with regard to trends, such as seasonality, which affect our business; impairments to goodwill and other intangible assets; our beliefs regarding how our applications benefit customers and what our competitive strengths are; the operation, reliability and security of our third-party data centers; our expectations as to the timing of the discontinuation of any Sunset Assets, as well as the composition of Sunset Assets; our expectations as to the payment of dividends; our 2025 Share Repurchase Plan, including expectations regarding the timing and manner of repurchases made under the Share Repurchase Plan; our current level of indebtedness, including our exposure to variable interest rate risk; the potential elimination or limitation of tax incentives or tax losses and/or reductions of U.S. federal net operating losses; the risk that we did not consider another contingency included in this list; and factors that could affect our business and financial results identified in Upland's filings with the Securities and Exchange Commission (the "SEC"), including Upland's most recent 10-K filed with the SEC. Additional information

will also be set forth in Upland's future quarterly reports on Form 10-Q, annual reports on Form 10-K and other filings that Upland makes with the SEC.

The forward-looking statements herein represent Upland's views as of the date of this press release, and these views could change. However, while Upland may elect to update these forward-looking statements at some point in the future, Upland specifically disclaims any obligation to do so, except as required by law. These forward-looking statements should not be relied upon as representing the views of Upland as of any date subsequent to the date of this press release.

Forrester does not endorse any company, product, brand, or service included in its research publications and does not advise any person to select the products or services of any company or brand based on the ratings included in such publications. Information is based on the best available resources. Opinions reflect judgment at the time and are subject to change. This report is part of a broader collection of Forrester resources, including interactive models, frameworks, tools, data, and access to analyst guidance. For more information, read about Forrester’s objectivity at https://www.forrester.com/about-us/objectivity/.

###

Investor Relations Contact:

David Tamez

investor-relations@uplandsoftware.com

512-960-1031

Media Contact:

Lloyd Berry

media@uplandsoftware.com

512-960-1010

Upland Software, Inc.

Condensed Consolidated Statements of Operations

(in thousands, except per share data)

Three Months Ended June 30, Six Months Ended June 30,

2026 2025 2026 2025

(unaudited) (unaudited) (unaudited) (unaudited)

Revenue:

Subscription and support $ 46,152 $ 50,467 $ 92,243 $ 110,649

Perpetual license 1,738 1,199 3,033 2,807

Total product revenue 47,890 51,666 95,276 113,456

Professional services 1,251 1,717 2,555 3,582

Total revenue 49,141 53,383 97,831 117,038

Cost of revenue:

Subscription and support 10,871 12,412 21,983 29,362

Professional services and other 799 1,023 1,621 2,121

Total cost of revenue 11,670 13,435 23,604 31,483

Gross profit 37,471 39,948 74,227 85,555

Operating expenses:

Sales and marketing 9,509 10,771 18,981 24,527

Research and development 7,766 9,781 15,810 21,323

General and administrative 9,065 10,219 17,603 21,840

Depreciation and amortization 5,579 6,864 11,210 14,859

Divestiture-related expenses — 6,879 22 8,624

Impairment of goodwill and other intangibles 35,246 2,469 35,246 2,469

Total operating expenses 67,165 46,983 98,872 93,642

Loss from operations (29,694) (7,035) (24,645) (8,087)

Other income (expense):

Interest expense, net (4,526) (4,136) (8,985) (6,579)

Loss on divestitures of businesses — (434) — (23,891)

Other expense, net (257) (1,595) (1,091) (1,836)

Total other expense, net (4,783) (6,165) (10,076) (32,306)

Loss before benefit from (provision for) income taxes (34,477) (13,200) (34,721) (40,393)

Benefit from (provision for) income taxes (841) 171 (1,827) 1,516

Net loss $ (35,318) $ (13,029) $ (36,548) $ (38,877)

Preferred stock dividends (1,521) (1,454) (3,024) (2,892)

Net loss attributable to common stockholders $ (36,839) $ (14,483) $ (39,572) $ (41,769)

Net loss per common share:

Net loss per common share, basic and diluted $ (12.53) $ (5.08) $ (13.52) $ (14.72)

Weighted average common shares outstanding:

Weighted-average common shares outstanding, basic and diluted 2,939,547 2,851,884 2,927,789 2,837,071

Upland Software, Inc.

