Upwork Investor Presentation Deck

Our Compelling Margin Structure High and expanding gross margins Industry-leading investment levels in R&D to extend competitive moats Opportunities for leverage in R&D and G&A Will invest aggressively in sales and marketing to drive growth and maximize economic value added Note: Numbers are non-GAAP. Non-GAAP here excludes SBC, amortization, non-cash charitable donations, and certain incremental expenses associated with our humanitarian response efforts in response to Russia's invasion of Ukraine. All numbers reflect depreciation expense, except for adjusted EBITDA. Ⓒ2022 Upwork Inc. Q1'22 Investor Presentation April 2022 % of Revenue FY2018 Total Gross Margin R& S&M G&A Transaction Losses Adjusted EBITDA 68% 21% 28% 16% 2% 1% FY2019 71% 19% 31% 18% 1% 2% FY2020 72% 20% 34% 15% 1% 4% FY2021 73% 20% 35% 14% 1% 4% Q1'22 73% 21% 39% 13% 2% 0% LT Target 80-85% 15-20% 20-25% 8-10% 1-2% 30-35% 26

View entire presentation