#1U Investor Presentation June 2021 1#2This 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 "believe," "expect," "anticipate," "intend," "plan," "assume," "assumption," "forecast," "estimate," "theoretical," "seek," "will," "may" or similar expressions. Actual results may differ materially from those indicated by such forward-looking statements as a result of various important factors, including: our financial performance and our ability to achieve, sustain or increase profitability or predict financial results; our ability to generate adequate cash flows from our business; our ability to attract and retain customers; our ability to deliver high-quality customer service; lack of demand growth for our applications; our ability to effectively manage our growth; our ability to continue to consummate and integrate acquisitions and mergers; our ability to manage and predict costs related to our acquisition program; our ability to maintain our senior management and key personnel; our ability to maintain and expand our direct sales organization; our ability to obtain financing in the future on acceptable terms or at all; the performance of our resellers; our ability to adapt to changing market conditions and competition; our ability to successfully enter new markets and manage our international expansion; fluctuations in currency exchange rates; the operation and reliability of our third-party data centers and other service providers; and factors that could affect our business and financial results identified in Upland's filings with the Securities and Exchange Commission (the "SEC"), including Upland's most recent 10-K, filed with the SEC on February 25, 2021. Additional information will also be set forth in Upland's future quarterly reports on Form 10-Q, annual reports on Form 10-K and other filings that Upland makes with the SEC. The forward-looking statements herein represent Upland's views as of the date of this presentation and these views could change. However, while Upland may elect to update these forward-looking statements at some point in the future, Upland specifically disclaims any obligation to do so. These forward-looking statements should not be relied upon as representing the views of Upland as of any date subsequent to the date of this presentation. Refer to our reconciliations of Adjusted EBITDA to Net Income in our Form 10-Q filings, Form 10-K filing, and earnings press releases. U Safe Harbor Statement 2#3Jack McDonald Founder, Chairman, and CEO • Serial entrepreneur, led two NASDAQ IPOS (UPLD + • • • PRFT), creating $3B+ in enterprise value Leading consolidator of tech businesses, completing 50 acquisitions in 20 years Ernst & Young Entrepreneur of the Year Award winner Prior to UPLD, led PRFT (1999-2010) from startup to $250MM revenue global IT consulting leader U Presenters Mike Hill CFO • . · CFO of PRFT (2004-2007) from $30MM to over $200MM annual revenue run-rate Executed as CFO 38+ successful technology acquisitions across three companies Started career at Ernst & Young LLP (1991 - 1999) 3#4U 1 . 1 We help global businesses accelerate digital transformation with a cloud software library that delivers choice, flexibility, and value . . 1 . 4#5Upland: Built to Deliver Decades of Value Powerful software library Extensive and growing library of 28 cloud software products that can operate at enterprise scale and deliver quick time to value Proven operating platform Scalable operating platform serving 1,700+ enterprise customers with global product innovation, service, support, and distribution Equity Compounder Sustainable, self-funded grower of high margin recurring revenue and free cash flow with attractive organic and M&A capital allocation opportunities OXOX X x o o O x x о x <-- сл 5#6Upland Product Library Name a challenge. We've got a product to solve it. All products Business Operations Contact Center HR & Legal Information Technology Marketing Project Management Sales U AccuRoute Secure document capture and delivery with optical character recognition. ✔ Adestra Enterprise marketing and email automation software that inspires engagement. Altify Account planning software to grow revenue and win the deals that matter. BlueVenn Customer data platform with omnichannel orchestration to unify data, decisions, and channels. ✔ Cimpl Telecom expense and inventory