What changed in this filing

/stocks — the workspaceLOADING

Item 8. Financial Statements and Supplementary Data

2025-03-12 compared with 2024-02-22 · 195 added, 258 removed, 964 unchanged (32% of the section changed)

16 unchanged sentences

generally accepted accounting principles.

We also have audited, in accordance with the standards of the Public Company Accounting Oversight Board (United States) (PCAOB), the Company's internal control over financial reporting as of December 31, 2023, based on criteria established in Internal Control—Integrated Framework issued by the Committee of Sponsoring Organizations of the Treadway Commission (2013 framework), and our report dated February 22, 2024, expressed an unqualified opinion thereon.

We also have audited, in accordance with the standards of the Public Company Accounting Oversight Board (United States) (PCAOB), the Company's internal control over financial reporting as of December 31, 2024, based on criteria established in Internal Control—Integrated Framework issued by the Committee of Sponsoring Organizations of the Treadway Commission (2013 framework), and our report dated March 12, 2025 expressed an unqualified opinion thereon.

Basis for Opinion

19 unchanged sentences

As described in Note 5 to the consolidated financial statements, the Company recorded a goodwill impairment charge of $87 million during the year ended December 31, 2024.

Auditing management’s goodwill impairment assessment was complex and required auditor judgment because the estimation of fair values involves subjective management assumptions, including estimation of future cash flows, the long-term rate of growth for the Company’s business and weighted average cost of capital.

Auditing management’s goodwill impairment assessment was complex and required auditor judgment because the estimation of fair values involves subjective management assumptions, including estimation of future operating margins, projected revenue growth rates and weighted average cost of capital.

Assumptions used in these valuation models are forward-looking, and changes in these assumptions can have a material effect on the determination of fair value.

How We Addressed the Matter in Our Audit

We obtained an understanding, evaluated the design, and tested the operating effectiveness of certain controls over the Company’s impairment assessment process, including controls over management’s review of the valuation models and its determination of the significant assumptions described above.

To test the Company’s impairment evaluation, our audit procedures included, among others, assessing the valuation methodologies and testing the significant assumptions discussed above and the underlying data used by the Company in its evaluation.

5 unchanged sentences

Austin, Texas

February 22, 2024

March 12, 2025

Upland Software, Inc.

3 unchanged sentences

Cash and cash equivalents $ 56,426 $ 236,559

Restricted cash 626 —

Accounts receivable, net of allowance for credit losses 38,647 38,765

19 unchanged sentences

Deferred revenue 93,706 102,763

Liabilities due to sellers of businesses — 5,429

Operating lease liabilities, current 1,000 2,351

8 unchanged sentences

Total liabilities 424,597 626,092

Mezzanine Equity:

Series A Convertible Preferred stock, 0.0001 par value;

4 unchanged sentences

Common stock, $ 0.0001 par value;

75,000,000 and 50,000,000 shares authorized as of December 31, 2023 and December 31, 2022, respectively;

75,000,000 shares authorized as of December 31, 2024 and December 31, 2023, respectively;

28,168,267 and 29,908,407 shares issued and outstanding as of December 31, 2024 and December 31, 2023, respectively

Additional paid-in capital 605,286 608,995

Accumulated other comprehensive income

Accumulated other comprehensive (loss) income ( 21,990 ) 6,168

Accumulated deficit ( 601,604 ) ( 488,872 )

Total stockholders’ equity 126,294 308,870

Total liabilities, convertible preferred stock and stockholders’ equity $ 870,024 $ 1,113,459

Total stockholders’ (deficit) equity ( 18,305 ) 126,294

Total liabilities, convertible preferred stock and stockholders’ (deficit) equity $ 529,522 $ 870,024

See accompanying notes.

27 unchanged sentences

Total other expense ( 7,797 ) ( 18,448 ) ( 29,926 )

Loss before benefit from income taxes ( 182,367 ) ( 70,154 ) ( 66,556 )

Benefit from income taxes 2,493 1,741 8,344

Loss before benefit from (provision for) income taxes ( 110,092 ) ( 182,367 ) ( 70,154 )

Benefit from (provision for) income taxes ( 2,640 ) 2,493 1,741

Net loss $ ( 112,732 ) $ ( 179,874 ) $ ( 68,413 )

31 unchanged sentences

Balance at December 31, 2021 — — 31,096,548 $ 3 $ 568,384 $ ( 11,514 ) $ ( 240,585 ) $ 316,288

Issuance of Convertible Preferred Stock 115,000 110,445 — — — — — —

Dividends accrued - Convertible Preferred Stock — 1,846 — — ( 1,846 ) — — ( 1,846 )

Issuance of stock under Company plans, net of shares withheld for tax — — 1,125,307 — ( 1,385 ) — — ( 1,385 )

5 unchanged sentences

Balance at December 31, 2022 115,000 $ 112,291 32,221,855 $ 3 $ 606,755 $ 11,110 $ ( 308,998 ) $ 308,870

Issuance of Convertible Preferred Stock 115,000 $ 110,445 — — — — — —

Dividends accrued - Convertible Preferred Stock — 5,347 — — ( 5,347 ) — — ( 5,347 )

Issuance of stock under Company plans, net of shares withheld for tax — — 931,652 — ( 1,086 ) — — ( 1,086 )

Stock repurchases and retirements — ( 3,245,100 ) — ( 14,201 ) ( 14,201 )

Stock-based compensation — — — — 22,874 — — 22,874

Foreign currency translation adjustment — — 2,685 2,685

Unrealized translation loss on intercompany loans with foreign subsidiaries — — ( 9,978 ) ( 9,978 )

Unrealized translation gain on intercompany loans with foreign subsidiaries — — 4,096 4,096

Interest rate swaps — — ( 11,723 ) ( 11,723 )

30 unchanged sentences

Prepaid expenses and other current assets 74 ( 471 ) 10,070

Other assets 10,866 ( 12,811 ) ( 13,260 )

Interest rate swaps and other assets ( 10,089 ) 10,866 ( 12,811 )

Accounts payable 1,344 ( 6,896 ) ( 7,175 )

7 unchanged sentences

Financing activities

Payments on finance leases — — ( 12 )

Payments of debt costs ( 358 ) ( 221 ) ( 203 )

5 unchanged sentences

Additional consideration paid to sellers of businesses — ( 5,617 ) ( 9,306 )

Net cash provided by (used in) financing activities ( 61,384 ) 94,151 ( 8,180 )

Effect of exchange rate fluctuations on cash 567 ( 1,413 ) ( 897 )

Change in cash and cash equivalents ( 12,094 ) 59,495 ( 60,871 )

Cash and cash equivalents, beginning of period 248,653 189,158 250,029

Cash and cash equivalents, end of period $ 236,559 $ 248,653 $ 189,158

Net cash used in financing activities ( 202,307 ) ( 61,384 ) 94,151

Effect of exchange rate fluctuations on cash, cash equivalents and restricted cash ( 557 ) 567 ( 1,413 )

Change in cash, cash equivalents and restricted cash ( 179,507 ) ( 12,094 ) 59,495

Cash, cash equivalents and restricted cash, beginning of period 236,559 248,653 189,158

Cash, cash equivalents and restricted cash, end of period $ 57,052 $ 236,559 $ 248,653

Supplemental disclosures of cash flow information:

9 unchanged sentences

Upland Software, Inc.

(“Upland,” “we,” “us,” “our,” or the “Company”), a Delaware corporation, is a provider of cloud-based software that enables organizations to plan, manage and execute projects and work.

Upland’s cloud offerings address a broad range of software needs, from strategic planning to task execution in the following functional areas:

Sales, Marketing, Contact Center, Knowledge Management, Project Management, Information Technology, Business Operations, and Human Resources and Legal.

To support continued growth, Upland intends to pursue acquisitions within its cloud offerings of complementary technologies and businesses.

Upland expects that this will expand its product offerings, customer base and market access, resulting in increased benefits of scale.

Consistent with Upland’s growth strategy, Upland has made a total of 31 acquisitions in the 12 years ended December 31, 2023.

(“Upland,” “we,” “us,” “our,” or the “Company”), a Delaware corporation,enables global businesses to work smarter with over 20 proven cloud software products that increase revenue, reduce costs, and deliver immediate value.

Upland's AI-powered solutions cover knowledge management, content lifecycle and workflow automation, and digital marketing..

Upland’s powerful cloud products are trusted by more than 10,000 customers ranging from large global corporations and various government agencies to small and medium-sized businesses.

The Company's customers operate in a wide variety of industries, including financial services, consulting services, technology, manufacturing, media, telecommunications, government, insurance, non-profit, healthcare, life sciences, retail, and hospitality.

Through a series of acquisitions and integrations, the Company has established a library of diverse software applications under the Upland brand that address specific digital transformation needs.

In addition to its strategy to increase core organic growth, Upland may pursue acquisitions within its cloud offerings of complementary technologies and businesses.

Basis of Presentation and Summary of Significant Accounting Policies

10 unchanged sentences

however, actual results could differ from those estimates.

Upland is not aware of any specific event or circumstance that would require an update to its estimates or judgments or a revision of the carrying value of its assets or liabilities as of February 22, 2024, the date of issuance of this Annual Report on Form 10-K.

Upland is not aware of any specific event or circumstance that would require an update to its estimates or judgments or a revision of the carrying value of its assets or liabilities as of March 12, 2025, the date of issuance of this Annual Report on Form 10-K.