Condensed Consolidated Balance Sheets

(in thousands)

June 30, December 31,

2026 2025

(unaudited)

ASSETS

Current assets:

Cash and cash equivalents $ 31,044 $ 29,398

Restricted cash 626 626

Accounts receivable, net of allowance 19,850 25,603

Deferred commissions, current 5,339 5,660

Unbilled receivables 3,723 3,981

Income tax receivable, current 3,871 1,832

Prepaid expenses and other current assets 5,657 8,154

Total current assets 70,110 75,254

Tax credits receivable 969 863

Property and equipment, net 1,550 1,815

Operating lease right-of-use asset 1,400 1,713

Intangible assets, net 48,814 62,317

Goodwill 222,693 259,631

Deferred commissions, noncurrent 7,573 7,865

Interest rate derivatives 120 15

Other assets 3,337 3,704

Total assets $ 356,566 $ 413,177

LIABILITIES, CONVERTIBLE PREFERRED STOCK AND STOCKHOLDERS' DEFICIT

Current liabilities:

Accounts payable $ 2,457 $ 2,140

Accrued compensation 4,064 4,358

Accrued expenses and other current liabilities 2,829 3,938

Deferred revenue 66,102 74,768

Operating lease liabilities, current 646 817

Current maturities of notes payable 4,120 7,739

Total current liabilities 80,218 93,760

Notes payable, less current maturities 219,723 224,667

Deferred revenue, noncurrent 5,510 4,841

Operating lease liabilities, noncurrent 1,769 1,971

Noncurrent deferred tax liability, net 6,378 6,723

Other long-term liabilities 619 505

Total liabilities 314,217 332,467

Series A Convertible Preferred stock 132,102 129,078

Stockholders’ deficit:

Common stock

— —

Additional paid-in capital 605,917 607,278

Accumulated other comprehensive loss (18,614) (15,138)

Accumulated deficit (677,056) (640,508)

Total stockholders’ deficit (89,753) (48,368)

Total liabilities, convertible preferred stock and stockholders’ deficit $ 356,566 $ 413,177

Upland Software, Inc.

Condensed Consolidated Statements of Cash Flows

(in thousands)

Three Months Ended June 30, Six Months Ended June 30,

2026 2025 2026 2025

(unaudited) (unaudited) (unaudited) (unaudited)

Operating activities

Net loss $ (35,318) $ (13,029) $ (36,548) $ (38,877)

Adjustments to reconcile net income (loss) to net cash provided by operating activities:

Depreciation and amortization 6,430 8,155 13,054 17,816

Deferred income taxes (180) (454) (176) (3,532)

Amortization of deferred costs 1,686 1,918 3,373 4,653

Foreign currency re-measurement loss 237 895 1,119 1,355

Non-cash interest, net and other income, net (797) 565 (1,696) (621)

Non-cash stock-based compensation expense 830 3,074 1,791 5,749

Non-cash loss on impairment of goodwill and other intangibles 35,246 2,469 35,246 2,469

Non-cash loss on divestitures of businesses — 434 — 23,891

Non-cash loss on retirement of fixed assets — 50 2 52

Changes in operating assets and liabilities:

Accounts receivable 3,738 3,287 5,603 11,258

Prepaid expenses and other current assets 710 1,792 565 (727)

Other assets (1,485) (1,222) (3,014) (3,189)

Accounts payable 173 2,204 337 (4,994)

Accrued expenses and other liabilities 701 (1,422) (1,204) 1,072

Deferred revenue (6,601) (5,427) (7,479) (4,781)

Net cash provided by operating activities 5,370 3,289 10,973 11,594

Investing activities

Purchase of property and equipment (87) (634) (168) (1,058)