management to streamline costs. and processes. ComSci IT financial management software with managed service expertise. InGenius CRM phone integration that ignites agent efficiency. Intelligent Capture Document capture software with cloud-based routing and fax. Eclipse PPM Project portfolio management software that's quick to learn and easy to use. InterFAX Secure cloud-based fax service with enterprise-grade API. FileBound A document management system for reliable, user-friendly content workflow. ✔ Kapost Content operations software to create digital assets that drive conversions. Localytics Mobile app marketing software and analytics to understand user behavior. Mobile Messaging Text messaging software with feature-rich SMS, MMS, and mobile wallet. ✔ PostUp Enterprise email marketing for publishers. ✔ PowerSteering Project portfolio management software for complex organizations. PSA Professional services automation to drive planning, execution, and profit. Qvidian RFP response and proposal management software to win new business faster. Rant & Rave Customer engagement software for voice-of-customer insights and feedback. RightAnswers Knowledge management software to improve IT, customer support, and beyond. RO Innovation Customer reference software to strengthen relationships and close. deals faster. Ultriva Supply chain management to eliminate blind spots and optimize efficiency. uplandsoftware.com/products CO 6#7U CASE STUDIES Solving last mile business problems for global enterprises We deliver the plug-in processes, reporting, and job specific workflows that major cloud platforms and homegrown systems don't provide. Major European telco provider Sales account planning Hundreds of sales representatives map their account plans using Altify running on top of Salesforce. Leading financial services provider Complex proposal development Bid teams use Qvidian to assemble and track compliance for large sales proposals. Major insurance provider Fast answers for call center agents Thousands of agents use RightAnswers knowledge management product to respond to customer questions about complex insurance policies. 000000000000000 00000000000000000 0000000000000000000000000000 0000000000000000000000000 000000000 10000200020 00000000000000 00000000 00000000#8Customers love our products Source: Direct Quotes from our Q2 2021 Customer Survey AccuRoute provides an easy way for our users to generate a quality document scan and bill our clients all in one workflow. It also integrates seamlessly with many of our firm's core applications. Upland cares about their customers and provides high quality support when you need it. The InGenius Integration with Salesforce helps to streamline call center agents' workflow. Great Company and Great Product! Administrator National Law Firm Manager Health Services Provider Qvidian has great features and functionality that fits our needs. They're always innovating and improving the capabilities. Support and response when you have questions or need assistance is always A+. PowerSteering is an excellent all-around portfolio management system, which makes it pretty easy to sell internally to people who will be using it. Flexible and allows for a lot of back-end configuration in house which Upland have always been very supportive of. Senior Manager Global Tech Company Program Manager Hospital System 8 00#9+ U Why global businesses ++ choose us +++ +++++ ++++++ Choice Comprehensive catalog of proven products that deliver critical "last mile" capabilities at enterprise scale Flexibility Configurable to fit customer processes and work with existing infrastructure Value Global innovation, service, and support from a stable, long term partner ++++++ +++++++ +++++++ 6#10UplandOne is our proven operating platform Scalable with high customer satisfaction and high margins 100% Customer Success Culture Driven by customer priorities and feedback Enterprise-Grade Delivery AWS, global customer support and services Global Product Innovation Focused innovation from worldwide talent Account-Based Sales Distribution Bringing powerful cloud tools to market at scale 94% Net Dollar Retention Rate (1) Satisfied Customers 32% Adjusted EBITDA margin(2) Higher Margins Source: Company information and management (1) As disclosed in our Form 10-K as of December 31, 2020. (2) Based on the mid-point of our