These estimates may change as new events occur and additional information is obtained.

3 unchanged sentences

Cash equivalents are stated at cost, which approximates market value, because of the short maturity of these instruments.

Restricted Cash

The Company is required to maintain a letter of credit as collateral during the term of an operating lease for office space.

As of December 31, 2024, we had $ 0.6 million of restricted cash deposited in a restricted account as collateral for the letter of credit.

The Company had no restricted cash as of December 31, 2023.

The following table provides a reconciliation of cash, cash equivalents and restricted cash reported within the consolidated balance sheets that sum to the total of the same amounts shown in the consolidated statements of cash flows (in thousands):

As of December 31,

Cash and cash equivalents $ 56,426 $ 236,559

Restricted cash 626 —

Total cash, cash equivalents and restricted cash $ 57,052 $ 236,559

Accounts Receivable and Allowance for Credit Losses

31 unchanged sentences

Business Combinations

We apply the provisions of Financial Accounting Standards Board (“FASB”) Accounting Standards Codification (“ASC”) 805, Business Combinations , in accounting for our acquisitions which requires the acquisition purchase price to be allocated to the tangible and intangible assets acquired and liabilities assumed based on their estimated fair values at the acquisition dates.

to the tangible and intangible assets acquired and liabilities assumed based on their estimated fair values at the acquisition dates.

The excess of the purchase price over these estimated fair values is recorded to goodwill.

22 unchanged sentences

See “ Note 5.

Goodwill and Other Intangible Assets” f or more information regarding our 2023 and 2022 Goodwill impairments.

Goodwill and Other Intangible Assets” f or more information regarding our historical goodwill impairments.

Identifiable intangible assets consist of customer relationships, marketing-related intangible assets and developed technology.

5 unchanged sentences

The Company evaluates the recoverability of intangible assets by comparing their carrying amounts to the future net undiscounted cash flows expected to be generated by the intangible assets.

If such intangible assets are considered to be impaired, the impairment to be recognized is measured as the amount by which the carrying amount of the intangible assets exceeds the fair value of the assets.

If such intangible assets are considered to be

impaired, the impairment to be recognized is measured as the amount by which the carrying amount of the intangible assets exceeds the fair value of the assets.

Long-Lived Assets

3 unchanged sentences

Assets to be disposed of are reported at the lower of the carrying value or net realizable value.

No indicators of impairment were identified during the years ended December 31, 2023, 2022 or 2021.

No indicators of impairment of long-lived assets were identified during the years ended December 31, 2024, 2023 or 2022.

Software Development Costs

20 unchanged sentences

In 2024 and 2023, the Company had no write offs of debt issuance costs.

In 2019, the Company entered into floating-to-fixed interest rate swap agreements to limit exposure to interest rate risk related to our debt.

Until the termination of a portion of the interest rate swaps as described in “ Note 7.

Debt” , these interest rate swaps effectively converted $ 258.5 million and $ 522.5 million of our term loans as of December 31, 2023 and 2022, respectively, from variable interest payments to fixed interest rate payments, based on an annualized fixed rate of 5.4 %, for the remaining term of the debt.

In 2019, the Company entered into floating-to-fixed interest rate swap agreements to limit exposure to interest rate risk related to our variable rate debt.

ASC 815, Derivatives and Hedging , requires entities to recognize derivative instruments as either assets or liabilities in the statement of financial position at fair value.

The accounting for changes in the fair value (i.e., gains or losses) of a derivative instrument depends on whether it has been designated and qualifies as part of a hedging relationship and, further, on the type of hedging relationship.

The Company assessed the effectiveness of the hedging relationship under the hypothetical derivative method and noted that all of the critical terms of the hypothetical derivative and hedging instrument were the same.

The hedging relationship continues to limit the Company’s exposure to the variability in interest rates under the Company’s term loans and related cash outflows.

As such, the Company has deemed this hedging relationship as highly effective in offsetting cash flows attributable to hedged risk (variability in forecasted monthly interest payments) for the term of the term loans and interest rate swap agreements.

All derivative financial instruments are recorded at fair value as a net asset or liability on our consolidated balance sheets.

As of December 31, 2023, the fair value of interest rate swaps included in Interest rate swap assets on our consolidated balance sheets was $ 14.3 million.

As of December 31, 2022, the fair value of interest rate swaps included in Interest rate swap assets was $ 41.2 million.

The change in the fair value of the hedging instruments is recorded in Interest Rate Swaps on our consolidated stateme nts of comprehensive loss.

Amounts deferred on interest rate swaps in our consolidated statements of comprehensive income will be reclassified to Interest expense, net on our consolidated statements of operations in the period in which the hedged item affects earnings.

Cash flows from hedging instruments are classified in the same category as the cash flows for the underlying item being hedged within "Net cash provided by operating activities" on the consolidated statements of cash flows.

The accounting for changes in the fair value of a derivative instrument depends on whether it has been designated and qualifies as part of a hedging relationship and, further, on the type of hedging relationship.

Prior to August 2024, the Company had determined the interest rate swaps qualified for designation as cash flow hedges and recorded the changes in their fair value on our consolidated statements of comprehensive loss.

In August 2024, in conjunction with the prepayment of a portion of the Company’s debt, the Company de-designated its interest rate swaps and as a result, under the accounting guidance, changes in the fair value of the interest rate swaps after that date are recorded in interest expense, net in the consolidated statements of operations.

Amounts deferred on interest rate swaps in our consolidated statements of comprehensive loss will be reclassified to Interest expense, net on our consolidated statements of operations in the period in which the hedged item affects earnings.

flows from the interest rate swaps are classified in the same category as the cash flows for the underlying item being hedged within "Net cash provided by operating activities" on the consolidated statements of cash flows.

Fair Value of Financial Instruments

10 unchanged sentences

See “ Note 12.

Series A Convertible Preferred Stock—Series A Convertible Preferred Stock” for further details.

Mezzanine Equity —Series A Convertible Preferred Stock” for further details.

The Series A Preferred Stock and cumulative preferred dividends, net of preferred issuance costs, is presented as mezzanine equity of $ 123.2 million as of December 31, 2024 in the Company’s consolidated balance sheets.

The Series A Preferred Stock is classified as mezzanine equity because it is redeemable at the option of its holders (upon a deemed liquidation event as defined in “ Note 12.

Series A Convertible Preferred Stock—Series A Convertible Preferred Stock—Deemed Liquidation Event Redemption” ) and has a condition for redemption that is not solely within the control of the issuer.

Mezzanine Equity —Series A Convertible Preferred Stock—Deemed Liquidation Event Redemption” ) and has a condition for redemption that is not solely within the control of the issuer.

Revenue Recognition

26 unchanged sentences

ROU assets represent the Company's right to use an underlying asset for the lease term and the corresponding lease liabilities represent its obligation to make lease payments arising from the lease.

Lease ROU assets and lease liabilities are recognized based on the present value of the future minimum lease payments over the lease term at commencement date.

Lease ROU assets and lease liabilities are recognized based on the present value of the future minimum lease payment over the lease term at commencement date.

The lease ROU asset includes any initial direct costs incurred and is reduced for any tenant incentives.

As the Company’s leases do not provide an implicit rate, the net present value of future minimum lease payments is determined using the Company’s incremental borrowing rate.

The Company’s lease terms may include options to extend or terminate the lease when it is reasonably certain the Company will exercise that option.

Lease expense for minimum lease payments is recognized on a straight-line basis over the lease term.

The Company does not record short term leases with an initial lease term of one year or less on the consolidated balance sheets.

As the Company’s leases do not provide an implicit rate, the net present value of future minimum lease payments is determined using the Company’s incremental borrowing rate.

Stock-Based Compensation

We measure all share-based payments, including grants of options to purchase common stock and the issuance of restricted stock or restricted stock units to employees, service providers and board members, using the fair-value at grant date.

We record forfeitures as they occur.

The cost of services received from employees and non-employees in exchange for awards of equity instruments is recognized on our consolidated statement of operations based on the estimated fair value of those awards on the grant date and amortized on a straight-line basis over the requisite service period.

We value restricted stock and restricted stock units at the closing price of our common stock on the grant date.

The cost of services received from employees and non-employees in exchange for awards of equity instruments is recognized in our consolidated statement of operations based on the estimated fair value of those awards on the grant date and amortized on a straight-line basis over the requisite service period.

We value restricted stock units at the closing price of our common stock on the grant date.

We value stock option awards using the Black-Scholes option-pricing model.

For the years ended December 31, 2023, 2022 and 2021, stock-based compensation awards consisted primarily of restricted stock and restricted stock units.

From time to time, we grant restricted stock units that also include performance or market-based conditions (“PRSUs”).

For PRSUs granted with a market condition, we use a Monte Carlo simulation analysis to value the award.

Compensation expense for awards with marked-based conditions is recognized over the required service period of the grant based on the grant date fair value of the award and is not subject to fluctuation due to achievement of the underlying market-based condition.

Compensation expense for awards with marked-based conditions is recognized over the requisite service period of the grant based on the grant date fair value of the award and is not subject to fluctuation due to achievement of the underlying market-based condition.

We record forfeitures as they occur.

Comprehensive Income (Loss)

The Company utilizes the guidance in ASC 220, Income Statement—Reporting Comprehensive Income , for the reporting and display of comprehensive income (loss) and its components in the consolidated financial statements.

