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AUGUST 2020InvestorPresentation1 2020 Upland Software, Inc.

Safe Harbor StatementThis presentation includes “forward-looking statements,” which are subject to substantial risks, uncertainties and assumptions, subject to the safe harbor provisions of the PrivateSecurities Litigation Reform Act of 1995. Accordingly, you should not place undue reliance on these forward-looking statements. Forward-looking statements include any statement thatdoes not directly relate to any historical or current fact and often include words such as "believe," "expect," "anticipate," "intend," "plan," “assume,” “assumption,” “forecast,” "estimate,""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 toachieve, 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 todeliver 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 integrateacquisitions 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 tomaintain 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 tochanging market conditions and competition; our ability to successfully enter new markets and manage our international expansion; fluctuations in currency exchange rates; theoperation 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 theSecurities and Exchange Commission (the "SEC"), including Upland's most recent 10-K, filed with the SEC on March 2, 2020. Additional information will also be set forth in Upland'sfuture 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 theseforward-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 representingthe 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.2 2020 Upland Software, Inc.

PresentersJack McDonaldMike HillFounder, Chairman, and CEOCFO Led two successful NASDAQ IPOs (UPLD PRFT) Created 2BN in shareholder / enterprise value across companies Led PRFT (1999 – 2010) from startup to 250MM global IT consultingleader Consistent value creation track record as public companyChairman / CEO Executed 45 successful technology acquisitions as CEO in 20 years3 CFO of PRFT (2004-2007) from 30MM to over 200MM annualrevenue run-rate Executed as CFO 35 successful technology acquisitions across threecompanies Consistent value creation track record as public company CFO Started career at Ernst & Young LLP (1991 – 1999) 2020 Upland Software, Inc.

ProductStrategy4 2020 Upland Software, Inc.

We transform howorganizations sell,engage, and manage 5 2020 Upland Software, Inc.

with proven cloud toolsthat deliver value quicklywithout re-platforming orbuilding from scratch.6 2020 Upland Software, Inc.

Tools for Digital TransformationCustomer ExperienceManagementDocumentWorkflowFront OfficeBack OfficeEnterprise Sales &Marketing7Project &IT Management 2020 Upland Software, Inc.

Driving Value Across the EnterprisePowering more effectivecall center interactionsand delivering MMs inannual savingsCustomerExperienceDocumentWorkflowMobile Mark etingSecure Document CaptureEmail Mark etingEnterprise Cloud FaxVoice of CustomerKnowledge ManagementDocument & Work flowAutomationCall Center OperationsEnterpriseS&MAccount ManagementOpportunity ManagementReducing time to marketfor new website and socialmedia content8RFP AutomationCustomer AdvocacyFinancialServicesCustomerProject & ITManagementIT Financial ManagementTelecom Expense ManagementProject & Portfolio ManagementProviding project visibilityand management forthousands of usersacross the businessProfessional Services AutomationContent Operations 2020 Upland Software, Inc.

Unified UplandOne Cloud Platform20 ProductsCustomer ExperienceManagementSingle Sign OnEnterprise Sales& Marketing Project &IT ManagementUnified User Interface DocumentWorkflowUnified AnalyticsIntegrations powered by Dell BoomiEnterprise-Grade Cloud PlatformThird-Party Platforms9 2020 Upland Software, Inc.

ProductStrategy10Digital transformationis an ongoing journeyrequiring provenproducts and along-term partnerWe provide plugand-play cloudsolutions that don’trequire building fromscratch or replatformingOur tools fortransformationsolve multiplepain points anddeliver immediatevalue 2020 Upland Software, Inc.

Market &Growth Strategy11 2020 Upland Software, Inc.

Digital Transformation is Driving DemandEnterprises challenged to resolve key pain pointsCustomer Expectations Continue to GrowRise of the customer experience economy – CX as today’s competitive battlegroundProliferation of customer touchpoints driving more complexity and more siloed interactionsDisparate Data and Inefficient Processes Create BottlenecksManual, time-intensive processes as the status quoComplex, intertwined web of paper documents and digital workflowsOperational Complexity Creates Cost and Productivity ChallengesLack of coordination and alignment directly hurting the top and bottom lineLimited visibility into project budget and status driving bloated costs12 2020 Upland Software, Inc.

KnowledgeManagement 1.9BCreating MultipleAttractive MarketsProject & FinancialManagement 4.7BCXM 8.5B 25BTAMDocumentAutomation 6.5BSources:Gartner Enterprise Software Forecast Q2 2020Gartner Market Share All Software Markets Worldwide 2019https://www.openpr.com/news/2000791/knowledge- management-software-mar kets.c om/M arket-Reports/cus tomer-experience-management-cem-mar ket-543.htmlhttps://aragonresearch.com/sal es-engagement/13SalesEnablement 3B 2020 Upland Software, Inc.

Upland’s Products Well PositionedPlug and play time to value with enterprise scaleBeat small pointsolution vendors scale & resources to deliverproduct portfolioincumbent positionstrong financialsReplace homegrownapps & toolsExtend largeenterprise platforms buy vs. build critical functionalityapproved platform partnerfaster time to valueleverage existing infrastructure plug & playeliminate costly maintenancemodernize experiencemigrate to cloudExpansion and Cross Sell Motion14 2020 Upland Software, Inc.