guidance range for the year ended December 31, 2021, as disclosed in our May 5, 2021 Form 8-K. 10#11Digital Transformation Digital transformation is just getting started. Business & professional services 17.0% Healthcare system 24.3% Media 25.0 % Consumer packaged goods 28.5% Financial services 29.7% Source: McKinsey Global Institute Automotive & telecom assembly Retail Travel 31.0% 24.1% Average completion across industry 46.0% 51.0% 11#12We focus on essential categories CXM $8.5B Knowledge Management $1.9B O 2021 Upland Software, Inc. Project & Financial Management $4.7B ~$25B TAM Sources: Gartner Enterprise Software Forecast Q2 2020 Gartner Market Share All Software Markets Worldwide 2019 https://www.openpr.com/news/2000791/knowledge-management- software-market-share-size-2020-global http://www.marketsandmarkets.com/Market-Reports/customer- experience-management-cem-market-543.html https://aragonresearch.com/sales-engagement/ Sales Enablement $3B Document Automation $6.5B 12#13We acquire proven products Expectations Hype M Uncertainty U Value The New Thing Time | 28 acquisitions to date Robust and growing pipeline of VC portfolio targets that have survived hype and uncertainty | Immediately accretive Disciplined pricing and proven integration playbook drive high acquisition IRRS and AEBITDA multiple arbitrage Proven cloud tools for global businesses Solve last mile problems at enterprise scale with quick time to value Upland provides the momentum We provide the balance sheet, global support, and sales distribution to get these products to market at scale 13#14We have 1,700+ Enterprise Customers Financial Services Manufacturing, Industrial Goldman Sachs Fidelity JPMorgan Chase PAYCHEX WELLS FARGO Abbott EMERSON. IR Ingersoll Rand PPG INVESTMENTS Inspiring Progress" Government, Nonprofit, Education American Red Cross HUMAN RIGHTS The Nature Conservancy CAMPAIGN NAV Technology A יווייוויי CISCO Adobe DOLL Telecom & Media 95 KATES Hewlett Packard Enterprise Thermo Fisher SCIENTIFIC $150K ARR Average annual spend per enterprise customer CenturyLink hp RICOH xerox R REALTOR NATIONAL ASSOCIATION of REALTORS® Corporate Services ADP Healthcare SAP Cigna. MCKESSON MERCK Pfizer UnitedHealthcare Medicare Solutions (v) Consumer, Retail COMCAST DISNEY HBO NBC UNIVERSAL VIACOM Coca-Cola MARY KAY MillerCoors Nestle PEPSICO A MOLSON C COMPANY 1.X Average products per account means large expansion and cross sell opportunity 10,000+ Total customer base 14#15Building a complete selling organization Supported by refreshed brand, digital focus, centralized marketing Industry focused Top 175 customers in 8 target industries Buying Center focused Cross-sell outside global account base and... Top target accounts in key functions across front and back office NEW NEW NEW Global Account Managers Inside Sales Development Team Solutions Consulting Team Renewals Team Product Sales Account Team Lead Qualification Product Experts Executives Commercial Accounts Cross- trained Coming soon 15#16Investment Highlights Powering Digital Transformation $25B+ TAM, delivering choice, flexibility, and value to global enterprises Powerful Library of Cloud Tools 28+ cloud products that solve last mile problems at enterprise scale and deliver quick time to value UplandOne Operating Platform Global innovation, service, support and distribution delivers high customer satisfaction and margins Large Enterprise Customer Base 1,700+ enterprise accounts and 10,000+ total customers represent a large expansion and cross-sell opportunity Equity Compounder Self-funded 15%+ target total revenue growth (organic plus acquisition growth) with strong FCF conversion and attractive capital allocation opportunities Self-Funded Growth Capital and tax efficient high FCF model is self-funding with no dependence on equity capital markets Sustainable Advantage Cloud/DT tailwinds, diversified recurring revenue, blue chip customer base/switching costs, low-cost provider, pole position for small cloud acquisitions 16#17U Financial Overview 17#18Financial Highlights 41% Revenue growth CAGR '16A-'20A(1) >95% Recurring Revenue(2) 94% Net Dollar Retention Rate(3) 32% Adjusted EBITDA margin (4) Target 40% at scale Strong free cash flow conversion Low CAPEX, tax efficient Disciplined use of leverage Target Leverage 3.0 - 4.0x Source: (1) Calculated based on annual revenue for the years ended December 31, 2016 and 2020. (2) Recurring revenue is also known as subscription and support revenue; based on subscription and support revenue as disclosed in our Form 10-K for the year ended December 31, 2020. (3) As disclosed in our Form 10-K as of December 31, 2020. (4) Based on the mid-point of our guidance range for the year ended December 31, 2021, as disclosed in our May 5, 2021 Form 8-K. See appendix for definition and reconciliation of Adjusted EBITDA. 