Comprehensive income (loss) consists of net loss, foreign currency translation adjustments for subsidiaries with functional currencies other than the United States dollar (“USD”), unrealized translation gains (losses) on foreign currency denominated intercompany loans, and unrealized gains (losses) on interest rate swaps.

Refer to “ Note 13.

6 unchanged sentences

Assets and liabilities denominated in currencies other than the functional currency are remeasured using the current exchange rate for monetary accounts and historical exchange rates for non-monetary accounts, with exchange differences on remeasurement included in other expense, net in the accompanying statements of operations.

For the years ended December 31, 2023, 2022 and 2021, net gains of $ 0.3 million, net losses of $ 1.0 million and net gains of $ 48.6 thousand, respectively, were recorded in Other expense, net on our consolidated statements of operations, related to remeasurement of foreign currency transactions.

For the years ended December 31, 2024, 2023 and 2022, net gains of $ 1.1 million, $ 0.3 million and a net loss of $ 1.0 million, respectively, were recorded in Other expense, net on our consolidated statements of operations, related to remeasurement of foreign currency transactions.

We have foreign currency denominated intercompany loans that were used to fund the acquisition of foreign subsidiaries.

Due to the long-term nature of the loans, the foreign currency gains (losses) resulting from remeasurement are recognized as a separate component of the Company’s consolidated statements of stockholders' equity in accumulated other comprehensive loss.

During the years ended December 31, 2023, 2022 and 2021, a translation gain of $ 4.1 million, loss of $ 10.0 million, and loss of $ 0.6 million, respectively, were recognized as a component of accumulated other comprehensive income (loss) in the Company’s statements of stockholders’ equity, related to long-term intercompany loans.

During the years ended December 31, 2024, 2023 and 2022, a translation loss of $ 3.1 million, a translation gain of

$ 4.1 million, and a translation loss $ 10.0 million, respectively, were recognized as a component of accumulated other comprehensive income (loss) in the Company’s statements of stockholders’ equity, related to long-term intercompany loans.

Recent Accounting Pronouncements

Recently issued accounting pronouncements - Adopted

In March 2020, the Financial Standards Accounting Board (“FASB”) issued accounting standards update (“ASU”) 2020-04, Reference Rate Reform (Topic 848):

Facilitation of the Effects of Reference Rate Reform on Financial Reporting, which provides optional guidance for a limited time to ease the potential burden in accounting for reference rate reform.

The new guidance provides optional expedients and exceptions for applying GAAP to contracts, hedging relationships and other transactions affected by reference rate reform if certain criteria are met.

The amendments apply only to contracts and hedging relationships that reference the London Interbank Offer Rate (“LIBOR”) or another reference rate expected to be discontinued due to reference rate reform.

These amendments are effective immediately and may be applied prospectively to contract modifications made and hedging relationships entered into or evaluated on or before December 31, 2022.

We adopted ASU 2020-04 during the first quarter of 2023.

On February 21, 2023, the Company entered into an amended and restated credit agreement to, among other things, provide for the replacement of LIBOR with the Secured Overnight Financing Rate (“SOFR”), an index measuring the cost of borrowing cash overnight collateralized by Treasury securities.

The Company elected to apply the debt agreement modification expedients related to changes to the reference rate from LIBOR to SOFR in the Company's Credit Agreement, which it completed during the three months ended March 31, 2023.

Application of these expedients allowed the Company to account for the modification as not substantial.

As a result, the debt agreement modification was accounted for by prospectively adjusting the Credit Agreement’s effective interest rate, any existing unamortized debt discount was carried forward and continued to be amortized and no remeasurement of the Credit Agreement at the modification date was required.

The Company has also elected to apply the hedge accounting expedients and exceptions related to changes to the reference rate from LIBOR to SOFR in the Company's interest rate swaps, which it completed during the three months ended March 31, 2023.

Application of these exceptions preserves the cash flow hedge designation of the interest rate swaps and the related accounting and presentation consistent with past presentation.

The replacement of LIBOR with SOFR in the credit agreement did not have a material impact on the Company’s consolidated financial statements and related disclosures.

See “ Note—7.

Debt ” for additional information.

In August 2020, the FASB issued accounting standards update ASU 2020-06, “Debt—Debt with Conversion and Other Options (Subtopic 470-20) and Derivatives and Hedging—Contracts in Entity’s Own Equity (Subtopic 815-40):

Accounting for Convertible Instruments and Contracts in an Entity’s Own Equity (the “ASU 2020-06).

ASU 2020-06 simplifies the accounting for convertible instruments by reducing the number of accounting models available for convertible debt instruments and convertible preferred stock.

This update also amends the guidance for the derivatives scope exception for contracts in an entity’s own equity to reduce form-over-substance-based accounting conclusions.

ASU 2020-06 amends the diluted earnings per share guidance, including the requirement to use the if-converted method for all convertible instruments.

The update also requires entities to provide expanded disclosures about the terms and features of convertible instruments, how the instruments have been reported in the entity’s financial statements, and information about events, conditions, and circumstances that can affect how to assess the amount or timing of an entity’s future cash flows related to those instruments.

The guidance is effective for interim and annual periods beginning after December 15, 2021.

The Company adopted this guidance in the first quarter of fiscal 2022 with an immaterial impact to the consolidated financial statements.

In October 2021, the FASB issued ASU 2021-08, Business Combinations (Topic 805):

Accounting for Contract Assets and Contract Liabilities from Contracts with Customers , which creates an exception to the general recognition and measurement principle for contract assets and contract liabilities from contracts with customers acquired in a business combination.

The new guidance will require companies to apply the definition of a performance obligation under ASC Topic 606 to recognize and measure contract assets and contract liabilities (i.e., deferred revenue) relating to contracts with customers that are acquired in a business combination.

Under current GAAP, an acquirer in a business combination is generally required to recognize and measure the assets it acquires and the liabilities it assumes at fair value on the acquisition date.

The new guidance will result in the acquirer recording acquired contract assets and liabilities on the same basis that would have been recorded by the acquiree before the acquisition under ASC Topic 606.

These amendments are effective for fiscal years beginning after December 15, 2022 , with early adoption permitted.

We adopted ASU 2021-08 on January 1, 2023 and our adoption did not have a material impact on our consolidated financial statements.

Recently issued accounting pronouncements - Not Adopted

In November 2023, the FASB issued ASU 2023-07, Segment Reporting (Topic 280):

In November 2023, the Financial Standards Accounting Board (“FASB”) issued accounting standards update (“ASU”) 2023-07, Segment Reporting (Topic 280):

Improvements to Reportable Segment Disclosures , which requires public entities to disclose information about their reportable segments' significant expenses and other segment items on an interim and annual basis.

1 unchanged sentence

ASU 2023-07 is effective for fiscal years beginning after December 15, 2023, and for interim periods within fiscal years beginning after December 15, 2024, with early adoption permitted.

The Company is currently evaluating the impact of adopting ASU 2023-07.

The Company adopted this ASU for the Annual Report for the year ended December 31, 2024 and there was no material impact on its financial statements.

Recently issued accounting pronouncements - Not Adopted

In November 2024, the FASB, issued ASU 2024-04, Debt-Debt with Conversions and Other Options .

ASU 2024-04 is intended to clarify requirements for determining whether certain settlements of convertible debt instruments, including convertible debt instruments with cash conversion features or convertible debt instruments that are not currently convertible, should be accounted for as an induced conversion.

This ASU is effective for all entities for annual reporting periods beginning after December 15, 2025, and interim reporting periods within those annual reporting periods, with early adoption permitted.

The Company is currently evaluating the potential impact of this guidance on its disclosures.

In November 2024, the FASB, issued ASU 2024-03, Income Statement-Reporting Comprehensive Income-Expense Disaggregation Disclosures .

ASU 2024-03 is intended to improve disclosures about a public business entity’s expense and provide more detailed information to investors about the types of expenses in commonly presented expense captions.

This ASU is effective for public companies with annual periods beginning after December 15, 2026, and interim reporting periods beginning after December 15, 2027, with early adoption permitted.

The Company is currently evaluating the effects of adoption of this guidance will have on its consolidated financial statements.

In December 2023, the FASB issued ASU 2023-09, Income Taxes (Topic 740):

5 unchanged sentences

2022 Acquisitions

The Company had no acquisitions during the year ended December 31, 2023.

2022 Acquisitions

Acquisitions completed during the year ended December 31, 2022 include the following:

• BA Insight - On February 22, 2022, the Company entered into an agreement to purchase the shares comprising the entire issued share capital of BA Insight Inc., (“BA Insight”), a cloud-based enterprise knowledge management solution.

• Objectif Lune - On January 07, 2022, the Company entered into an agreement to purchase the shares comprising the entire issued share capital of Objectif Lune Inc., a Quebec proprietary company (“Objectif Lune”), cloud-based document workflow product.

2021 Acquisitions

Acquisitions completed during the year ended December 31, 2021 include the following:

• Panviva - On June 24, 2021, the Company entered into an agreement to purchase the shares comprising the entire issued share capital of Panviva Pty Ltd, an Australian proprietary company (“Panviva”), a cloud-based enterprise knowledge management solution.

• BlueVenn - On February 28, 2021 the Company entered into an agreement to purchase the shares comprising the entire issued share capital of BlueVenn Group Limited, a company limited by shares organized and existing under the laws of England and Wales (“BlueVenn”), a cloud-based customer data platform.

