UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2019 OR ¨ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission File Number 001-36720 Upland Software, Inc. (Exact name of registrant as specified in its charter) Delaware 27-2992077 (I.R.S. Employer Identification Number) (State or other jurisdiction of inc ...

Upland Software, Inc. (NASDAQ:UPLD) Q4 2019 Earnings Conference Call February 27, 2020 5:00 PM ET Company Participants Jack McDonald – Chairman and Chief Executive Officer Mike Hill – Chief Financial Officer Tim Mattox – President and Chief Operating Officer Conference Call Participants Kamil Mielczarek – William Blair Brent Thill – Jefferies Jeff Van Rhee – Craig-Hallum Richard Baldry – Roth Capital Terry Tillman – SunTrust Robinson Alex Sklar – Raymond James Operator Ladies and gentlemen, thank you for st ...

Upland Overview January 2020 Safe Harbor Statement This presentation includes "forward-looking statements," which are subject to substantial risks, uncertainties and assumptions, subject to the safe harbor provisions of the Private Securities Litigation Reform Act of 1995. 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 "believ ...

Upland Overview December 2019 Safe Harbor Statement This presentation includes "forward-looking statements," which are subject to substantial risks, uncertainties and assumptions, subject to the safe harbor provisions of the Private Securities Litigation Reform Act of 1995. 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 "belie ...

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2019 OR ¨ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-36720 UPLAND SOFTWARE, INC. (Exact name of registrant as specified in its charter) State of Delaware 27-2992077 (Stat ...

Upland Software, Inc. (NASDAQ:UPLD) Q3 2019 Results Conference Call November 7, 2019 5:00 PM ET Company Participants Jack McDonald - Chairman and Chief Executive Officer Mike Hill - Chief Financial Officer Tim Mattox - President and Chief Operating Officer Conference Call Participants Brad Zelnick - Credit Suisse Bhavan Suri - William Blair Luv Sodha - Jefferies Brian Peterson - Raymond James Eric Lemus - SunTrust Operator Ladies and gentlemen thank you for standing by and welcome to the Upland Software Thi ...

