Upwork Investor Presentation Deck

Enterprise at a Glance As of March 31, 2022 Enterprise Revenue ($M) $10 $8 $6 $4 $2 $0 $4.1 24% $4.5 19% Ⓒ2022 Upwork Inc. $5.2 39% $6.4 47% Q1'22 Investor Presentation $7.0 69% Enterprise Revenue $8.5 April 2022 88% $8.9 Note: See appendix for the definition of Enterprise Revenue and Enterprise Clients. 71% . YOY Growth $10.5 65% Q1'20 Q2'20 Q3'20 Q4'20 Q1'21 Q2'21 Q3'21 Q4'21 Q1'22 $10.8 55% New Enterprise Clients 40 30 20 10 0 8 75% -27% 14 75% 14 18 64% Q1'20 Q2'20 Q3'20 Q4'20 200% 24 New Enterprise Clients 29 107% 34 143% Q1'21 Q2'21 Q3'21 32 78% Q4'21 YOY Growth 32 33% Q1'22 25

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