• Second Street - On January 19, 2021, the Company entered into an agreement to purchase the shares comprising the entire issued share capital of Second Street Media, Inc., a Missouri corporation (“Second Street”), an audience engagement platform.

document workflow product.

Consideration

The following table summarizes the consideration transferred for the acquisitions described above (in thousands):

BA Insight Objectif Lune Panviva BlueVenn Second Street

BA Insight Objectif Lune

Cash $ 33,355 $ 29,750

645 5,250 3,517 2,429 5,000

Contingent consideration (2)

— — — 2,535 1,650

Working capital and other adjustments

1,587 644 379 ( 537 ) ( 1,365 )

Total consideration $ 35,587 $ 35,644

(1) Represents cash holdbacks subject to indemnification claims that are payable 12 months from closing for Objectif Lune, Panviva, and Second Street, 15 months following closing for BA Insight and 18 months following the closing of BlueVenn.

(1) Represents cash holdbacks subject to indemnification claims that are payable 12 months from closing for Objectif Lune, and 15 months following closing for BA Insight.

As of December 31, 2024, all of the holdbacks had been paid.

(2) Represents the acquisition date fair value of anticipated earnout payments which are based on the estimated probability of attainment of the underlying future performance-based conditions at the time of acquisition.

The maximum potential payout for the BlueVenn and Second Street were $ 21.7 million and $ 3.0 million, respectively.

As of March 31, 2022, the earnout payments for BlueVenn and Second Street were finalized resulting in no payments made.

Refer to “ Note 4.

Fair Value Measurements ” for further discussion regarding the calculation of fair value of acquisition related earnouts and subsequent payouts.

Fair Value of Assets Acquired and Liabilities Assumed

The Company recorded the purchase of the acquisitions described above using the acquisition method of accounting, and has recognized the assets acquired and liabilities assumed at their fair values as of the date of the acquisition.

The following condensed table presents the finalized acquisition-date fair value of the assets acquired and liabilities assumed for the acquisitions closed in 2022 and 2021 (in thousands):

BA Insight Objectif Lune Panviva BlueVenn Second Street

The following condensed table presents the finalized acquisition-date fair value of the assets acquired and liabilities assumed for the acquisitions closed in 2022 (in thousands):

BA Insight Objectif Lune

Year Acquired 2022 2022

34 unchanged sentences

Goodwill deductible for tax purposes related to the above acquisitions was $ 4.6 million.

Total transaction costs incurred with respect to acquisition activity in the years ended December 31, 2023, 2022 and 2021 were nil , $ 4.6 million and $ 6.6 million, respectively.

Total transaction costs incurred with respect to acquisition activity in the years ended December 31, 2024, 2023 and 2022 were nil , nil and $ 4.6 million, respectively.

These costs are included in Acquisition-related expenses on our consolidated statement of operations.

24 unchanged sentences

Balance at December 31, 2022 $ 477,043

Acquired in business combinations 48,768

Adjustment related to prior year business combinations

Adjustment related to finalization of current year business combinations 109

Adjustment related to finalization of business combinations 415

Impairment of goodwill

1 unchanged sentence

Balance at December 31, 2023 $ 353,778

Adjustment related to prior year business combinations 415

Impairment of goodwill

1 unchanged sentence

Balance at December 31, 2024 $ 260,976

We performed a qualitative annual goodwill impairment test in October 2023 and concluded there was no impairment of Goodwill.

As a result of the decline of our stock price impacting our market capitalization during the quarters ended March 31, 2023 and December 31, 2022, we performed quantitative impairment evaluations, which resulted in a goodwill impairments of $ 128.8 million and $ 12.5 million during the quarters ended March 31, 2023 and December 31, 2022, respectively.

We review goodwill for impairment annually in the fourth quarter of the fiscal year and whenever events or changes in circumstances indicate that the carrying value of goodwill might not be recoverable.

As a result of the decline of our stock price impacting our market capitalization during the quarters ended March 31, 2024, March 31, 2023 and December 31, 2022, we performed quantitative impairment evaluations, which resulted in goodwill impairments of $ 87.2 million, $ 128.8 million and $ 12.5 million during the quarters ended March 31, 2024, March 31, 2023 and December 31, 2022, respectively.

Our quantitative goodwill impairment analysis applied two methodologies to estimate the Company’s fair value which were:

3 unchanged sentences

Under the guideline public company method, we estimate fair value based on a market multiple of revenues and earnings derived for comparable publicly traded companies with similar operating characteristics as the Company.

We did not record a goodwill impairment charge for the year ended December 31, 2021.

Intangible assets, net, include the estimated acquisition-date fair values of customer relationships, marketing-related assets and developed technology that the Company recorded as part of its business acquisitions purchases and from acquisitions of customer relationships.

33 unchanged sentences

2025 $ 38,002

Thereafter 5,708

Total $ 123,903

20 unchanged sentences

$ 138.8 million of the U.S.

federal net operating loss carryforwards are related to year prior to 2018 and begin to expire in 2024.

federal net operating loss carryforwards are related to years prior to 2018 and begin to expire in 2025.

The remaining $ 61.9 million carryforward indefinitely.

In addition, $ 43.9 million of foreign net operating loss carryforwards carry forward indefinitely, and the remainder will expire beginning in 2041.

In addition, as of December 31, 2023, the Company had research and development credit carryforwards of approximately $ 4.0 million which will expire beginning in 2024, if not utilized.

Utilization of the U.S.

15 unchanged sentences

Lease liability 453 960 2,139

Unrealized losses — — 1,974

Research and development expenses 19,402 13,247 6,243

12 unchanged sentences

Net deferred taxes $ ( 11,002 ) $ ( 15,970 ) $ ( 18,416 )

Due to the uncertainty surrounding the timing of realizing the benefits of its favorable tax attributes in future tax returns, the Company has placed a valuation allowance against its net deferred tax assets, exclusive of goodwill.

During the year ended December 31, 2023, the valuation allowance increased by $ 20.8 million and during the year ended December 31, 2022 the valuation allowance decreased by $ 8.1 million.

The valuation allowance for the year ended December 31, 2023 increased $ 7.1 million due to the tax effect of items recorded in other comprehensive income with the remaining increase of $ 13.7 million related primarily to current U.S., U.K.

During the year ended December 31, 2024, the valuation allowance increased by $ 9.1 million and during the year ended December 31, 2023 the valuation allowance increased by $ 20.8 million.

The valuation allowance for the year ended December 31, 2024 increased $ 10.1 million related primarily to current U.S., U.K.

and Australia operations, which have current year losses.

The valuation allowance for the year ended December 31, 2022 decreased by $ 13.0 million due to the tax effect of items recorded in other comprehensive income which is partially offset with the remaining increase of approximately $ 4.9 million related primarily to current operations.

This increase was offset by a decrease of $ 1.0 million due to the tax effect of items recorded in other comprehensive income .

The valuation allowance for the year ended December 31, 2023 decreased by $ 20.8 million due to the tax effect of $ 7.1 million of items recorded in other comprehensive income with the remaining increase of approximately $ 13.7 million related primarily to current operations.

At December 31, 2024, we did not provide deferred income taxes on temporary differences resulting from earnings of certain foreign subsidiaries which are indefinitely reinvested.

10 unchanged sentences

Stock compensation ( 1.5 ) % ( 2.2 ) % ( 9.5 ) %

Global intangible low-taxed income ( 2.6 ) % ( 1.3 ) % — %

intercompany dividend 2.5 % — % — %

Disallowed excess executive compensation ( 0.7 ) % — % ( 0.6 ) %

3 unchanged sentences

Change in tax rates — % 0.6 % 2.1 %

Australia tax basis uplift — % — % 2.1 %

( 2.4 ) % 1.4 % 2.5 %

2 unchanged sentences

The Company has determined it has an immaterial exposure related to uncertain tax positions as of December 31, 2024.

The $ 0.8 million exposure at December 31, 2022 was released in 2023 due to a lapse in the statute of limitations for a Canadian exposure.

To the extent the Company is required to recognize interest and penalties related to unrecognized tax liabilities, this amount will be recorded as an accrued liability.

A reconciliation of the beginning and ending amount of unrecognized tax exposure is as follows (in thousands):

Balance at December 31, 2021 $ 772

Additions for tax positions of prior years 45

Balance at December 31, 2022 $ 817

Reductions for tax positions of prior years ( 817 )

Balance at December 31, 2023 $ —

The Company’s assessment of its unrecognized tax benefits is subject to change as a function of the Company’s financial statement audit.

The Company recognizes interest and penalties related to uncertain tax positions in income tax expense.

3 unchanged sentences

The Company is no longer subject to U.S.

federal income tax examinations for years ending before December 31, 2019 and is no longer subject to state and local or foreign income tax examinations by tax authorities for years ending before December 31, 2018.

The Company is not currently under audit for federal, state or any foreign jurisdictions.

US operating losses generated in years prior to 2019 remain open to adjustment until the statute of limitations closes for the tax year in which the net operating losses are utilized.

federal income tax examinations for years ending before December 31, 2020 and is no longer subject to state and local or foreign income tax examinations by tax authorities for years ending before December 31, 2019 US operating losses generated in years prior to 2020 remain open to adjustment until the statute of limitations closes for the tax year in which the net operating losses are utilized.