18#19Annual Revenue ($ in millions) Prof. Serv. & License Recurring (2) $291.8 Annual Revenue Growth Trend Growth Drivers 4 Year CAGR: 41%(3) Accretive acquisitions 94% net dollar retention rate (1) Installed base expansion $98.0 $74.8 $149.9 $136.6 Price uplift, platinum support $85.5 $65.6 Efficient new logo acquisition 2016 $222.6 $203.9 $277.5 2017 2018 2019 2020 Actuals Source: Company information and management (1) As disclosed in our Form 10-K as of December 31, 2020. (2) Recurring revenue is also known as subscription and support revenue. (3) Calculated based on annual revenue for the years ended December 31, 2016 and 2020. 19#20Annual Adjusted EBITDA ($ in millions) $12.6 2016 $30.3 2017 $53.1 $82.5 2018 Actuals 2019 Source: Company information and management (1) Based on the mid-point of our guidance range for the year ended December 31, 2021, as disclosed in our May 5, 2021 Form 8-K. $99.9 2020 Annual AEBITDA Growth Trend Consistent Margin Expansion Driven by Upland One operating platform and scale efficiencies Adjusted EBITDA expansion from 3% at IPO to 32% today (1) and should continue to expand from simple operating leverage with increased scale over the next 5 years Investing in Go-to-Market team across Sales, Marketing, and Customer Success starting in 2020 and seeing full impact on margin in 2021 20#21Free Cash Flow Trend Growth Drivers Free Cash Flow (1) ($ in millions) 4 Year CAGR: 81%(2) Accretive acquisitions AEBITDA margin expansion from 17% in 2016 to 32% in 2021(3) Increasing annual acquisition activity masked growing FCF until 2020 Due to the nature of our compounding business model, with conservative assumptions, our annual FCF growth rate could exceed our total revenue growth rate target of 15% while increasing ROIC and ROE over the next 5 years $3.2 2016 $7.3 $6.4 $11.0 $34.5 2017 2018 2019 2020 Actuals Source: Company information and management (1) See definition of FCF and non-GAAP reconciliation table in appendix. (2) Calculated based on FCF for the years ended December 31, 2016 and 2020. (3) Based on the mid-point of our guidance range for the year ended December 31, 2021, as disclosed in our May 5, 2021 Form 8-K. 21#22U Appendix 22 22#23Acquisition Related Expenses Are Temporary Example Mix of Acq Related Expenses Example Timing of Acq Related Exp on P&L for Each Acq . Legal, accounting, tax diligence experts Banking fees Indemnity insurance M&A bonuses Restructuring & Transaction Transformation costs Non-People Costs Restructuring & Transformation People Costs Office lease terminations Vendor cancellations 50% Datacenter lift & shift 45% 40% 35% 30% 25% 20% 15% 10% 5% 0% Expenses Eliminated after 4 Qtrs Severance Transitional personnel compensation • Temporary transitional contractors Marketing conversions Q1 Q2 Q3 Q4 Note: Expense recognition timing varies based on the timing of the close of the acquisition transaction within the initial calendar quarter and when each type of expense is incurred. Examples: acquisition transaction costs are generally expensed when the acquisition closes; people costs are expensed as compensation is earned over time; severance expense is recognized in the period that termination is communicated to the employee; and lease termination costs are expensed in the period when the lease is vacated. 