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Part I. FINANCIAL INFORMATION [Item 1. Financial Statements (unaudited)](index=4&type=section&id=Item%201.%20Financial%20Statements%20(unaudited)) Upland Software, Inc.'s unaudited condensed consolidated financial statements for the period ended June 30, 2019, reflect significant asset and revenue growth, primarily from acquisitions, alongside increased operating losses and debt [Condensed Consolidated Balance Sheets](index=4&type=section&id=Condensed%20Consolidated%20Balance%20Sheets) As of June 30, 2019, total assets increased to **$657.6 million**, driven by cash from a stock offering and acquisition-related goodwill and intangibles, while total liabilities rose to **$424.6 million** due to higher notes payable Condensed Consolidated Balance Sheets (in thousands of USD) | | June 30, 2019 | December 31, 2018 | | :--- | :--- | :--- | | **Total current assets** | $157,014 | $67,288 | | **Goodwill** | $273,363 | $225,322 | | **Intangible assets, net** | $207,232 | $179,572 | | **Total assets** | **$657,580** | **$483,198** | | **Total current liabilities** | $107,472 | $107,649 | | **Notes payable, less current maturities** | $305,335 | $273,713 | | **Total liabilities** | **$424,608** | **$395,891** | | **Total stockholders' equity** | **$232,972** | **$87,307** | [Condensed Consolidated Statements of Operations](index=6&type=section&id=Condensed%20Consolidated%20Statements%20of%20Operations) Q2 2019 total revenue increased **47%** to **$53.0 million**, but a significant rise in operating expenses, including **$9.3 million** in acquisition-related costs, led to a net loss of **$5.4 million** Condensed Consolidated Statements of Operations (in thousands of USD, except per share data) | | Three Months Ended June 30, 2019 | Three Months Ended June 30, 2018 | | :--- | :--- | :--- | | **Total revenue** | $53,013 | $35,946 | | **Gross profit** | $36,430 | $25,097 | | **Loss from operations** | $(5,532) | $(691) | | **Net loss** | **$(5,369)** | **$(5,230)** | | **Net loss per common share, basic and diluted** | $(0.24) | $(0.26) | [Condensed Consolidated Statements of Comprehensive Loss](index=7&type=section&id=Condensed%20Consolidated%20Statements%20of%20Comprehensive%20Loss) The company reported a comprehensive loss of **$7.1 million** for Q2 2019, including a **$5.4 million** net loss and a **$1.8 million** foreign currency translation adjustment loss Condensed Consolidated Statements of Comprehensive Loss (in thousands of USD) | | Three Months Ended June 30, 2019 | Three Months Ended June 30, 2018 | | :--- | :--- | :--- | | **Net loss** | $(5,369) | $(5,230) | | **Foreign currency translation adjustment** | $(1,757) | $(2,227) | | **Comprehensive loss** | **$(7,126)** | **$(7,457)** | [Condensed Consolidated Statements of Stockholders' Equity](index=8&type=section&id=Condensed%20Consolidated%20Statements%20of%20Stockholders'%20Equity) Total stockholders' equity significantly increased to **$233.0 million** by June 30, 2019, primarily due to a **$151.2 million** increase in additional paid-in capital from a common stock issuance - A public offering of 3,795,000 shares of common stock resulted in a **$151.2 million** increase in additional paid-in capital during the six months ended June 30, 2019[23](index=23&type=chunk) [Condensed Consolidated Statements of Cash Flows](index=10&type=section&id=Condensed%20Consolidated%20Statements%20of%20Cash%20Flows) For the first six months of 2019, operating activities provided **$5.4 million** in cash, investing activities used **$83.2 million** for acquisitions, and financing activities provided **$168.6 million**, leading to a **$91.6 million** increase in cash and equivalents Condensed Consolidated Statements of Cash Flows (in thousands of USD) | | Six Months Ended June 30, 2019 | Six Months Ended June 30, 2018 | | :--- | :--- | :--- | | **Net cash provided by operating activities** | $5,396 | $3,740 | | **Net cash used in investing activities** | $(83,188) | $(45,877) | | **Net cash provided by financing activities** | $168,617 | $39,220 | | **Change in cash and cash equivalents** | $91,623 | $(3,289) | | **Cash and cash equivalents, end of period** | **$108,361** | **$19,037** | [Notes to Condensed Consolidated Financial Statements](index=11&type=section&id=Notes%20to%20Condensed%20Consolidated%20Financial%20Statements) The notes detail accounting policies and financial items, including two 2019 acquisitions contributing **$3.8 million** in revenue, the adoption of ASU 2016-02 recognizing **$6.3 million** in right-of-use assets, subsequent debt refinancing, and **$161.1 million** in remaining performance obligations - Completed the acquisitions of Postup Holdings and Kapost in Q2 2019, contributing approximately **$2.4 million** and **$1.4 million** in revenue, respectively, since their acquisition dates[45](index=45&type=chunk) - Adopted the new lease standard ASU 2016-02 on January 1, 2019, recognizing **$6.3 million** in right-of-use assets and corresponding lease liabilities[41](index=41&type=chunk)[42](index=42&type=chunk) - As of June 30, 2019, the company had approximately **$161.1 million** of revenue expected from remaining performance obligations, with **71%** anticipated in the next 12 months[116](index=116&type=chunk) - Subsequent to the quarter end, on August 6, 2019, the company entered into a new **$350 million** senior secured term loan B facility and a new **$60 million** revolving credit facility, replacing its existing credit facility[121](index=121&type=chunk) [Management's Discussion and Analysis of Financial Condition and Results of Operations](index=31&type=section&id=Item%202.%20Management's%20Discussion%20and%20Analysis%20of%20Financial%20Condition%20and%20Results%20of%20Operations) Management attributes Q2 2019's **47%** revenue growth primarily to acquisitions, with Adjusted EBITDA rising to **$19.1 million**, while acquisition-related expenses increased **195%**, and liquidity improved significantly with cash reaching **$108.4 million** after a **$151.1 million** stock offering [Overview](index=32&type=section&id=Overview) Upland provides cloud-based enterprise work management software, driving growth primarily through **twenty-two acquisitions** from 2012 to 2019, increasing revenue from **$22.8 million** to **$149.9 million** and expanding international revenue share - The company's growth strategy involves acquiring complementary technologies and businesses to expand product families, customer base, and market access[133](index=133&type=chunk) - Revenue grew from **$22.8 million** in 2012 to **$149.9 million** in 2018, representing an approximate **558%** growth rate[132](index=132&type=chunk) [Key Metrics](index=33&type=section&id=Key%20Metrics) Adjusted EBITDA, a key non-GAAP metric, increased to **$19.1 million** for Q2 2019 and **$36.9 million** for the six months ended June 30, 2019, reflecting improved operational performance Reconciliation of Net Loss to Adjusted EBITDA (in thousands of USD) | | Three Months Ended June 30, 2019 | Three Months Ended June 30, 2018 | | :--- | :--- | :--- | | **Net loss** | $(5,369) | $(5,230) | | **Adjustments** | $24,452 | $17,775 | | **Adjusted EBITDA** | **$19,083** | **$12,545** | [Results of Operations](index=35&type=section&id=Results%20of%20Operations) Q2 2019 total revenue increased **47%** to **$53.0 million**, driven by acquisitions, while operating expenses, particularly acquisition-related costs, rose **195%** to **$9.3 million**, reflecting the company's growth strategy - Q2 2019 total revenue increased by **$17.1 million** (**47%**) year-over-year, with **$15.2 million** attributed to acquisitions not fully in the comparative period[146](index=146&type=chunk) - Acquisition-related expenses for Q2 2019 were **$9.3 million**, a **195%** increase from **$3.1 million** in Q2 2018, reflecting recent transaction costs[178](index=178&type=chunk)[179](index=179&type=chunk) - A tax benefit of **$6.1 million** was recorded in Q2 2019, compared to a **$0.9 million** provision in Q2 2018, primarily due to the release of a valuation allowance from domestic entity acquisitions with deferred tax liabilities[187](index=187&type=chunk) [Liquidity and Capital Resources](index=47&type=section&id=Liquidity%20and%20Capital%20Resources) The company's liquidity significantly improved in H1 2019, with cash and cash equivalents rising to **$108.4 million** due to **$151.1 million** net proceeds from a May 2019 stock offering, and subsequent debt refinancing with a new **$350 million** term loan - Cash and cash equivalents increased to **$108.4 million** as of June 30, 2019, largely due to a public stock offering[191](index=191&type=chunk) - In May 2019, the company completed a public offering of 3,795,000 shares, raising net proceeds of **$151.1 million**[197](index=197&type=chunk) - On August 6, 2019, the company replaced its existing credit facility with a new **$350 million** term loan and a **$60 million** revolving credit facility[195](index=195&type=chunk) [Item 3. Quantitative and Qualitative Disclosures About Market Risk](index=50&type=section&id=Item%203.%20Quantitative%20and%20Qualitative%20Disclosures%20About%20Market%20Risk) The company identifies interest rate risk on variable-rate debt, foreign currency exchange risk from international operations, and inflation as primary market risks, noting a **$0.3 million** impact from a 100 basis point interest rate change and a **$3.0 million** revenue impact from a 10% foreign exchange rate change - A hypothetical 100 basis point change in interest rates would result in a maximum potential change to annual interest expense of **$0.3 million** based on debt levels at June 30, 2019[213](index=213&type=chunk) - A hypothetical **10%** change in foreign currency exchange rates would have resulted in a change in revenue of **$3.0 million** for the six months ended June 30, 2019[214](index=214&type=chunk) [Item 4. Controls and Procedures](index=51&type=section&id=Item%204.%20Controls%20and%20Procedures) Management, including the CEO and CFO, concluded that the company's disclosure controls and procedures were effective as of June 30, 2019 - Management, including the CEO and CFO, concluded that the company's disclosure controls and procedures were effective as of June 30, 2019[219](index=219&type=chunk) Part II. OTHER INFORMATION [Item 1A. Risk Factors](index=52&type=section&id=Item%201A.%20Risk%20Factors) There have been no material changes to the risk factors disclosed in the company's 2018 Annual Report on Form 10-K, referring stakeholders to that document for a comprehensive overview - There have been no material changes during 2019 to the risk factors included in the company's 2018 Annual Report on Form 10-K[222](index=222&type=chunk) [Item 6. Exhibits](index=52&type=section&id=Item%206.%20Exhibits) This section indexes all exhibits filed with the Form 10-Q, including CEO and CFO certifications required by Sarbanes-Oxley Act and XBRL data files - The Exhibit Index lists certifications from the CEO and CFO pursuant to Sarbanes-Oxley Act Sections 302 and 906, along with XBRL instance and taxonomy documents[226](index=226&type=chunk)