Long-term debt consisted of the following at December 31, 2024 and December 31, 2023 (in thousands):

4 unchanged sentences

Credit Facility

In 2019, the Company entered into a credit agreement (the “Credit Facility”) which provided for (i) a fully-drawn $ 350 million, 7 year, senior secured term loan facility (the “Term Loan”) and (ii) a term loan facility to be established under the Credit Facility in an aggregate principal amount of $ 190.0 million (the “2019 Incremental Term Loan” and together with the Term Loan, the “Term Loans”) and (iii) a $ 60 million, 5 year, revolving credit facility (the “Revolver”) that was fully available as of December 31, 2023.

Loans under the Revolver are available up to $ 60 million, of which none is currently outstanding.

The Revolver provides a sub facility whereby the Company may request letters of credit (the “Letters of Credit”) in an aggregate amount not to exceed, at any one time outstanding, $ 10.0 million for the Company.

The aggregate amount of outstanding Letters of Credit are reserved against the credit availability under the Maximum Revolver Amount.

The Company incurs a 0.50 % per annum unused line fee on the unborrowed balance of the Revolver which is paid quarterly.

Loans under the Revolver may be borrowed, repaid and reborrowed until August 6, 2024 (the “Maturity Date”), at which time all amounts borrowed under the Revolver must be repaid.

As of December 31, 2023, the Company had no borrowings outstanding under the Revolver or related sub facility.

In 2019, the Company entered into a credit agreement (the “Credit Facility”) which provided for (i) fully-drawn, 7 year, senior secured term loans for $ 350 million and $ 190 million maturing August 6, 2026 (the “Term Loans”) and (ii) a $ 60 million, 5 year, revolving credit facility (the “Revolver”) which matured August 6, 2024.

Payment terms

The Term Loans are repayable on a quarterly basis beginning on December 31, 2019 by an amount equal to 0.25 % ( 1.00 % per annum) of the aggregate principal amount of such loan.

Any amount remaining unpaid is due and payable in full on August 6, 2026 (the “Term Loan Maturity Date”).

Initially, at the option of the Company, the Term Loans (including the 2019 Incremental Term Loan) accrued interest at a per annum rate based on (i) the Base Rate plus a margin of 2.75 % or (ii) the rate (not less than 0.00 %) for Eurodollar deposits quoted on the LIBOR01 or LIBOR02 pages on the Reuters Screen, or as otherwise determined in accordance with the Credit Facility (based on a period equal to 1, 2, 3 or 6 months or, if available and agreed to by all relevant Lenders and the Agent, 12 months or such period of less than 1 month) plus a margin of 3.75 %.

The Base Rate for any day was a rate per annum equal to the greatest of (i) the prime rate in effect on such day, (ii) the federal funds effective rate (not less than 0.00 %) in effect on such day plus ½ of 1.00%, and (ii) the Eurodollar rate for a one month interest period beginning on such day plus 1.00 %.

On February 21, 2023, the Company entered into an amendment to its Credit Facility.

The amendment amended the interest rate benchmark from LIBOR to SOFR.

Other than the foregoing, the material terms of the Credit Agreement remain unchanged.

After giving effect to the interest rate swaps described below, $ 258.5 million of the Term Loans has an effective annualized fixed interest rate of 5.4 %, and the remaining principal outstanding at December 31, 2023 has a floating interest rate of 9.2 %

The Term Loans are repayable on a quarterly basis by an amount equal to 0.25 % ( 1.00 % per annum) of the aggregate principal amount of such loan.

Any amount remaining unpaid is due and payable in full on August 6, 2026.

At the option of the Company, the Term Loans accrue interest at a per annum rate based on (i) the Base Rate (as defined below) plus a margin of 2.75 % or (ii) the Term SOFR Reference Rate plus the Term SOFR Adjustment (not less than 0.00 %) published by CME Group Benchmark Administration Limited (CBA), or as otherwise determined in accordance with the Credit Facility (based on a period equal to 1, 2, 3 or 6 months or, if available and agreed to by all relevant Lenders and the Agent, 12 months or such period of less than 1 month) plus a margin of 3.75 %.

The Base Rate for any day was a rate per annum equal to the greatest of (i) the prime rate in effect on such day, (ii) the Federal Funds Effective Rate (not less than 0.00 %) in effect on such day plus ½ of 1.00%, and (iii) the Federal Funds Effective Rate for a one month interest period beginning on such day plus 1.00 %.

Accrued interest is paid quarterly or, with respect to Term Loans that are accruing interest based on the Federal Funds Effective Rate, at the end of the applicable interest rate period.

At December 31, 2024, the floating interest rate was 8.2 %.

On August 15, 2024, the Company prepaid $ 175.0 million of the Term Loans and from September 30, 2024 through December 31, 2024, the Company prepaid an additional $ 8.0 million in principal payments.

On August 31, 2023, the Company prepaid $ 35.0 million of the Term Loans.

The Revolver matured August 6, 2024.

Loans under the Revolver could be borrowed, repaid and reborrowed until maturity, at which time all amounts borrowed under the Revolver must be repaid.

No amounts were drawn on the Revolver at the time of its maturity.

The Credit Facility contains customary affirmative and negative covenants.

The Term Loan and Revolver are secured by substantially all of the Company's assets.

As of December 31, 2024 the Company was in compliance with all covenants under the Credit Facility.

Interest rate swaps

In 2019, the Company entered into floating-to-fixed interest rate swap agreements to limit exposure to interest rate risk related to our debt.

Until the termination of a portion of the interest rate swaps as described below, these interest rate swaps effectively converted the entire balance of the Company's $ 540.0 million original principal Term Loans from variable interest payments to fixed interest rate payments, based on an annualized fixed rate of 5.4 %, for the 7 -year term of debt.

The interest rate associated with our undrawn $ 60 million Revolver remains floating.

In August 2023, the Company sold $ 259.9 million of the notional amount of its interest rate swap assets back to the counterparties for $ 20.5 million , reducing the total notional amount of the interest rate swap assets to $ 259.9 million .

The $ 20.5 million gain in accumulated other comprehensive income related to the $ 259.9 million amount sold is being released to interest expense, net as interest is accrued on the Company’s variable-rate debt over the remaining term of the Term Loans as a decrease to interest expense, net, the amortization of which totaled $ 2.5 million for the year ended December 31, 2023.

As discussed above, on September 1, 2023, the Company prepaid $ 35.0 million of the Term Loans.

As a result of this prepayment, $ 2.8 million of the deferred gain in accumulated comprehensive income was released immediately into earnings as interest expense, net.

In the next twelve months, the Company estimates that $ 5.9 million will be reclassified from Accumulated other comprehensive income (loss) to Interest expense, net on our consolidated statement of operations.

Amounts reported in accumulated other comprehensive income related to the Company's derivatives are reclassified to interest expense, net as interest is accrued on the Company’s variable-rate debt.

Until the termination of a portion of the interest rate swaps as described below, these interest rate swaps effectively converted the entire balance of the Company's original principal Term Loans from variable interest payments to fixed interest rate payments, based on an annualized fixed rate of 5.4 %, for the term of debt.

In August 2023, the Company sold $ 259.9 million of the notional amount of its interest rate swap assets back to the counterparties for $ 20.5 million .

At that time, a $ 20.5 million gain was recorded in accumulated other comprehensive income related to the notional amount sold.

That gain is being released to interest expense, net as interest is accrued on the Company’s variable-rate debt over the remaining term of the Term Loans as a decrease to interest expense, net.

In August 2024, the Company prepaid $ 175.0 million of the Term Loans resulting in the release of $ 9.0 million of the deferred gain to interest expense , net and from September 30, 2024 through December 31, 2024, the Company prepaid an additional $ 8.0 million in principal payments resulting in the additional release of $ 0.4 million of the deferred gain to interest expense, net.

In August 2023, the Company prepaid $ 35.0 million of the Term Loans.

As a result of this prepayments, $ 2.8 million of the deferred gain in accumulated comprehensive income was released immediately into earnings as interest expense, net in 2023.

In August 2024, the Company de-designated all of the interest rate swaps in conjunction with the August 2024 debt prepayment.

The amount remaining in accumulated other comprehensive loss at the de-designation date was $ 11.4 million and is being amortized to interest expense, net over the effective period of the original interest rate swap agreements.

Subsequent to the de-designation, changes in the fair value of the interest rate swaps are recorded to interest expense, net.

Net change in fair value of the interest rate swaps recognized in interest expense, net for the year ended December 31, 2024 was expense of $ 1.6 million.

Amounts reported in accumulated other comprehensive loss related to the Company's derivatives are reclassified to interest expense, net as interest is accrued on the Company’s variable-rate debt or prepayments on the Term Loans are made.

The impact of the Company’s derivative financial instruments on its consolidated statements of comprehensive loss was as follows (in thousands):

5 unchanged sentences

$ ( 18,786 ) $ ( 11,723 ) $ 49,577

In the next twelve months, assuming no additional prepayments, the Company estimates that $ 6.3 million will be reclassified from Accumulated other comprehensive income (loss) to Interest expense, net on our consolidated statement of operations.

Cash interest costs averaged 6.6 %, 7.2 %, and 5.4 % for the years ended December 31, 2024, 2023, and 2022, respectively.

1 unchanged sentence

These issuance costs will be amortized to Interest expense, net on our consolidated statement of operations, over the term of the Credit Facility.

The Credit Facility contains customary affirmative and negative covenants.

