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Annual 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

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