23#24Theoretical AEBITDA to FCF Bridge (FTM) Before Acquisition Related Expenses in Millions $120 $100- $80 $60 $40 $20 $97 $(30) $(5) $(8) $(1) $- AEBITDA (¹) Cash Interest (2) Cash Taxes (3) Cash Commissions (4) Capex (5) Source: Company information and management (1) Based on the midpoint of full year 2021 guidance in the May 5, 2021 Form 8-K. (2) Annual net cash interest based on $532MM of gross debt outstanding at 5.4% interest rate. (3) Annual cash taxes estimated based on cash taxes disclosed in the supplemental information of the Statement of Cash Flows for full year 2020 in the February 25, 2021 10-K and forecasting additional cash taxes for recent acquisitions. (4)Estimated annual sales commissions to be paid, net of amortization of deferred commissions (i.e. annual increase in prepaid sales commissions). (5)Annual capital expenditures for purchases of plant, property, and equipment based on full year 2020 in the February 25, 2021 10-K. Note: The above bridge is representative of FCF prior to any Acquisition related expenses, which vary based on acquisition activity. See definition and reconciliation of FCF as non-GAAP measure in the appendix. Note: This chart is for illustrative purposes only, does not constitute guidance and is based solely on assumptions. There can be no assurance that these illustrative amounts will represent future results. For example, annual cash taxes are estimated with high level assumptions and have not been determined by bottoms-up analysis around taxable income by jurisdiction and tax NOL usage over time. Similarly, cash interest could change with debt levels, cash commissions are dependent upon levels of future bookings, capex could vary, and acquisition related expenses vary based on the size and timing of acquisitions. 24 24#25Organic Growth GAAP Recurring Revenue Operating assets owned for full prior year comparison period, excl. divested/sunset assets UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K Upland Software, Inc. (Exact name of registrant as specified in its charter) Comparison of Years Ended December 31, 2020 and December 31, 2019 "...Therefore, subscription and support revenue from our Organic Business increased by $20.0 million...” Deferred revenue discount can inflate reported organic growth Disclosed in 10-Q/K's and tied out by external independent auditors “...subscription and support revenue related to our organic business increased by $20.0 million." Source: Company Information Note: Above screen shot from the MD&A Section of our 2020 Form 10-K filed on February 25, 2021. 25 25#26UplandOne Cloud Platform Customer Experience Management Single Sign On 28+ Products Enterprise Sales & Marketing Unified User Interface Document Workflow Integrations powered by Dell Boomi Enterprise-Grade Cloud Platform Project & IT Management Unified Analytics boomi Tamazon web services Linked in ORACLE servicenow. salesforce Third-Party Platforms Microsoft SAP C. CONCUR infor 26 26#27Acquisitions To Date FEB PowerSteering 2012 Project Portfolio Management JAN LeadLander FEB Tenrox 2012 Professional Services Automation NOV EPM Live 2012 Project & Work Management MAY FileBound 2013 Document & Workflow Automation NOV ComSci 2013 IT Financial Management DEC Clickability 2013 Enterprise Web Content Management NOV Eclipse PPM 2014 Project & Work Management DEC Mobile Commons 2014 Enterprise Mobile Messaging & SMS NOV Ultriva 2015 Supply Chain Management 2016 Website Visitor Analytics & Reporting MAR Hipcricket 2016 Enterprise Mobile Messaging & SMS MAY API 2016 Document & Workflow Automation JAN Omtool (AccuRoute) 2017 Secure Document Capture & Fax APR RightAnswers 2017 Enterprise Knowledge Management JUL Waterfall 2017 Enterprise Mobile Messaging & SMS NOV Qvidian 2017 RFP & Sales Proposal Automation MAR InterFAX 2018 Enterprise Cloud-Based Fax JUN RO Innovation 2018 Customer Reference & Sales Enablement 27#28Acquisitions To Date (continued) OCT Rant & Rave 2018 DEC 2018 Cloud-Based Customer Engagement Adestra Email Marketing Automation & Analytics APR Post-Up 2019 Email Marketing Automation & Analytics MAY Kapost 2019 Content Operations Platform AUG Cimpl 2019 Telecom Expense Management OCT InGenius 2019 Contact Center Productivity OCT Altify 2019 Customer Revenue Optimization FEB Localytics 2020 Mobile Application Personalization JAN Second Street 2021 Contests and Interactive Content MAR BlueVenn 2021 Customer Data Platform 28#29To supplement our consolidated financial statements, which are prepared and presented in accordance with GAAP, we use the following non- GAAP financial measures: Adjusted EBITDA, non-GAAP net income (loss), non-GAAP net income (loss) per share and free cash flow. We use these non-GAAP financial measures for financial and operational decision-making and as a means to evaluate period-to-period comparisons. Our management believes that these non-GAAP financial measures