The negative covenants limit the ability of the Loan Parties to, among other things (in each case subject to customary exceptions for a credit facility of this size and type):

• Incur additional indebtedness or guarantee indebtedness of others;

• Create liens on our assets;

• Make investments, including certain acquisitions;

• Enter into mergers or consolidations;

• Dispose of assets;

• Pay dividends and make other distributions on the Company’s capital stock, and redeem and repurchase the Company’s capital stock;

• Enter into transactions with affiliates;

• Prepay indebtedness or make changes to certain agreements.

The Credit Facility has no financial covenants as long as less than 35 % of the Revolver is drawn as of the last day of any fiscal quarter.

If 35 % of the Revolver is drawn as of the last day of a given fiscal quarter, the Company will be required to maintain a Total Leverage Ratio (the ratio of funded indebtedness as of such date less the amount of unrestricted cash and cash equivalents of the Company and its guarantors in an amount not to exceed $ 50.0 million, to Adjusted EBITDA (calculated on a pro forma basis including giving effect to any acquisition)), measured on a quarter-end basis for each four consecutive fiscal quarters then ended, of not greater than 6.00 to 1.00.

The Credit Facility contains customary events of default subject to customary cure periods for certain defaults that include, among others, non-payment defaults, inaccuracy of representations and warranties, covenant defaults, cross-defaults to certain other material indebtedness, change in control, bankruptcy and insolvency defaults and material judgment defaults.

The occurrence of an event of default could result in the acceleration of Term Loans and Revolver and a right by the agent and lenders to exercise remedies.

At the election of the lenders, a default interest rate shall apply on all obligations during an event of default, at a rate per annum equal to 2.00 % above the applicable interest rate.

The Term Loan and Revolver are secured by substantially all of the Company's assets.

As of December 31, 2023 the Company was in compliance with all covenants under the Credit Facility.

Debt Maturities

18 unchanged sentences

Due to the net losses incurred for the years ended December 31, 2024, 2023 and 2022, basic and diluted loss per share were the same, as the effect of all potentially dilutive securities would have been anti-dilutive.

The Company adopted ASU 2020-06 on January 1, 2022 as detailed in “ Note 2.

Basis of Presentation and Summary of Significant Accounting Policies—Recent Accounting Pronouncements—Recently issued accounting pronouncements - Adopted .” As such, the Company is required to use the application of the if-converted method for calculating diluted earnings per share on our Series A Preferred Stock.

The Company applies the treasury stock method for calculating diluted earnings per share on our stock options, restricted stock awards, restricted stock units and performance restricted stock units.

The Company is required to use the application of the if-converted method for calculating diluted earnings per share on our Series A Preferred Stock.

Company applies the treasury stock method for calculating diluted earnings per share on our stock options, restricted stock awards, restricted stock units and performance restricted stock units.

The following table sets forth the anti-dilutive common share equivalents excluded from the weighted-average shares used to calculate diluted net loss per common share:

10 unchanged sentences

The Series A Preferred Stock has a conversion price of $ 17.50 per share, as detailed in “ Note 12.

Series A Convertible Preferred Stock”

Mezzanine Equity —Series A Convertible Preferred Stock”

Operating Leases

The Company leases office space under operating leases that expire between 2024 and 2029.

The Company currently leases office space under operating leases that expire between 2024 and 2029.

The terms of the Company's non-cancelable operating lease arrangements typically contain fixed rent increases over the term of the lease, rent holidays and provide for additional renewal periods.

Rent expense on these operating leases is recognized over the term of the lease on a straight-line basis.

Finance Leases

The current and long-term portion of finance lease obligations are included in Accrued expenses and other current liabilities and Other long-term liabilities line items on the consolidated balance sheet, respectively.

The Company has had no finance lease agreements since December 31, 2021.

Lease Expense

1 unchanged sentence

The $ 2.5 million office rent expense in 2022 includes approximately $ 1.1 million of transformation charges in conjunction with the closures of the BA Insight and Objectif Lune offices as we continue to consolidate and integrate these acquisitions.

The $ 6.2 million office rent expense in 2021 includes approximately $ 4.4 million of transformation charges in conjunction with the closures of the the Panviva, BlueVenn, Second Street and Localytics offices as we continue to consolidate and integrate these acquisitions.

The Company has entered into sublease agreements related to excess office space as a result of the Company's transformation activities related to its acquisitions.

14 unchanged sentences

Operating leases

$ 653 $ 1,943

Weighted average remaining lease term (in years):

4 unchanged sentences

Future minimum payments for operating lease obligations and purchase commitments are as follows (in thousands):

Thereafter 12

Total minimum lease payments 1,876

4 unchanged sentences

Total lease liabilities $ 1,762

Subsequent to December 31, 2024, the Company entered into an operating lease for its new corporate offices in Austin, Texas.

The Company’s existing lease agreement for its corporate office space expires in June 2025.

The new lease term begins in July 2025 and expires in January 2033 with an option to renew the lease for an additional three years .

Total commitments under this lease are approximately $ 1.8 million, net of lease incentives of $ 0.6 million.

Commitments and Contingencies

5 unchanged sentences

2025 $ 16,469

Thereafter 1,754

Total minimum payments $ 20,120

6 unchanged sentences

Gain contingencies related to indemnification claims are not recognized on our consolidated financial statements until realized.

Letter of Credit

In conjunction with a December 2024 operating lease agreement, the Company provided a $ 0.6 million letter of credit in conformance with the contractual provisions of the lease.

The letter of credit expires July 2029.

The amount underlying such letter of credit is reflected as restricted cash in the Company's consolidated balance sheets as of December 31, 2024.

Property and Equipment, Net

5 unchanged sentences

Property and equipment, net $ 1,518 $ 1,932

Amortization of assets recorded under finance leases is included with depreciation expense.

Depreciation and amortization expense on Property and equipment, net was $ 1.4 million, $ 1.5 million and $ 2.0 million for the years ended December 31, 2023, 2022 and 2021, respectively.

Depreciation expense on property and equipment, net was $ 1.2 million, $ 1.4 million and $ 1.5 million for the years ended December 31, 2024, 2023 and 2022, respectively.

The Company recorded no impairment of property and equipment during the years ended December 31, 2024, 2023 and 2022.

During the years ended December 31, 2023, 2022 and 2021, we recognized a $ 47.0 thousand, $ 79.0 thousand and nil losses on disposal of assets related primarily to leasehold improvements associated with the consolidation and integration of prior year acquisitions.

During the years ended December 31, 2024, 2023 and 2022, we recognized $ 17.0 thousand, $ 47.0 thousand and $ 79.0 thousand in losses on disposal of assets related primarily to leasehold improvements associated with the consolidation and integration of prior year acquisitions.

Mezzanine Equity

Series A Convertible Preferred Stock

5 unchanged sentences

Contemporaneous with the Closing Date, the Company and the Purchaser entered into a Registration Rights Agreement (the “Registration Rights Agreement”) and the Company filed a Certificate of Designation (the “Certificate of Designation”) setting out the powers, designations, preferences, and other rights of the Series A Preferred Stock with the Secretary of State of the State of Delaware in connection with the Closing.

Pursuant to the Registration Rights Agreement, the Purchaser has certain customary registration rights with respect to any shares of Series A Preferred Stock or the common stock of the Company issuable upon conversion of the Series A Preferred Stock, including rights with respect to the filing of a shelf registration statement, underwritten offering rights and piggy back rights.

Pursuant to the Registration Rights Agreement, the Purchaser has certain customary registration rights with respect to any shares of Series A Preferred Stock or the common stock of the

Company issuable upon conversion of the Series A Preferred Stock, including rights with respect to the filing of a shelf registration statement, underwritten offering rights and piggy back rights.

Dividend Provisions

40 unchanged sentences

See “ Note 12.

Series A Convertible Preferred Stock ” for a description of our Series A Preferred Stock, which is the only class of preferred stock outstanding.

Registration Statements

On October 21, 2022 we filed a resale registration statement on Form S-3 (File No.

333-267973) (the “2022 S-3”), on behalf of the Purchaser and pursuant to the Registration Rights Agreement, which became effective on November 1, 2022 and covers (i) the issued Series A Preferred Stock and (ii) the number of shares of the Company’s common stock issuable upon conversion of such Series A Preferred Stock, which amount includes and assumes that dividends on the Series A Preferred Stock are paid by increasing the Liquidation Preference of the Series A Preferred Stock for a period of sixteen dividend payment periods from the initial issuance date.

See “ Note 12.

Series A Convertible Preferred Stock ” for further details.

Mezzanine Equity —Series A Convertible Preferred Stock ” for a description of our Series A Preferred Stock, which is the only class of preferred stock outstanding.

Share repurchase program

1 unchanged sentence

In October 2023, the Board of Directors authorized an increase to the Share Repurchase Plan to allow the Company to repurchase up to an additional $ 10 million of shares.

The Share Repurchase Plan allows the Company to repurchase shares of its issued and outstanding Common Stock, from time to time in the open market or otherwise (including in negotiated transactions, open market transactions, through accelerated share repurchase, through indirect purchases of Common Stock such as by using derivatives or in other transactions) in each case in accordance with applicable securities laws, so long as the aggregate purchase price paid for such transactions does not exceed $ 25 million for all such purchases.

The Share Repurchase Plan does not have a specified expiration date.

Accordingly, unless terminated earlier by resolution of the Board, the Share Repurchase Plan will expire when the Company has repurchased all shares authorized for repurchase.