Upland Software, Inc. (NASDAQ:UPLD) Q2 2019 Results Conference Call August 7, 2019 5:00 PM ET Company Participants Jack McDonald – Chairman and Chief Executive Officer Mike Hill – Chief Financial Officer Tim Mattox – President and Chief Operating Officer Conference Call Participants Bhavan Suri – William Blair John DiFucci – Jefferies Richard Davis – Canaccord Genuity Jeff Van Rhee – Craig-Hallum Joshua Reilly – Needham Brian Peterson – Raymond James Richard Baldry – Roth Capital Eric Lemus – SunTrust Robin ...

Company Overview - Upland Software is an Enterprise Work Management (EWM) cloud provider with headquarters in Austin, TX[10] - The company has over 9,000 customers and more than 1,000,000 global users[10] - Upland targets a $25 billion Total Addressable Market (TAM) with an average ARR (Annual Recurring Revenue) of over $100,000 per major account[10] - The company boasts a high recurring revenue model, with over 90% recurring revenue[10] - Upland has a high net dollar retention rate (DRR) of 98%[10, 43] Financial Performance - The company's annual revenue run-rate is over $205 million, based on the annualized run-rate of total revenue for the quarter ended March 31, 2019, plus pro-forma total revenue from the Post-Up acquisition[10] - Upland experienced 62% year-over-year recurring revenue growth for the quarter ended March 31, 2019[10, 43] - The company's Adjusted EBITDA margin is 37% of revenue, based on the quarter ending March 31, 2019[10, 43] - Upland has a revenue growth CAGR (Compound Annual Growth Rate) of 40% from 2016 to 2019 (estimated)[42] M&A Strategy - Upland aims to add $25-$50 million in revenue run-rate per year through acquisitions[28] - The company targets businesses with $5-25 million in revenue, a sticky customer base with 90%+ Net Dollar Retention Rate (NDRR), and 70%+ gross margins[28]