Squarespace Investor Day Presentation Deck

INVESTOR DAY November 2021 DISCLAIMER This presentation may include forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995. Any statements made in this presentation that are not statements of historical fact, including statements about beliefs and expectations of Squarespace, Inc. (the "Company", "we" or "our") are forward-looking statements and should be evaluated as such. Forward-looking statements include, but are not limited to, statements about the Company's outlook for the fourth fiscal quarter and the full fiscal year ending December 31, 2021, the Company's market position, potential market opportunities, and long-term financial targets. Forward-looking statements generally relate to future events or the Company's future financial or operating performance. These statements are often, but not always, made through the use of words or phrases such as "may," "should," "could," "predict," "potential," "believe," "will likely result," "expect," "continue," "will," "anticipate," "seek," "estimate," "intend," "plan," "projection," "would" and "outlook," or the negative version of those words or phrases or other comparable words or phrases of a future or forward-looking nature. The Company bases these forward-looking statements on its current expectations, plans and assumptions that the Company has made in light of its experience in the industry, as well as its perceptions of historical trends, current conditions, expected future developments and other factors the Company believes are appropriate under the circumstances at such time. As you read and consider this presentation, you should understand that these statements are not guarantees of future performance or results. The forward-looking statements are subject to and involve risks, uncertainties and assumptions, and you should not place undue reliance these forward-looking statements. Althou the pany believes that these forward-looking statements are based on reasonable assumptions at the time they are made, you should be aware that many factors could affect the Company's actual results or results of operations and could cause actual results to differ materially from those expressed in the forward-looking statements. Factors that may materially affect such forward-looking statements include: our ability to attract and retain customers and expand our customers' use of our platform; our ability to anticipate market needs and develop new or enhanced solutions to meet those needs; our ability to compete successfully in our industry against current and future competitors; the impact of the COVID-19 pandemic and the associated economic uncertainty on us, our customers and their users; our ability to manage growth and maintain demand for our solutions; our ability to protect and promote our brand; our ability to successfully identify, manage and integrate any existing and potential acquisitions; our ability to hire, integrate and retain highly skilled personnel; our ability to adapt to and comply with existing and emerging regulatory developments, technological changes and cybersecurity needs; our ability to establish and maintain intellectual property rights; and our ability to manage expansion into international markets. Further information on risks that could cause actual results to differ materially from forecasted results are included in the Company's filings with the SEC, including the Company's final prospectus filed on May 19, 2021 with the SEC and Amendment No. 1 to the Company's Quarterly Report on Form 10-Q, filed on November 15, 2021 with the SEC. The Company undertakes no obligation to update or revise any forward-looking statements, whether as a result of new information, future events or otherwise, except as required by applicable law. All written and oral forward-looking statements made in connection with this presentation attributable to the Company or persons acting on the Company's behalf are expressly qualified in their entirety by the above paragraph. This presentation contains non-GAAP financial measures such as adjusted EBITDA and unlevered free cash flow. These measures are not prepared in accordance with generally accepted accounting principles in the United States of America ("GAAP") and have important limitations as analytical tools. Non-GAAP financial measures are supplemental, should only be used in conjunction with results presented in accordance with GAAP and should not be considered in isolation or as a substitute for such GAAP results. Refer to the Appendix of this presentation for a reconciliation of each non-GAAP financial measure to the most directly comparable financial measure calculated and presented in accordance with GAAP. This presentation contains additional trademarks, tradenames, and service marks of other companies that are the property of their respective owners. Certain monetary amounts, percentages and other figures included in this presentation have been subject to rounding adjustments. Certain other amounts that appear in this presentation may not sum due to rounding. SQUARESPACE 3

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