The Share Repurchase Plan expired in May 2024 when the Company had repurchased all shares authorized for repurchase.

In fiscal year 2024, the Company’s net stock repurchases are subject to a 1 percent excise tax under the Inflation Reduction Act.

The excise tax is included as a reduction to accumulated deficit in the consolidated statements of stockholders equity.

Total accrued excise tax of $ 0.1 million is included in total cost of shares repurchases, excluded from average cost per share and excluded from total cash paid during the year ended December 31, 2023 as amounts were unpaid at year end.

Total accrued excise tax of $ 0.2 million is included in total cost of shares repurchases, excluded from average cost per share and excluded from total cash paid during the years ended December 31, 2024 and 2023 as amounts were unpaid at year end.

During the year ended December 31, 2024, the Company repurchased and subsequently retired 3,208,705 shares of Common Stock, for a total of $ 11.0 million under the Share Repurchase Plan, inclusive of excise tax and other costs directly related to the repurchased shares.

As of December 31, 2023, approximately $ 10.8 million remained available for additional share repurchases.

As of December 31, 2024, no shares remained available for additional share repurchases.

The Company is not obligated to acquire any particular amount of Common Stock and may modify or suspend the repurchases at any time in the Company’s discretion.

As of December 31, 2024, the Share Repurchase Plan was complete and no further amounts are available for share repurchases.

Tax Benefit Preservation Plan and Preferred Stock Purchase Rights

On May 2, 2023, our Board of Directors authorized and declared a dividend of one preferred stock purchase right (a “Right”) for each outstanding share of Common Stock of the Company as of May 12, 2023 (the “Record Date”).

Effective June 5, 2024, after approval of the Board and the Companys’ stockholders, the Company entered into the 2024 Tax Benefit Preservation Plan with Broadridge Corporate Issuer Solutions, LLC, as Rights Agent (the “2024 Tax Benefit Preservation Plan”).

By adopting the 2024 Tax Benefit Preservation Plan, the Company is seeking to protect its ability to use its net operating loss carryforwards (“NOLs”) and other tax attributes to offset potential future income tax liabilities.

The Company’s ability to use such NOLs and other tax attributes would be substantially limited if the Company experiences an “ownership change,” as defined in Section 382 of the Internal Revenue Code.

The 2024 Tax Benefit Preservation Plan is intended to make it more difficult for the Company to undergo an ownership change by deterring any person from acquiring 4.9% or more of the outstanding shares of stock without the approval of the Board of Directors.

As part of the 2024 Tax Benefit Preservation Plan, the Board declared a dividend of one preferred stock purchase right (a “2024 Right”) for each outstanding share of Common Stock of the Company as of June 15, 2024.

27,030,605 Rights were issued to the holders of record of shares of Common Stock.

The description and terms of the Rights are set forth in a Tax Benefit Preservation Plan, dated as of May 2, 2023, as the same may be amended from time to time (the “Plan”), between the Company and Broadridge Corporate Issuer Solutions, LLC, as Rights Agent.

By adopting the Plan, the Board of Directors is seeking to protect the Company’s ability to use its net operating loss carryforwards (“NOLs”) and other tax attributes to offset potential future income tax liabilities.

Generally, an “ownership change” occurs if the percentage of the Company’s stock owned by one or more “five percent stockholders” increases by more than fifty percentage points over the lowest percentage of stock owned by such stockholders at any time during the prior three-year period or, if sooner, since the last “ownership change” experienced by the Company.

The Plan is intended to make it more difficult for the Company to undergo an ownership change by deterring any person from acquiring 4.9 % or more of the outstanding shares of stock without the approval of the Board of Directors.

The Board of Directors believes it is in the best interest of the Company and its stockholders to reduce the likelihood of an ownership change, which could harm the Company’s future operating results by effectively increasing the Company future tax liabilities.

The description and terms of the 2024 Rights are set forth in the 2024 Tax Benefit Preservation Plan.

The 2024 Rights trade with, and are inseparable from, the Common Stock, and the record holders of shares of Common Stock are the record holders of the 2024 Rights.

The Rights are evidenced only by certificates (or, in the case of uncertificated shares, by notations in the book-entry account system) that represent shares of Common Stock.

Rights will also be issued in respect of any shares of Common Stock that shall become outstanding after the Record Date (including upon conversion of any shares of Series A Preferred Stock of the Company) and, subject to certain exceptions specified in the Plan, prior to the earlier of the Distribution Date (as defined below) and the Expiration Date (as defined below).

The Rights are not exercisable until the Distribution Date.

After the Distribution Date, each Right will be exercisable to purchase from the Company one one-thousandth of a share of Series B Junior Participating Preferred Stock, par value $ 0.0001 per share, of the Company (the “Series B Preferred”), at a purchase price of $18.00 per one one-thousandth of a share of Series B Preferred (the “Purchase Price”), subject to adjustment as provided in the Plan.

The “Distribution Date” is the earlier of (i) the close of business on the tenth day after the public announcement that a person or group has become an Acquiring Person (as defined below) or that discloses information which reveals the existence of an Acquiring Person or such earlier date as a majority of the Board shall become aware of the existence of an Acquiring Person (the date described in this clause (i), the “Stock Acquisition Date”) and (ii) the close of business on the tenth business day (or such later date as the Board of Directors shall determine prior to such time as any person or group becomes an Acquiring Person) after the date that a tender or exchange offer by any person is commenced, the consummation of which would result in such person becoming an Acquiring Person.

A person or group becomes an “Acquiring Person” upon acquiring beneficial ownership of 4.9 % or more of the outstanding shares of Common Stock, except in certain situations specified in the Plan.

The Rights will expire on the earliest of (a) the close of business on May 1, 2024, (b) the time at which the Rights are redeemed or exchanged pursuant to the Plan, or (c) the time at which the Board of Directors determines that the Tax Benefits are utilized in all material respects or that an ownership change under Section 382 of the Code would not adversely impact in any material respect the time period in which the Company could use the Tax Benefits, or materially impair the amount of the Tax Benefits that could be used by the Company in any particular time period, for applicable tax purposes (such earliest date, the “Expiration Date”).

The 2024 Rights are not exercisable until the Distribution Date, as defined in the 2024 Tax Benefit Preservation Plan.

After the Distribution Date, each Right will be exercisable to purchase from the Company one one-thousandth of a share of Series B Junior Participating Preferred Stock, par value $ 0.0001 per share, of the Company (the “Series B Preferred”), at a purchase price of $15.25 per one one-thousandth of a share of Series B Preferred (the “Purchase Price”), subject to adjustment as provided in the 2024 Tax Benefit Preservation Plan.

Until a Right is exercised or exchanged, the holder thereof, as such, will have no rights as a stockholder of the Company by virtue of holding such Right, including, without limitation, the right to vote and to receive dividends.

1 unchanged sentence

No adjustments to the Purchase Price of less than 1 % are required to be made.

In connection with the adoption of the Plan, the Board of Directors approved a Certificate of Designations of the Series B Junior Participating Preferred Stock (the “Certificate of Designations”).

The Certificate of Designations was filed with the Secretary of State of the State of Delaware on May 2, 2023.

Each one one-thousandth of a share of Series B Preferred, if issued:

12 unchanged sentences

Unrealized translation loss on intercompany loans with foreign subsidiaries, net of taxes ( 6,477 ) ( 3,330 )

Unrealized gain on interest rate swaps 14,270 41,168

Unrealized gain on interest rate swaps, net of amounts reclassified into interest expense, net 9,033 14,270

Realized gain on interest rate swap sale, net of amounts reclassified into interest expense, net

Total accumulated other comprehensive income (loss) $ ( 21,990 ) $ 6,168

The Unrealized translation gain on intercompany loans with foreign subsidiaries as of December 31, 2023 is net of unrealized income tax expense of $ 1.6 million.

The Unrealized translation gains on intercompany loans with foreign subsidiaries as of December 31, 2024 and 2023 are net of unrealized income tax expense of $ 1.4 million and $ 1.6 million, respectively.

The income tax expense (benefit) allocated to each component of other comprehensive income (loss) for all other periods and components was not material.

Stock Compensation Plans

The Company maintains two stock-based compensation plans, the 2010 Stock Option Plan (the “2010 Plan”) and the 2014 Stock Option Plan (the “2014 Plan”), which are described below.

At December 31, 2023, there were 27,939 options outstanding under the 2010 Plan.

Following the effectiveness of the Company’s 2014 Plan in November 2014, no further awards have been made under the 2010 Plan, although each option previously granted under the 2010 Plan will remain outstanding subject to its terms.

Any such shares of common stock that are subject to awards under the 2010 Plan which are forfeited or lapse unexercised and would otherwise have been returned to the share reserve under the 2010 Plan instead will be available for issuance under the 2014 Plan.

In November 2014, the Company adopted the 2014 Plan, providing for the granting of incentive stock options, as defined by the Internal Revenue Code, to employees and for the grant of non-statutory stock options, stock appreciation rights, restricted stock, restricted stock units, performance units and performance shares to employees, directors and consultants.

The 2014 Plan also provides for the automatic grant of option awards to our non-employee directors.

As of December 31, 2023, there were 121,975 options outstanding under the 2014 Plan, and 737,581 shares of common stock reserved for issuance under the 2014 Plan.