Collections on note receivable 184 — 361 —

Proceeds from the divestitures of businesses, net of cash transferred — 4,850 — 9,063

Net cash provided by investing activities 97 4,216 193 8,005

Financing activities

Payments on notes payable (4,103) (1,349) (8,925) (35,575)

Payments of debt issuance costs (30) (4) (243) (7)

Taxes paid related to net share settlement of equity awards (53) (186) (127) (680)

Net cash used in financing activities (4,186) (1,539) (9,295) (36,262)

Effect of exchange rate fluctuations on cash, cash equivalents and restricted cash (18) 1,340 (225) 1,248

Change in cash, cash equivalents and restricted cash 1,263 7,306 1,646 (15,415)

Cash, cash equivalents and restricted cash, beginning of period 30,407 34,331 30,024 57,052

Cash, cash equivalents and restricted cash, end of period $ 31,670 $ 41,637 $ 31,670 $ 41,637

Supplemental disclosures of cash flow information:

Cash paid for interest, net of interest rate derivatives $ 5,782 $ 3,886 $ 11,596 $ 8,048

Cash paid for taxes, net of refunds $ 2,184 $ 3,172 $ 5,053 $ 5,148

Non-cash investing and financing activities:

Note receivable from divestiture of businesses, net of discount $ — $ 4,881 $ — $ 4,881

Upland Software, Inc.

Reconciliation of Adjusted EBITDA

(in thousands)

Three Months Ended June 30, Six Months Ended June 30,

2026 2025 2026 2025

(unaudited) (unaudited) (unaudited) (unaudited)

Reconciliation of Net Loss to Adjusted EBITDA:

Net loss $ (35,318) $ (13,029) $ (36,548) $ (38,877)

Add:

Depreciation and amortization expense 6,430 8,155 13,054 17,816

Interest expense (income), net 4,526 4,136 8,985 6,579

Other expense (income), net 257 1,595 1,091 1,836

Provision for (benefit from) income taxes 841 (171) 1,827 (1,516)

Stock-based compensation expense 830 3,074 1,791 5,749

Divestiture-related expenses — 6,879 22 8,624

Non-recurring litigation costs — 12 1 30

Purchase accounting deferred revenue discount 8 31 21 66

Loss on divestitures of businesses — 434 — 23,891

Impairment of goodwill and other intangibles 35,246 2,469 35,246 2,469

Adjusted EBITDA $ 12,820 $ 13,585 $ 25,490 $ 26,667

Upland Software, Inc.

Reconciliation of Non-GAAP Net Loss and Non-GAAP EPS

(in thousands, except share and per share data)

Three Months Ended June 30, Six Months Ended June 30,

2026 2025 2026 2025

(unaudited) (unaudited) (unaudited) (unaudited)

Reconciliation of Net Loss to Non-GAAP Net Income:

Net loss $ (35,318) $ (13,029) $ (36,548) $ (38,877)

Add:

Stock-based compensation expense 830 3,074 1,791 5,749

Amortization of purchased intangibles 6,227 7,892 12,638 17,292

Amortization of debt discount 329 545 656 1,085

Divestiture-related expenses — 6,879 22 8,624

Non-recurring litigation expense — 12 1 30

Purchase accounting deferred revenue discount 8 31 21 66

Loss on divestitures of businesses — 434 — 23,891

Impairment of goodwill and other intangibles 35,246 2,469 35,246 2,469

Tax effect of adjustments above (726) (2,727) (1,291) (6,540)

Non-GAAP net income $ 6,596 $ 5,580 $ 12,536 $ 13,789

Weighted average common shares outstanding, basic 2,939,547 2,851,884 2,927,789 2,837,071

Weighted average common shares outstanding, diluted 3,714,874 3,609,637 3,701,043 3,600,321

Non-GAAP earnings per share, basic $ 2.24 $ 1.96 $ 4.28 $ 4.86

Non-GAAP earnings per share, diluted $ 1.78 $ 1.55 $ 3.39 $ 3.83

Upland Software, Inc.

