Squarespace Investor Day Presentation Deck

INVESTOR DAY HISTORICAL KPI's TOTAL Unique subscriptions (in thousands) Total bookings (in thousands) ARRR (in thousands) ARPUS Adjusted EBITDA (in thousands) Unlevered free cash flow (in thousands) GMV (in thousands) YOY Growth Unique subscriptions Total bookings ARRR ARPUS Adjusted EBITDA Unlevered free cash flow GMV SQUARESPACE 1Q 2018 2,127 $ 107,553 $379,907 $171 $6,547 $36,325 2Q 2018 2,210 $ 105,782 $ 381,007 $173 $31,106 3Q 2018 2,274 $ 106,267 $ 391,968 $175 $ 29,260 $11,240 $ 22,257 $ 305,018 $329,600 $325,284 4Q 2018 2,336 $ 107,324 $425,849 $ 178 $7,592 $13,083 1Q 2019 2,436 $ 126,158 $460,384 $ 179 $11,703 $ 42,886 $401,639 $400,700 15% 17% 21% 5% 79% 18% 31% 2Q 2019 ¹ (*) 2,579 $ 125,771 $478,699 $ 180 $37,118 $29,570 $ 522,079 17% 19% 26% 4% 19% 163% 58% 3Q 2019 2,667 $129,616 $495,364 $185 $ 30,464 $ 28,824 $ 506,714 17% 22% 26% 6% 4% 30% 56% 4Q 2019 ² 2,984 $ 132,873 $549,156 $181 $ 18,339 $ (6,709) $613,702 28% 24% 29% 2% 142% -151% 53% 1Q 2020 3,178 $155,868 $556,266 $183 $1,190 $ 53,364 30% 24% $612,590 $1,028,947 21% 2% -90% 24% 53% 2Q 2020 All quarterly data unaudited. KPI definitions and a reconciliation from GAAP to non-GAAP can be found in the following slides 1. Acquired Acuity 2. Acquired Unfold 3. Acquired Tock 3,422 $ 167,425 $605,917 $182 $ 39,505 $ 47,270 33% 33% 27% 1% 6% 60% 97% 3Q 2020 3,538 $ 168,861 $ 650,420 $ 188 $ 40,613 $45,194 33% 30% 31% 2% 33% 57% 4Q 2020 97% 3,656 $172,585 $ 709,062 $ 186 $ 35,358 $6,611 $999,872 $1,255,832 $1,225,988 $ 1,440,442 $1,376,159 23% 30% 29% 3% 93% -199% 1Q 2021 105% 3,794 $ 198,947 $754,206 $190 $ 11,097 $ 51,782 19% 28% 36% 4% 831% -3% November 2021 100% 2Q 2021 3 3Q 2021 3,937 $206,645 $777,940 $ 193 $ 42,640 $ 10,254 $ 47,251 15% 23% 28% 6% 8% 4,016 $ 205,885 $788,622 $198 $38,393 -78% 40% 116 13% 22% 21% 5% -5% 5% 38%

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