The number of shares available for issuance under the 2014 Plan will be increased annually through 2024 in an amount equal to the least of (i) 4 % of the outstanding Shares on the last day of the immediately preceding Fiscal Year or (ii) such number of Shares determined by the Board.

At December 31, 2023, there were 1,758,847 restricted stock units and 100,000 performance based restricted stock units outstanding under the 2014 Plan.

Under both the 2010 Plan and 2014 Plan, options granted to date generally vest over a three or four year period, with a maximum term of ten years .

Shares issued upon any stock option exercise and restricted under the 2010 Plan or 2014 Plan will be issued from the Company's authorized but unissued shares.

Stock-Based Compensation Plans

The Company’s stock-based compensation generally includes awards of restricted stock units (“RSUs”) and performance-based restricted stock units (“PRSUs”).

Key employees, officers and directors of the Company and its consultants or advisors are eligible to receive awards.

On June 5, 2024, the Company’s stockholders approved the Upland Software, Inc.

2024 Omnibus Incentive Plan.

No further awards will be made under the Upland Software, Inc.

2014 Equity Incentive Plan or the Amended and Restated Upland Software, Inc.

2010 Stock Option Plan (collectively, the “Plans”).

At December 31, 2024, there were 103,561 options outstanding under the Company’s Plans, 2,177,132 restricted stock units and 100,000 performance based restricted stock units outstanding under the Plans.

At December 31, 2024, there were 2,725,017 shares of common stock reserved for issuance under the Plans.

Share-based Compensation

6 unchanged sentences

General and administrative 10,898 17,400 32,646

17,400 32,646 42,743

Total $ 15,270 $ 22,874 $ 41,602

(1) For the year ended December 31, 2021, a former executive resigned from his positions that resulted in stock-based compensation of $ 6.3 million related to the acceleration and deemed modification of the unvested portion of grants held at the time of transition.

In accordance with ASC 718, Compensation—Stock Compensation , the fair value of these awards were modified and all related expense accelerated on the date of modification as a result of the reduction in required service.

Our income tax benefits recognized from stock-based compensation arrangements in each of the periods presented were immaterial due to cumulative losses and valuation allowances.

Restricted Stock Units (“RSU”)

During the year ended December 31, 2023 the Company granted restricted stock units under its 2014 Stock Incentive Plan, in lieu of restricted stock awards, primarily for stock plan administrative purposes.

Performance-Based Restricted Stock Units (“PRSU”)

Restricted stock units primarily vest over a period of 1 to three years upon the satisfaction of a service-based condition with quarterly vesting.

The total fair value of the RSUs vested during the years ended December 31, 2024, 2023 and 2022 was approximately $ 4.3 million, $ 5.0 million and $ 13.9 million, respectively.

Performance-Based Restricted Stock Units

In 2024, 2023 and 2022, fifty percent of the awards granted to our Chief Executive Officer were PRSUs.

The 2023 and 2022 PRSU agreements provide that the quantity of units subject to vesting may range from 0 % to 300 % of the units granted per the table below based on the Company's absolute total shareholder return (“TSR”) at the end of the thirty-six and eighteen month performance periods, respectively.

At the end of the performance period, the 2022 PRSU resulted in no units granted.

The PRSU agreements provide that the quantity of units subject to vesting may range from 0 % to 300 % of the units granted based on the Company's absolute total shareholder return (“TSR”) at the end of thirty-six month performance periods for the 2024 and 2023 PRSUs and an 18 month performance period for the 2022 PRSUs.

In December 2024, 750,000 of 2024 PRSUs vested when the TSR met the performance criteria.

The 2023 PRSU has not vested as of year ended December 31, 2024.

The 2022 PRSU resulted in no units granted at the end of their performance period on June 30, 2023.

The total fair value of PRSUs vested during the years ended December 31, 2024, 2023 and 2022 was $ 3.5 million, nil , and nil , respectively.

Significant assumptions used in the Monte Carlo simulation model for the PRSUs granted during the year ended December 31, 2024 and year ended December 31, 2023 are as follows:

December 31, 2024 December 31, 2023

Expected volatility 74.6 % - 62.1 %

Risk-free interest rate 4.4 % - 4.0 %

Remaining performance period (in years) 2.73 - 3.08

Dividend yield — —

The risk-free interest rate assumption is based upon observed interest rates for constant maturity U.S.

Treasury securities as of the grant date.

Expected volatility is based on the historical volatility of the Company’s common stock over the estimated expected life.

The Company does not pay a dividend, therefore, the dividend yield is assumed to be zero.

The following table summarizes PRSU and RSU activity during the year ended December 31, 2024 :

4 unchanged sentences

Forfeited ( 205,813 ) 8.70

( 404,727 ) 22.60

Unvested restricted units outstanding as of December 31, 2024 2,277,132 $ 5.36

(1) Includes forfeited awards related to the 2022 PRSUs.

At June 30, 2023, or the end of the performance period for the 2022 PRSUs, none of the awards vested.

The total fair value of the RSUs vested during the years ended December 31, 2023, 2022 and 2021 was approximately $ 5.0 million, $ 13.9 million and $ 28.2 million, respectively.

As of December 31, 2023, $ 16.0 million of unrecognized compensation cost related to unvested restricted stock units (including performance based awards) is expected to be recognized over a weighted-average period of 1.77 years.

The PRSU and RSU activity table above includes PRSU units granted that are based on a 100 % target payout.

The total fair value of PRSUs vested during the years ended December 31, 2023, 2022 and 2021 was nil , nil and $ 5.6 million, respectively.

Significant assumptions used in the Monte Carlo simulation model for the PRSUs granted during the year ended December 31, 2023 and year ended December 31, 2022 are as follows:

December 31, 2023 December 31, 2022

Expected volatility 55.5 % 49.5 %

Risk-free interest rate 4.4 % 0.7 %

Remaining performance period (in years) 2.86 1.46

Dividend yield — —

As of December 31, 2024, $ 8.6 million of unrecognized compensation cost related to unvested restricted stock units (including performance based awards) is expected to be recognized over a weighted-average period of 1.72 years.

Stock Option Activity

Under the Plans, options granted to date generally vest over a three or four year period, with a maximum term of ten years .

Stock option activity during the year ended December 31, 2024 is as follows:

10 unchanged sentences

Options vested and exercisable at December 31, 2024 103,561 $ 10.77 1.49 $ —

The aggregate intrinsic value of options exercised at December 31, 2023, 2022, and 2021, was approximately nil , $ 0.6 million, and $ 1.1 million, respectively.

The aggregate intrinsic value of options exercised at December 31, 2024, 2023, and 2022, was approximately nil , nil , and $ 0.6 million, respectively.

All of the Company’s outstanding stock options were fully vested as of December 31, 2019.

45 unchanged sentences

The Company's control is evidenced by its involvement in the integration of the good or service on its platform before it is transferred to its customers, and is further supported by the Company being primarily responsible to its customers and having a level of discretion in establishing pricing.

While none of the factors individually are considered presumptive or determinative, in reaching conclusions on gross versus net revenue recognition, the Company places the most weight on the analysis of whether or not it is the primary obligor in the arrangement.

While none of the factors individually are considered presumptive or

determinative, in reaching conclusions on gross versus net revenue recognition, the Company places the most weight on the analysis of whether or not it is the primary obligor in the arrangement.

Generally, the Company reports revenue from vendor reseller agreements on a gross basis, meaning the amounts billed to customers are recorded as revenue, and expenses incurred are recorded as cost of revenue.

76 unchanged sentences

Our Chief Executive Officer is considered to be our CODM.

Our CODM manages the business as a multi-product business that utilizes its model to deliver software products to customers regardless of their geography or IT environment.

Our CODM manages the business as a multi-product cloud-based software application business that utilizes a singular operating model to deliver a consistently high level of operating performance to customers regardless of their geography or IT environment.

Operating results are reviewed by the CODM primarily at the consolidated entity level for purposes of making resource allocation decisions and for evaluating financial performance.

Accordingly, we considered ourselves to be in a single operating and reporting segment structure.

The key measure of profit or loss utilized by the CODM to assess performance of and allocate resources within the Company’s single operating segment is net loss.

This measure is presented on the consolidated statements of operations.

Significant segment expenses included in net loss are cost of revenue, sales and marketing expenses, research and development expenses, general and administrative expenses, depreciation and amortization, interest expense, net and other income (expense), which

are presented on the consolidated statements of operations.

The measure of segment assets is reported on the consolidated balance sheets as total assets.

Accordingly, we consider ourselves to be in a single operating and reporting segment structure.

See “ Note 14 Revenue Recognition—Disaggregated Revenue ” for a detail of revenue by geography.

6 unchanged sentences

Total identifiable long-lived assets $ 1,518 $ 1,932

Subsequent Events

The Company completed the disposition of certain assets in the first quarter of 2025 for $ 9.5 million consisting of cash and other consideration.

The Company estimates it will record a loss on the transactions which will be recognized as Loss on divestitures in the Company’s condensed consolidated statements of operations for the three months ended March 31, 2025.

The Company used the cash proceeds to further paydown its outstanding Term Loans.

Changes in and Disagreements with Accountants on Accounting and Financial Disclosure

Compared sentence by sentence after normalising whitespace, quotation marks, case and digits, so re-formatting and restated figures do not read as changed language. Wording changes appear as one removal and one addition. The current filing and the prior one are authoritative.

What changed 10-K

Item 8. Financial Statements and Supplementary Data