Reconciliation of Operating Cash Flow to Free Cash Flow

(in thousands)

Three Months Ended June 30, Six Months Ended June 30,

2026 2025 2026 2025

(unaudited) (unaudited) (unaudited) (unaudited)

Reconciliation of operating cash flow to Free Cash Flow:

Net cash provided by operating activities $ 5,370 $ 3,289 $ 10,973 $ 11,594

Less: Purchase of property and equipment (87) (634) (168) (1,058)

Free Cash Flow $ 5,283 $ 2,655 $ 10,805 $ 10,536

Upland Software, Inc.

Supplemental Financial Information

(in thousands)

Three Months Ended June 30, Six Months Ended June 30,

2026 2025 2026 2025

(unaudited) (unaudited) (unaudited) (unaudited)

Stock-based compensation:

Cost of revenue $ 72 $ 143 $ 158 $ 264

Research and development 57 318 140 608

Sales and marketing 13 52 43 304

General and administrative 688 2,561 1,450 4,573

Total $ 830 $ 3,074 $ 1,791 $ 5,749

Three Months Ended June 30, Six Months Ended June 30,

2026 2025 2026 2025

(unaudited) (unaudited) (unaudited) (unaudited)

Depreciation:

Operating expense $ 203 $ 263 $ 416 $ 524

Total $ 203 $ 263 $ 416 $ 524

Amortization:

Cost of revenue $ 851 $ 1,291 $ 1,844 $ 2,957

Operating expense 5,376 6,601 10,794 14,335

Total $ 6,227 $ 7,892 $ 12,638 $ 17,292

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Aug. 14, 2026

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Document Period End Date

Aug. 14, 2026

Entity Registrant Name

UPLAND SOFTWARE, INC.

Entity Incorporation, State or Country Code

Entity File Number

001-36720

Entity Tax Identification Number

27-2992077

Entity Address, Address Line One

900 S. Capital of Texas Highway, Las Cimas IV, Suite 300

Entity Address, City or Town

Austin

Entity Address, State or Province

Entity Address, Postal Zip Code

78746

City Area Code

512

Local Phone Number

960-1010

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Document Information [Line Items]

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Trading Symbol

UPLD

Security Exchange Name

NASDAQ

Preferred Stock Purchase Rights

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Security Exchange Name

NASDAQ

No Trading Symbol Flag

true

- Definition

Boolean flag that is true when the XBRL content amends previously-filed or accepted submission.

+ References

No definition available.

+ Details

Name:

dei_AmendmentFlag

Namespace Prefix:

dei_

Data Type:

xbrli:booleanItemType

Balance Type:

Period Type:

duration

- Definition

Area code of city

+ References

No definition available.

+ Details

Name:

dei_CityAreaCode

Namespace Prefix:

dei_

Data Type:

xbrli:normalizedStringItemType

Balance Type:

Period Type:

duration

- Definition

Line items represent financial concepts included in a table. These concepts are used to disclose reportable information associated with domain members defined in one or many axes to the table.

+ References

No definition available.

+ Details

Name:

dei_DocumentInformationLineItems

Namespace Prefix:

dei_

Data Type:

xbrli:stringItemType

Balance Type:

Period Type:

duration

- Definition

For the EDGAR submission types of Form 8-K: the date of the report, the date of the earliest event reported; for the EDGAR submission types of Form N-1A: the filing date; for all other submission types: the end of the reporting or transition period. The format of the date is YYYY-MM-DD.

+ References

No definition available.

+ Details

Name:

dei_DocumentPeriodEndDate

Namespace Prefix:

dei_

Data Type:

xbrli:dateItemType

Balance Type:

Period Type:

duration

- Definition

The type of document being provided (such as 10-K, 10-Q, 485BPOS, etc). The document type is limited to the same value as the supporting SEC submission type, or the word 'Other'.

