Slide 1: Investor Presentation
© ere Investor Presentation July 2025
Slide 2: Forward-looking statements
This presentation contains "forward-looking statements" within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchange Act of 1934, as amended. Forward-looking statements generally relate to future events or our future financial or operating p
Slide 3: Contents
© Bele)(-e)i Contents + ++ +++ t++t+t+ ++++++ +4+++44 +++4+4+4++ pope pp Recent Updates Company Overview Products Customers Market Opportunity Management Team Financial Overview Appendix - Reconciliations, etc.
Slide 4: Recent Updates
© Recent Updates Notes: Completed Divestitures to focus our business on markets where we have the strongest competitive advantage, higher margins, and higher growth Completed build out of our India offshore development center, enabling efficient product innovation Enhanced product performance and ca
Slide 5: Company Overview
Company Overview Knowledge & Content Management Upland By the Numbers =! ili cy <39 . Upland provides Al-powered knowledge & content $193 million 2.5%+ . 1,100+ 3% 7 loud soft han 1,100 FY25E Core Total 2H25E Core Organic Enterprise Top Customer % management cloud software to more than 1; Revenue Gr
Slide 6: Upland's AI-Powered Product Portfolio
Upland’s Al-Powered Product Portfolio Our products solve complex business problems and provide a trusted path forward for Al adoption. Knowledge and Content Management Lifecycle oO
Slide 7: Knowledge & Content Management Use Cases
Knowledge & Content Management Use Cases CONNECTED ENTERPRISE KNOWLEDGE Enterprise Search Al-Enablement Co-Pilot Content Contribution Federated CC Knowledge Self-Service CC Portals Cu) Solving complex enterprise business problems and delivering tangible ROI ° DOCUMENT AUTOMATION S&C Questionnaire Re
Slide 8: Customer Validation
[ Customer Validation © Ba insight 'G) PARI K 012 “Powerful indexing and federated search tools" © interFax PAA AA 0228 “The most capable and efficient cloud fax service to share all your documents.” Cu) Panviva PARAM 102.200 “Panviva fundamentally transformed our KM" © avidian Pee Ae We Be 0020202
Slide 9: Recurring Revenue
te) ~88 Recurring Revenue from Major Enterprise Accounts") ~$137K Average annual spend per Enterprise Account (ARR) 99% NDRR YE24 Core Only” 1100+ Enterprise Accounts” Financial Services oldman) JPMorganChase © PAYCHEX Government, Nonprofit, Education DeSoto OXFORD Technology [| Hewlett Packard Ente
Slide 10: Favorable Market Dynamics
Favorable Market Dynamics Supporting Long-Term Growth . Knowl Content Services? owledge ») Knowledge Management software helps $5B TAM Management‘ organizations capture, organize, share, and 3 (3) $6B TAM analyze knowledge to improve decision- 15% Growth 15% Growth® making and collaboration. Content
Slide 11: Experienced Management Team
Experienced Management Team f} Dan Doman Mike Hill Rick Rinewalt Chief Product & Chief Financial Chief Technology Operating Officer Officer Officer 4 ~ Jack McDonald Founder, Chairman, & CEO Michael Frannea Jantzen McLellan Jen Verzal SVP Marketing & Sales SVP Business SVP Human Development Operatio
Slide 12: Financial Highlights
Financial Highlights Growth at Scale Highly Predictable and Strong Visibility Robust Profitability ng Cash Flow Characteri Debt Paydowns and Net Leverage Notes: ~$193 million 2.5%+ FY25E Core Total Revenue 2H2SE Core Organic Growth Rate 99% 93% YE24 Net Dollar Retention Rate Core Only FY25E % Recurr
Slide 13: Growth Goals
Core Total Revenue Trend ($ in millions) Core Organic Growth Rate: fa fe ea Notes: + See Appendix for Guidance & Forecast Disclaimer, and definitions of Core Total Revenue, Core Organic Growth Rate, Divestitures, Sunset Assets, and NDRR, and for reconciliation of Non-GAAP financial measures to the m
Slide 14: Growth Goals
Growth Goals Core Sunset Assets Divestitures • • •
Slide 15: AEBITDA Growth and Margin Expansion Goals
AEBITDA Growth and Margin Expansion Goals •
Slide 16: Excludes Depreciation & Amortization and Stock-Based Compensation
Excludes Depreciation & Amortization and Stock-Based Compensation
Slide 17: Appendix
Appendix
Slide 18: Debt Summary
Debt Summary ($ in millions) July 2025 Sept. 30, 2025 June 30, 2025 Post- Forecast Refinancing) Total Gross Debt) 258.1 240.0 240.0 3.7x YE25SE Target Less: Unrestricted Cash 41.0 26.0 18.0 Net Leverage Total Net Debt 2171 714.0 222.0 Expeching)tg continue to De-lever thereafter (1) New credit facil
Slide 19: Reconciliation of Total Revenue to Core Total Revenue
Reconciliation of Total Revenue to Core Total Revenue ($ in millions) Year Ended December 31, 2024 2023 GAAP - based Total Revenue 275 298 Less: Revenue from Sunset Assets 12 22 72 85 Revenue from Divestitures Core Total Revenue Source: Company Information. Notes: + See Appendix for definitions of C
Slide 20: Reconciliation of Total Revenue to Core Organic Revenue
Reconciliation of Total Revenue to Core Organic Revenue ($ in millions) Year Ended December 31, 2023 2024 Compare 2023 2022 Total Revenue 2748 2979 2979 3173 Less: Perpetual license revenue 58 61 61 7.0 Professional services revenue 83 10.2 10.2 125 Subscription and support revenue 121 14 214 262 fr
Slide 21: Reconciliation of Selected Non-GAAP Measures
Reconciliation of Selected Non-GAAP Measures Year Ended December 31, 2024 ($ in millions) GKAP% oF Non-GAAP % GAAP Total Adjustments Note Non-GAAP of Total Revenue Revenue Total revenue 275 - 275 Cost of revenue: 76 28% 0) @ 66 24% Subscription and support 5 2% - 5 2% Professional services and other
Slide 22: Reconciliation of Selected Non-GAAP Measures
Reconciliation of Selected Non-GAAP Measures Year Ended December 31, 2023 ($ in millions) Total revenue Cost of revenue: Subscription and support Professional services and other GAAP Gross profit and gross margin %/Non-GAAP Gross profit and Non-GAAP gross margin % Operating expenses: Sales and marke
Slide 23: Guidance & Forecast Disclaimer; Definitions and Non-GAAP Financial Measures
Guidance & Forecast Disclaimer; Definitions and Non-GAAP Financial Measures Guidance and ForecastDisclaimer: FY25E Total Revenue, AEBITDA, AEBITDA Margin, Recurring Revenue are per guidance mid-points. Gross Margin and AEBITDA Margin is calculated based on Total Revenue. FY25E Core Organic Growth Ra