Upland Growth FlywheelBuild product portfolio andadd blue chip customersthrough accretiveacquisitionsProfessionalize operationsvia UplandOnetransformation playbookExpand sales distributionto 10,000 Uplandcustomers15 2020 Upland Software, Inc.

The Consolidation OpportunityFueled by continued VC cloud investmentsGrowing pipeline of targetsITSM 318 billion invested by VCs since2002(1) - majority in last 5 yearsSalesEnablementDocumentAutomationCXMWe seek out “orphaned”VC InvestmentsProven, disciplined model26 acquisitions to date of high quality,subscale, thematic cloud products at5-8x pro forma AEBITDAIPO orStrategicExitConsolidationOpportunityOut ofBusinessSource: Company information and management(1) Pw C/CBInsights MoneyTree data for Q1 2002 to Q4 2019, filtered by Sector(Software and Internet) and Stage (Seed / Angel, Series A / B / C / D / E , or Other).16Accretive acquisitionsProduct portfolio and customer baseexpansion, operating leverage throughscale, AEBITDA per share 2020 Upland Software, Inc.

M&A Playbook: Goals & TargetsGoals & Track RecordStrategic FitFinancial Fit Cloud-native andcomplementsolutions customersneed 5- 25MM Revenue 90% NDRR 70% Gross MarginsAdd to our Fortune2000 and majormid-size customerbase Average ARR perMajor Account 25K 10-20% OrganicGrowth 5-8x Pro Forma Adj.EBITDA(1) Innovate throughacquisitionAdd 25- 50MMrevenue run-rate peryear 26 acquisitions todate @ 0.9x-3.5x revsStrong reputation /pipeline US, Canada, EMEATypical Challenges Access to growthcapital Inefficient productroadmap and R&D Lack scale to buildcost effectiveenterprise salesdistributionSource: Company inf ormation and management(1) See Appendix f or def inition of Adjusted EBITDA.17 2020 Upland Software, Inc.

Transforming Operations with UplandOne ModelScalable with high margins and high customer satisfaction100% CustomerSuccess CultureEnterprise GradeDeliveryCustomer-DrivenInnovation via M&AOutsourcing andOffshoringAccount BasedSales DistributionProgrammatic customeraccount managementAWS, global customersupport and servicesAccelerates product roadmapand cross-sellingTap global labor staff withstars at fraction of priceTargeting key verticals andbusiness functionsSatisfied CustomersHigher Margins97%33%Net Dollar Retention Rate (1)Adjusted EBITDA margin (2)Source: Company inf ormation and management(1) As disclosed in our Form 10-K f or the y ear ended December 31, 2019.(2) As disclosed in our Form 10-Q f or the quarter ended June 30, 2020. See our Form 10-Q f or the quarter ended June 30, 2020 f or def inition and reconciliation of Adjusted EBITDA.18 2020 Upland Software, Inc.

Sales Distribution to 10,000 CustomersFinancial ServicesManufacturing, Industrial1,600 Major accounts 160K ARRGovernment, Nonprofit, EducationCorporate Services1.XTechnologyHealthcareTelecom & MediaConsumer, RetailAverage productsper accountNew TeamEvolving cross sellingmotions at product,function, industry levels19 2020 Upland Software, Inc.

Powering DigitalTransformationMassive, GrowingMarketPowerful GrowthFlywheelCloud tools that delivervalue quickly without replatforming or buildingfrom scratchDriven by cloud, digitaltransformation, and VCinvestment tailwindsAccretive M&A OperatingModel Sales DistributionAttractive FinancialModelCapital and TaxEfficientExperiencedLeadershipHigh growth, recurringrevenue, high margin model 1MM/yr CAPEX and 200MM NOLsExperienced team drivingvalue creation throughprudent capital stewardshipInvestmentHighlights20 2020 Upland Software, Inc.

FinancialOverview21 2020 Upland Software, Inc.

FinancialHighlights44% 94%97%Revenue growthCAGRRecurringRevenue(2)Net DollarRetention Rate(3)’16A-’19A(1)(1) Based on revenue as disclosed in our Form 10-K for theyear ended December 31, 2019 and 10-K for the yearended December 31, 2016.33%Adjusted EBITDAmargin(4)Target 40% at scale22Strong free cashflow conversionDisciplineduse of leverage(2) Recurring revenue is also know n as subscription andsupport revenue; based on subscription and supportrevenue as disclosed in our Form 10-Q for the quarterended June 30, 2020.(3) As disclosed in our Form 10-K for the year endedDecember 31, 2019.Low CAPEX, tax efficientTarget Leverage 3.0 - 4.0x(4) As disclosed in our Form 10-Q for the quarter endedJune 30, 2020. See our Form 10-Q for the quarterended June 30, 2020 for definition and reconciliation ofAdjusted EBITDA. 2020 Upland Software, Inc.