+ References

No definition available.

+ Details

Name:

dei_DocumentType

Namespace Prefix:

dei_

Data Type:

dei:submissionTypeItemType

Balance Type:

Period Type:

duration

- Definition

Address Line 1 such as Attn, Building Name, Street Name

+ References

No definition available.

+ Details

Name:

dei_EntityAddressAddressLine1

Namespace Prefix:

dei_

Data Type:

xbrli:normalizedStringItemType

Balance Type:

Period Type:

duration

- Definition

Name of the City or Town

+ References

No definition available.

+ Details

Name:

dei_EntityAddressCityOrTown

Namespace Prefix:

dei_

Data Type:

xbrli:normalizedStringItemType

Balance Type:

Period Type:

duration

- Definition

Code for the postal or zip code

+ References

No definition available.

+ Details

Name:

dei_EntityAddressPostalZipCode

Namespace Prefix:

dei_

Data Type:

xbrli:normalizedStringItemType

Balance Type:

Period Type:

duration

- Definition

Name of the state or province.

+ References

No definition available.

+ Details

Name:

dei_EntityAddressStateOrProvince

Namespace Prefix:

dei_

Data Type:

dei:stateOrProvinceItemType

Balance Type:

Period Type:

duration

- Definition

A unique 10-digit SEC-issued value to identify entities that have filed disclosures with the SEC. It is commonly abbreviated as CIK.

+ References

Reference 1: http://www.xbrl.org/2003/role/presentationRef

-Publisher SEC

-Name Exchange Act

-Number 240

-Section 12

-Subsection b-2

+ Details

Name:

dei_EntityCentralIndexKey

Namespace Prefix:

dei_

Data Type:

dei:centralIndexKeyItemType

Balance Type:

Period Type:

duration

- Definition

Indicate if registrant meets the emerging growth company criteria.

+ References

Reference 1: http://www.xbrl.org/2003/role/presentationRef

-Publisher SEC

-Name Exchange Act

-Number 240

-Section 12

-Subsection b-2

+ Details

Name:

dei_EntityEmergingGrowthCompany

Namespace Prefix:

dei_

Data Type:

xbrli:booleanItemType

Balance Type:

Period Type:

duration

- Definition

Commission file number. The field allows up to 17 characters. The prefix may contain 1-3 digits, the sequence number may contain 1-8 digits, the optional suffix may contain 1-4 characters, and the fields are separated with a hyphen.

+ References

No definition available.

+ Details

Name:

dei_EntityFileNumber

Namespace Prefix:

dei_

Data Type:

dei:fileNumberItemType

Balance Type:

Period Type:

duration

- Definition

Two-character EDGAR code representing the state or country of incorporation.

+ References

No definition available.

+ Details

Name:

dei_EntityIncorporationStateCountryCode

Namespace Prefix:

dei_

Data Type:

dei:edgarStateCountryItemType

Balance Type:

Period Type:

duration

- Definition

The exact name of the entity filing the report as specified in its charter, which is required by forms filed with the SEC.

+ References

Reference 1: http://www.xbrl.org/2003/role/presentationRef

-Publisher SEC

-Name Exchange Act

-Number 240

-Section 12

-Subsection b-2

+ Details

Name:

dei_EntityRegistrantName

Namespace Prefix:

dei_

Data Type:

xbrli:normalizedStringItemType

Balance Type:

Period Type:

duration

- Definition

The Tax Identification Number (TIN), also known as an Employer Identification Number (EIN), is a unique 9-digit value assigned by the IRS.

+ References

Reference 1: http://www.xbrl.org/2003/role/presentationRef

-Publisher SEC

-Name Exchange Act

-Number 240

-Section 12

-Subsection b-2

+ Details

Name:

dei_EntityTaxIdentificationNumber

Namespace Prefix:

dei_

Data Type:

dei:employerIdItemType

Balance Type:

Period Type:

duration

- Definition

Local phone number for entity.

+ References

No definition available.