provide meaningful supplemental information regarding our performance and liquidity by excluding certain expenses and expenditures that may not be indicative of our recurring core business operating results, such as our revenues excluding the impact for foreign currency fluctuations or our operating performance excluding not only non-cash charges, but also discrete cash charges that are infrequent in nature. We believe that both management and investors benefit from referring to these non-GAAP financial measures in assessing our performance and when planning, forecasting, and analyzing future periods. These non-GAAP financial measures also facilitate management's internal comparisons to our historical performance and liquidity as well as comparisons to our competitors' operating results. We believe these non-GAAP financial measures are useful to investors both because they allow for greater transparency with respect to key metrics used by management in its financial and operational decision-making and they are used by our institutional investors and the analyst community to help them analyze the health of our business. For a reconciliation of these non-GAAP financial measures to the most directly comparable GAAP financial measures, see the tables provided below in this presentation. We are unable to reconcile any forward-looking non-GAAP financial measures to their directly comparable GAAP financial measures because the information which is needed to complete a reconciliation is unavailable at this time without unreasonable effort. Upland defines Adjusted EBITDA as net loss, calculated in accordance with GAAP, plus depreciation and amortization expense, interest expense, net, other expense (income), net, loss on debt extinguishment, provision (benefit) for income taxes, stock-based compensation expense, acquisition-related expenses, and purchase accounting adjustments for deferred revenue. Upland defines Adjusted EBITDA margin as Adjusted EBITDA divided by total revenue. Upland defines free cash flow as GAAP operating cash flow less purchases of property and equipment. U Non-GAAP Financial Measures 29#30Adjusted EBITDA Reconciliation to Net Income (Loss) (in Millions) 2016 2017 2018 2019 2020 Net Income (Loss) $(13.5) $(18.7) $(10.8) $(45.4) $(51.2) Depreciation and amortization expense 9.8 11.8 21.3 34.6 47.1 Interest expense, net 2.8 6.6 13.3 22.3 31.5 Other expense (income), net 0.7 (0.3) 1.8 3.2 0.1 Loss on debt extinguishment 2.3 Provision for (benefit from) income taxes 1.5 1.3 (9.8) (6.8) (4.2) Stock-based compensation expense 4.3 10.0 14.1 25.8 41.7 Acquisition-related expense 5.6 15.1 18.7 39.7 27.1 Nonrecurring litigation expense 0.0 Purchase accounting deferred revenue discount 1.4 4.5 4.5 6.8 7.8 Adjusted EBITDA $12.6 $30.3 $53.1 $82.5 $99.9 Source: Company Information We define Adjusted EBITDA as net loss, calculated in accordance with GAAP, plus depreciation and amortization expense, interest expense, net, other expense (income), net, loss on debt extinguishment, provision (benefit) for income taxes, stock-based compensation expense, acquisition-related expenses, and purchase accounting adjustments for deferred revenue. We believe that Adjusted EBITDA provides useful information to management, investors and others in understanding and evaluating our operating results; however, Adjusted EBITDA should not be considered as an alternative to net loss or any other measure of financial performance calculated and presented in accordance with GAAP and has important limitations as an analytical tool, including that other companies might calculate Adjusted EBITDA or similarly titled measures differently. Because of these limitations, you should consider Adjusted EBITDA together with other financial performance measures, including various cash flow metrics, net loss and our other GAAP results. Above is a reconciliation of Adjusted EBITDA to net income (loss), the most directly comparable GAAP measure. 30#31GAAP Operating Cash Flow Reconciliation to Free Cash Flow (in Millions) 2016 2017 2018 2019 2020 Net Cash provided by Operating Activities $3.9 $7.7 $7.3 $12.1 $35.6 Less: Purchase of property and equipment $(0.7) $(0.4) $(0.9) $(1.0) $(1.1) Free Cash Flow $3.2 $7.3 $6.4 $11.0 $34.5 Upland defines free cash flow as GAAP operating cash flow less purchases of property and equipment. 31