+ Details

Name:

dei_LocalPhoneNumber

Namespace Prefix:

dei_

Data Type:

xbrli:normalizedStringItemType

Balance Type:

Period Type:

duration

- Definition

Boolean flag that is true only for a security having no trading symbol.

+ References

No definition available.

+ Details

Name:

dei_NoTradingSymbolFlag

Namespace Prefix:

dei_

Data Type:

dei:trueItemType

Balance Type:

Period Type:

duration

- Definition

Boolean flag that is true when the Form 8-K filing is intended to satisfy the filing obligation of the registrant as pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act.

+ References

Reference 1: http://www.xbrl.org/2003/role/presentationRef

-Publisher SEC

-Name Exchange Act

-Number 240

-Section 13e

-Subsection 4c

+ Details

Name:

dei_PreCommencementIssuerTenderOffer

Namespace Prefix:

dei_

Data Type:

xbrli:booleanItemType

Balance Type:

Period Type:

duration

- Definition

Boolean flag that is true when the Form 8-K filing is intended to satisfy the filing obligation of the registrant as pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act.

+ References

Reference 1: http://www.xbrl.org/2003/role/presentationRef

-Publisher SEC

-Name Exchange Act

-Number 240

-Section 14d

-Subsection 2b

+ Details

Name:

dei_PreCommencementTenderOffer

Namespace Prefix:

dei_

Data Type:

xbrli:booleanItemType

Balance Type:

Period Type:

duration

- Definition

Title of a 12(b) registered security.

+ References

Reference 1: http://www.xbrl.org/2003/role/presentationRef

-Publisher SEC

-Name Exchange Act

-Number 240

-Section 12

-Subsection b

+ Details

Name:

dei_Security12bTitle

Namespace Prefix:

dei_

Data Type:

dei:securityTitleItemType

Balance Type:

Period Type:

duration

- Definition

Name of the Exchange on which a security is registered.

+ References

Reference 1: http://www.xbrl.org/2003/role/presentationRef

-Publisher SEC

-Name Exchange Act

-Number 240

-Section 12

-Subsection d1-1

+ Details

Name:

dei_SecurityExchangeName

Namespace Prefix:

dei_

Data Type:

dei:edgarExchangeCodeItemType

Balance Type:

Period Type:

duration

- Definition

Boolean flag that is true when the Form 8-K filing is intended to satisfy the filing obligation of the registrant as soliciting material pursuant to Rule 14a-12 under the Exchange Act.

+ References

Reference 1: http://www.xbrl.org/2003/role/presentationRef

-Publisher SEC

-Name Exchange Act

-Number 240

-Section 14a

-Subsection 12

+ Details

Name:

dei_SolicitingMaterial

Namespace Prefix:

dei_

Data Type:

xbrli:booleanItemType

Balance Type:

Period Type:

duration

- Definition

Trading symbol of an instrument as listed on an exchange.

+ References

No definition available.

+ Details

Name:

dei_TradingSymbol

Namespace Prefix:

dei_

Data Type:

dei:tradingSymbolItemType

Balance Type:

Period Type:

duration

- Definition

Boolean flag that is true when the Form 8-K filing is intended to satisfy the filing obligation of the registrant as written communications pursuant to Rule 425 under the Securities Act.

+ References

Reference 1: http://www.xbrl.org/2003/role/presentationRef

-Publisher SEC

-Name Securities Act

-Number 230

-Section 425

+ Details

Name:

dei_WrittenCommunications

Namespace Prefix:

dei_

Data Type:

xbrli:booleanItemType

Balance Type:

Period Type:

duration

- Details

Name:

us-gaap_StatementClassOfStockAxis=upld_CommonStockParValue00001PerShareMember

Namespace Prefix:

Data Type:

Balance Type:

Period Type:

- Details

Name:

us-gaap_StatementClassOfStockAxis=upld_PreferredStockPurchaseRightsMember

Namespace Prefix:

Data Type:

Balance Type:

Period Type: