#1INVESTOR DAY un November 2021 LLLL SQUARESPACE Investor Day#2INVESTOR DAY AGENDA SQUARESPACE 01 Company Overview 02 Growth Levers 03 Product Updates 04 Unfold 05 Financials 06 Appendix November 2021 2#3INVESTOR 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#4INVESTOR DAY COMPANY SQUARESPACE November 2021 OVERVIEW 4#5Q3 2021 EARNINGS PRESENTATION SQUARESPACE Squarespace exists to help people with creative ideas stand out and succeed. November 2021#6A Q3 2021 EARNINGS PRESENTATION SQUARESPACE We seek to enable millions to build a brand and transact with their customers across an impactful and beautiful online presence. November 2021#7INVESTOR DAY SQUARESPACE AT A GLANCE ₁ AS OF 09/30/21 4.0M Unique Subscriptions 2 LTM AS OF 09/30/21 93% Subscription-Based Revenue U SQUARESPACE LTM AS OF 09/30/21 LTM AS OF 09/30/21 LTM 09/30/21 VS. 09/30/20 $749M $210M 29% Commerce Revenue Total Revenue Growth Total Revenue LTM AS OF 09/30/21 84% Gross Profit Margin 9-MO. 9/30/21 VS. 9/30/20 67% Commerce Rev. Growth Rate LTM AS OF 9/30/21 15% uFCF Margin 3 1. Based on Unaudited Financial Statements. 2. Unique subscriptions represent the number of unique sites, standalone scheduling subscriptions and Unfold (social) subscriptions, as of the end of a period. A unique site represents a single subscription and/or group of related subscriptions, including a website subscription and/or a domain subscription, and other subscriptions related to a single website or domain. Every unique site contains at least one domain subscription or one website subscription. 3. Unlevered free cash flow (UFCF) is a non-GAAP financial measures. For a reconciliation of this non-GAAP financial measure to the most directly comparable financial measure calculate in accordance with GAAP, please see the Appendix November 2021 7#8INVESTOR DAY OUR STORY valor thong (b) 2010 First institutional Investment from Accel and Index Ventures SQUARESPACE 2012 Launched Squarespace 6 design system and surpassed 100 employees Stratton Co. Stratton Co offers an extensive selection of modern stationery-available bespoke or stock. 2013 Introduced Commerce offering 2015 Surpassed 500 employees and passed $100M in bookings 2016 Reached net income profitability 2019 Acquired Acuity Scheduling and Unfold 2020 Surpassed 1,200 employees and $665M in bookings November 2021 2021 Acquired Tock & Public Offering via Direct Listing 8#9INVESTOR DAY R ||| All-in-One Platform SQUARESPACE WHY SQUARESPACE? 20 Power with Simplicity Beautiful Design, Consistent Everywhere Sell Anything @ Built for Modern Use Cases November 2021 Customer Support 9#10INVESTOR DAY ALL-IN-ONE PLATFORM Single, integrated platform keeps data and brand assets consistent across digital channels SQUARESPACE Claim Your type to search. PRESENCE Websites & Domains Social (via Unfold Mobile App) Professional Email (via Google Workspace) Enterprise O COMMERCE Online Stores Scheduling & Appointments Member Areas Reservations & Events (via Tock) New Season Leather Goods MARKETING Campaigns SEO Analytics 11 Video Studio November 2021 10#11INVESTOR DAY GROWTH SQUARESPACE NAVELA November 2021 LEVERS 11#12INVESTOR DAY MARKET LANDSCAPE Large, Accelerating Market SQUARESPACE 1. 2. $350 B Total Global Web Tools Addressable Market 3 $180B "Traditional" Web Tools TAM 2 November 2021 Based on Unaudited Financial Statements. Source: Barclays, 2021. Includes domain registration, basic website (DIY), hosting, branded email, onsite purchases & checkout, 3rd party marketplace integration, payments, shipping labels, email and other marketing, social media content, and marketing 3. Source: Barclays, 2021. Traditional Web Tools TAM plus inventory management, pick-pack-ship & 3PL, POS devices & integration, accounting, tax, HR, IT ticketing, and other software solutions $749M Squarespace LTM 9/30/21 Revenue 1 12#13INVESTOR DAY SQUARESPACE COMMERCE November 2021 13#14INVESTOR DAY COMMERCE TIMELINE SHANON PLATT 2013 ONLINE STORES MANUAL SQUARESPACE MANUAL $24.99 Choose Appointmest Your Informa APRIL 2019 APPOINTMENTS JUNE 2019 EMAIL CAMPAIGNS Dipped Mist Cup Dipped Mist Cup Align and Flow d Join 200-Teacher Training 1 200-le Teacher Trag NOVEMBER 2020 MEMBER AREAS November 2021 MARCH 2021 RESERVATIONS & EVENTS Patio Reservation 14#15INVESTOR DAY COMMERCE GROWTH GMV (B) Commerce Rev. (M) SQUARESPACE 75% Commerce Revenue 2-Yr CAGR 69% GMV 2-Yr CAGR $1.4B $47M 2018 $2.0B $81M 2019 $3.9B $143M 2020 67% Commerce Rev. YoY 53% GMV YOY $2.6B $99M 9M 20 $4.0B $165M 9M 21 FY 2018 and all quarterly information is unaudited. See the Appendix for definitions. 75% Commerce Revenue 2-Yr CAGR 69% GMV 2-Yr CAGR ~10 year Commerce investment As GMV continues to increase, payments offering decision is expected in 2021 Scheduling revenue grew ~60% y/y in Q3 2021 and GMV grew ~80% November 2021 15#16INVESTOR DAY LONG TERM COMMERCE GOAL SQUARESPACE November 2021 >50% of Total Revenue from Commerce Related Activity 16#17INVESTOR DAY INTERNATIONAL EXPANSION SQUARESPACE November 2021 17#18INVESTOR DAY INTERNATIONAL REVENUE (IN MILLIONS) SQUARESPACE 30% International 2-Yr CAGR 31% Total Revenue (as of Q3 2021) % of Total Revenue الاسد International Rev. (M) 29% $113 2018 29% $142 2019 31% $191 31% Yo 2020 30% $136 9M20 31% $178 9M21 November 2021 18#19INVESTOR DAY INTERNATIONAL EXPANSION INTERNATIONAL Mostly English Non-US today 2018-2020 CAGR of 30% Run-Rate Revenue of $250M SQUARESPACE US REVENUE -69% INT'L REVENUE ~31% UPCOMING N SEPA Payment Method Launch in Q4 2021 Norwegian & Danish Site Support in 1H 22 ACCOUNT & SITE CREATION LANGUAGES ¹ English, German, Spanish, French, Italian, Portuguese, Dutch (Site Only), Swedish (Site Only) UK Localized Marketing Campaigns (Q3 2021) ACCEPTED CURRENCIES ² USD, AUD, GBP, EUR London Location Pending Amsterdam Location Pending 1. Account language refers to the ability to create or build a website. Site language refers to the translation of a website for the end-user 2. Accepted Currencies refers to those accepted to purchase Squarespace products or subscriptions. 3. Customer Currencies refers to those supported by our payment processors for our customers' customers CUSTOMER CURRENCIES ³ November 2021 USD, ARS, AUD, BRL, GBP, CAD, COP, CZK, DKK, EUR, HKD, INR, IDR, ILS, MYR, MXN, NZD, NOK, PHP, PLN, RUB, SGD, ZAR, SEK, CHF, or THB AUSTRALIA Localized Marketing Campaigns (Q3 2021) Sydney Location Pending 19#20INVESTOR DAY BESPOKE INTERNATIONAL CAMPAIGNS rn your dream business o a beautiful online store. Enchanted Orchards By Snow White START YOUR FREE TRIAL SQUARESPACE SQUARESPACE Turn your dream business into a beautiful online store. Shop About Contact ETERNAL EYES By Dracula START YOUR FREE TRIAL SQUARESPACE ROBERTO BERTOLUZZI About Schedule Contact Store DANCE FITNESS BY ROBERTO Private weekend sessions available. BOOK A CLASS November 2021 SQUARESPACE Mach deine Leidenschaft zu mithilfe eines Circle-Mitgl ÜBER MICH KUINGT SKATEBOARDS PRODUKT ÄNDERN NEU: KUNST- SKATEBOARDS nech 50Essionen k terechnet und handnummeget wonde HINZUFÜGEN WERDE TEIL VON CIRCLE 20#21INVESTOR DAY LONG TERM INTERNATIONAL GOAL SQUARESPACE >50% of New Website Subscriptions from International Markets November 2021 21#22INVESTOR DAY SQUARESPACE CIRCLE November 2021 22#23INVESTOR DAY CIRCLE EXPERT COMMUNITY 25,000 20,000 15,000 10,000 SQUARESPACE 5,000 2017 1-Year Active Members 2017-2020 2018 2019 2020 • Launched in 2016 • Drives ~8% of all new website subscriptions • Higher LTV and share of attached products • New Referral Program Launched in Oct 2021 • ~25K 1-Yr. Active Circle Members (2020) Active Circle Member represents a Circle Member who has created a new website in the last calendar year that subscribed after the user joined Circle. November 2021 23#24INVESTOR DAY LONG TERM CIRCLE GOALS SQUARESPACE 50K Active Circle Members (~25k as of Sept 30, 2021) November 2021 24#25INVESTOR DAY SQUARESPACE ENTERPRISE November 2021 25#26INVESTOR DAY ENTERPRISE CHUD SQUARESPACE Team formed in 2019; Initial products launched in 2020 November 2021 Current Offering o Volume -- Designed to streamline workflows to manage a large number of sites at once. Customers receive discounts and services that are not available on standard plans. o Concierge - Access to services and features not available on standard Squarespace plans, including SSO, custom billing, and volume discounts Average ACV: Tens of thousands of dollars 26#27INVESTOR DAY CASE STUDIES SQUARESPACE Industry: Healthcare Use Case: The company wanted a solution to help with scheduling appointments and testing for patients. They chose Squarespace due to our differentiated scheduling tools. November 2021 Industry: Real Estate Use Case: The company wanted to provide websites to its <2K real estate agents. They purchased a Volume plan with Squarespace because they were able to quickly integrate their technology with our platform to offer a scalable, fully customizable solution for every type of client. 27#28INVESTOR DAY LONG TERM ENTERPRISE GOALS SQUARESPACE 5%+ of Total Bookings from Enterprise Customers November 2021 28#29INVESTOR DAY SQUARESPACE CUSTOMER GROWTH AND ADOPTION November 2021 29#30INVESTOR DAY UNIQUE SUBS & ARPUS ARPUS Unique Subs (M) SQUARESPACE $178 2.3M 2018 ACUITY (4/19) & UNFOLD (10/19) $181 3.0M 2019 $186 3.7M 2020 $188 3.5M Q3 20 TOCK (3/21) $198 4.0M Q3 21 • Unique Subscriptions & ARPUS should be viewed in tandem. • Certain growth levers will likely impact these two factors differently. • Recent shift in growth (2018-2020 vs. 2021) as cross-sell motion improves. • Acquisitions have supported these KPI's in different ways since 2019. November 2021 30#31INVESTOR DAY UNIQUE SUBSCRIPTIONS SQUARESPACE UNIQUE SUBSCRIPTIONS WEBSITE ATTACHED SUBSCRIPTIONS GOOGLE WORKSPACE SCHEDULING DOMAIN UNFOLD TOCK CAMPAIGN UNATTACHED UNIQUE SUBSCRIPTIONS MEMBER AREA STANDALONE SCHEDULING WEBSITE WEBSITE WEBSITE EACH A UNIQUE SUBSCRIPTION DOMAIN DOMAIN DOMAIN WEBSITE GOOGLE WORKSPACE CAMPAIGNS WEBSITE UNFOLD STANDALONE SCHEDULING CAMPAIGNS WEBSITE GOOGLE WORKSPACE SCHEDULING MEMBER AREA TOCK DOMAIN November 2021 31#32INVESTOR DAY PRODUCT SQUARESPACE November 2021 UPDATES 32#33INVESTOR DAY SQUARESPACE INNOVATION 2004 Squarespace Launched SQUARESPACE 2012 Released v6 Commerce (CMS) Offering 2013 Released v7 w/ GSuite Integration 2014 2015 2016 Euro Availability First Non- English Language 2017 Formed Circle Community Partnered with Tucows (Domains Reseller) 2018 Campaigns (Email Mkting) Mobile App Launches 2019 Released v7.1 (CMS) Extensions Marketplace Volume & Concierge (Enterprise) 2020 SQSP Registrar Acquired Unfold (Social Presence) Acquired Acuity (Scheduling) Acquired Videolicious (Video) Member Areas Unfold BioSites & Studio 2021 SQSP Video Studio Acquired Tock (Hospitality)#34INVESTOR DAY CMS SQUARESPACE November 2021 34#35INVESTOR DAY CMS STRATEGY U SQUARESPACE EASE-OF-USE Styles in Editor New Page Interactions New Block Editors Asset Picker Universal Uploader Direct Button Editing Undo/Redo Auto Layout Fluid Engine TAM EXPRESSIBILITY Image Masks Generative Backgrounds Header Effects Button Styles Accordion Block Anchor Links Marquees Section End Caps Overlapping Images November 2021 35#36INVESTOR DAY A CONVERSATION WITH KATIE FLYNN A CONVERSATION WITH KATIE FLYNN A CONVERSATION WITH KATIE FLYNN (Gradients) (Shapes and Patterns) (Contours) A CONVERSATION WITH KATIE FLYNN A CONVERSATION WITH KATIE FLYNN BACKGROUND ART SQUARESPACE A CONVERSATION WITH KATIE FLYNN (User uploaded images) (Multi colors) (Noise and blur effects) (Repeating images) UQUDSLA Glaze Cream For 16 be tored PERFORMANCE BENDER Liquid Silk Cream Brightening Facial Cream ay of how can be made Machine of the 501 Glaze v2.0 Cream Perfect Balancing Essence Cream (Carousel) (Banner Slideshow) levels Simply load sequence by entering notes onder along with red and P 28 bevors AUTO LAYOUT (Great for lists of content with the same structure) (Multiple-columns) DUAL LEVEREQUENCE Cleansing Cream (One-click to change layout types) Shop About B FLOWERS FLOWERS HEADERS (Frosted blur) (Gradient fade) (Glows) (Borders) (Drop shadows) FLOWERS (Transparency range) (Add'l spacing options) Try free Discover the new products you'll love now and forever Discover the new products you'll love now and forever MASKS November 2021 Discover the new products you'll love now and forever (Border radius control) (Rounded corners) (Sharp edges) (Adjustable aspect ratios) (Waves and bulges) (Warps and arcs) (Ovals and ellipses) 36#37INVESTOR DAY USAGE INSIGHTS INFORMS ROADMAP SQUARESPACE DAILY AVERAGE 400k BLOCKS PER DAY ( Spacer Newsletter Quote Embed </> Code Y Menu Social Links Powered by Tock Reservations Business Product Member Sign Up Integrations Instagram a Amazon .. Flickr 5500px T D Audio Line Map Markdown Summary Calendar . Chart Events Donation Scheduling Twitter Zola Soundcloud RSS November 2021 37#38INVESTOR DAY VIDEO SQUARESPACE STUDIO November 2021 38#39INVESTOR DAY PREMIUM VIDEO TEMPLATES Promote your business with video templates from our award-winning Creative team. Add your logo and stand out with custom fonts, colors, voiceovers & music. SQUARESPACE 5:237 < BACK DURATION 19 sec DURATION 21 sec Select a Template LANDSCAPE ✓ EFFORT 20 min to shoot & edit . - ا... Voice Only Templates These templates only use audio narration, so you don't have to appear on camera. EFFORT 25 min to shoot & edit SELECT SELECT On-Camera Templates These templates have steps where you'll appear on camera. While it's more effort than voice only, it can help your video feel more personable and engaging. November 2021 39#40INVESTOR DAY INSTANT VIDEO ADS Create promotional videos in seconds - Autofill makes instant video ads from your site and store. We'll even create new promotional videos when you add new products. SQUARESPACE 5:26 BACK Classic Aviators AUTOFILL COMPLETE 2 ill? 3 November 2021 40#41INVESTOR DAY SMART VOICEOVERS Just type a script and we'll make an instant voiceover. Choose from multiple professional voices included with all Autofill templates. SQUARESPACE 12:22 al BACK Audio Narration Hi, my name is Rose Walker. I'm a financial advisor at Austin ... Vanessa EDIT MUTE USE SMART VOICE USE YOUR VO November 2021 41#42INVESTOR DAY SHARE ANYWHERE Share to social channels with just a few taps. Promotional videos are automatically resized to multiple aspect ratios for key social platforms like Facebook and Instagram. SQUARESPACE 5:25 < BACK 22-7 DURATION 31 sec T-18 DURATION 58 sec T-14 Select a Template LANDSCAPE ✓ EFFORT 20 min t Landscape Select an Orientation Portrait Square . - ا... TED SABGA SUIT TAILORS EFFORT 30 min to shoot & edit F [] SELECT November 2021 42#43INVESTOR DAY EARLY CUSTOMER FEEDBACK 4.9 179 Ratings "Oh wow, @squarespace... you've outdone yourself! Loving the video studio app. I'm literally able to create a clean, quality video in less than 15 minutes!" "It's amazing. Leaving aside what this app does (which is very original), I'm in awe of the way that it does it. This sets the bar for what new releases should look like." SQUARESPACE "Thank you for this fantastic app. As a small business this is a game changer!!!" "Really wonderful design and love how you can plug in videos and voice overs!" November 2021 "This is an amazing asset to Squarespace!" 43#44INVESTOR DAY CUSTOMER TESTIMONIALS SQUARESPACE "Squarespace Video Studio has positively impacted my business with an increase in traffic as well as subscriptions to my blog and shop updates. Once I posted the video I created on social media, I saw an increase in traffic and engagement to my website." HEY ALISHA SQUARESPACE CUSTOMER November 2021 44#45INVESTOR DAY ONLINE SQUARESPACE STORES November 2021 45#46INVESTOR DAY ONLINE STORES Key Features Easy, guided setup for DIY Entrepreneurs Product catalog management Product merchandising and sales tools Mobile-optimized checkout Order management and fulfillment Advanced tools & integrations for shipping and taxes SQUARESPACE Crosby Sales Overview Revenue $5,479 Units Sold 94 Orders 105 Shop Our Story Blog Contact Plants and Pots For Your Home Shop Now November 2021 Crosby Plants and Pots For Your Home Shop Now 46#47INVESTOR DAY DIFFERENTIATORS Branded Store Out-of-the-Box Best-in-Class DIY Built-in Features Integrated with Squarespace Platform SQUARESPACE Mish-Mash $40 Happy Stack Add to Bag BAAN BOON Welcome Our Home To Yours! नि corner - quarter afterpay Shop now. Pay later. Always interest-free. B Set w fe Ps 1 New November 2021 Iv 40 493 47#48INVESTOR DAY MEET LAURA LOMBARDI Jewelry Designer based in NYC SQUARESPACE All Earrings Necklaces Bracelets Rings Accessories Silver Theme Gift Guide NOW OFFERING INTERNATIONAL SHIPPING WITH DHL | FREE SHIPPING ON ORDERS OVER $100 (USA) LAURA LOMBARDI HOME ABOUT SHOP MOODBOARD COLLECTION Silver Treccia https://www.lauralombardi.com/shop/p/silver-treccia-necklace Necklace $164.00 Silver Piatta ممما لمما Silver Cusp Hoops $200.00 Silver Strada Q Search Silver Mini Omega Chain $168.00 Silver Noemi Dendent ?? November 2021 48#49INVESTOR DAY LATEST UPDATES Key Features for Marketplace Sellers Launched in Q3 O Import Etsy products & reviews New seller guidance 00 O Local Pickup Coming in Q4 Shipping labels Native Product reviews O O SQUARESPACE FI Q Pamer Mac Ow Golden M Ge Courey From Se Etsy Import Login to import all y products to your After the products are imported, you can et the product name, price, quencty description and more QERALL $35.00 239.00 12.00 2. Order Options Shipping Pickup Options • Upper West Shop Lower East Side Shop Pickup Information 8 Clarkson Street 10th Floor New York, NY 10014 Monday 10:00am - 6:00pm Tuesday 10:00am - 6:00pm Wednesday 10:00am - 6:00pm Thursday 10:00am - 6:00pm Friday 10:00am - 6:00pm November 2021 Continue Pickup Saturday Closed Sunday Closed Please show a form of ID when picking up your order. 49#50INVESTOR DAY MEMBER SQUARESPACE AREAS November 2021 50#51INVESTOR DAY Rise in the Creator Economy SQUARESPACE Subscription memberships have risen in popularity Trends are here to stay post-pandemic November 2021 51#52INVESTOR DAY MEMBER AREAS Engage your audience with exclusive content SQUARESPACE PASSERO COOKING SCHOOL Gain access to unlimited cooking classes for $15/month. Video Instruction Exclusive Recipes ABOUT CLASSES CONTACT Recommended tools LOGIN November 2021 H 52#53INVESTOR DAY USE CASES CLASSES/COURSES Yoga instructor selling access to yoga videos SQUARESPACE 4524 COMMUNITY Private Leadership community for women || . . ||||||| INGRESOS ESTADOS GRAFICAS November 2021 PREMIUM CONTENT Traders offering exclusive content and expertise 53#54INVESTOR DAY NICOLE FIORE SQUARESPACE 7. November 2021 https://thatnicolefiore.com/ 54#55INVESTOR DAY RECENT UPDATES Multiple Fee Options Onboarding Tools Restricted Membership Feature SQUARESPACE November 2021 55#56INVESTOR DAY SCHEDULING SQUARESPACE November 2021 56#57INVESTOR DAY SCHEDULING Mission We help businesses who rely on appointments do more of what they enjoy. SQUARESPACE ~80% Q3 2021 GMV Y/Y Growth November 2021 >60% Q3 2021 Y/Y Rev. Growth 57#58INVESTOR DAY SQUARESPACE SCHEDULING FEATURES Our feature set saves businesses time and provides their clients with a fast and seamless booking experience: SQUARESPACE Offerings • Appointments or Classes • Sell packages and subscriptions • Upsell clients with Add-Ons • Virtual appointments with Google Meets, Zoom, or GoToMeeting Native Client mobile app to view and book appointments Customize • Design Scheduling Page • Confirmation, reminder, follow up emails • Customize SMS message reminders ● Embed booking flow on website • Appt. intake form questions • Multiple time zones & languages Scale • Multiple staff members • Advanced reporting November 2021 • Sync with personal calendars • Manage appointments on mobile app Client member accounts • 3rd party integrations Payments • Accept payments with Stripe, Square, or PayPal • Accept deposits or tips • Create coupons or discounts • Vault client credit cards • Connect accounting integrations 58#59INVESTOR DAY ...FOR BUSINESSES OF ALL SIZES STARTING OUT 1 Team Member 1 Location & time zone 3 Appointment Types Accepts Payments SQUARESPACE GROWING 3 Team Members 1 Location & time zone 10 Appointment Types Accepts Payments Offers Add-Ons Automated follow up emails SCALE 15 Team Members 3 Locations & times zones 15 Appointment Types 5 Classes November 2021 Accepts Payments Offers Add-Ons, Packages & Subscriptions Automated follow up emails SMS appointment reminders Intake forms & client note taking Integration with accounting software 59#60INVESTOR DAY CUSTOMER TESTIMONIALS SQUARESPACE "The use of Scheduling has improved our business in ways words can't explain. Our creative studio has a very high volume of clients-averaging over 400 scheduled appointments per month. With Scheduling on our website, we're able to conveniently meet their needs in a timely manner." CAM KIRK STUDIOS SQUARESPACE CUSTOMER November 2021 60#61INVESTOR DAY THE FUTURE OF SCHEDULING BEST IN CLASS Give small and medium sized businesses that rely on scheduling the tools they need to grow their volume (incl. group & series classes) SQUARESPACE ALL-IN-ONE Further integration with Squarespace (i.e. CMS, Campaigns, etc.) to create visible pathways that will result in increased awareness, adoption and cross-sell WORKFLOW SOLUTIONS November 2021 Enable scheduling as an integral part of the overall digital workflow to manage a business online 61#62INVESTOR DAY SQUARESPACE TOCK November 2021 62#63INVESTOR DAY SQUARESPACE tock SQUARESPACE SELL ANYTHING > RESTAURANTS & HOSPITALITY Tock is the all-in-one reservation system PRODUCTS ✓ Seamlessly manage réservations, events, takeout, and delivery all in one place, with the power of Tock. START WITH TOCK Need a website? START WITH SQUARESPACE → TEMPLATES RESOURCES ✓ Reservations Events November 2021 LOG IN 63#64INVESTOR DAY TOCK DASHBOARD OFFER Ordinary Free Reservations Deposit Reservations Fully Prepaid Bookings SQUARESPACE FOR A La Carte Dining Chef's Tables Private Events Tasting Menus Wine Pairings Tours Cookbooks Charitable Donations Snapshot of Oct 12 E 162 Guests Brunch, Dinner 81 Booked 9 Held 40 Walk-in 32 Available November 2021 64#65INVESTOR DAY EXPLORETOCK AS OF 09/30/21 21M Guest Accounts AS OF 09/30/21 70% Mobile SQUARESPACE AS OF 09/30/21 26/200 Cities Countries AS OF 09/30/21 49% Guests 34 y/o and under Otock Q Search Your destination for all things delicious. Reservation type Dine-In Dine-In Location Nashville, TN Pickup & Delivery tock 1 Napa Valley, CA Somerston Estate 0.7 miles $$$-Winery Explore all that Tock has to offer. Book for Nov 16-17 Q Search Events Somerston Estate Tour & Tasting Thanksgiving Paraduxx Winery It's time to feast. Explore traditional dinne 6.5 miles $$$ Winery Prepaid reservation for parties of 1 to 4 $100 per person Book for Nov 11-17 Nov 10-17 2 guests Date Wed, Nov 10 Paraduxx Tasting Experience Prepaid reservation for parties of 1 to 6 $50 per person Robert Sinskey Vineyards 6.6 miles $$ Winery Time Now Wineries Produce All experiences Kellogo Party size. 2 guests 20 Arts & Culture 9 R OD 09 Q PPPP Ⓡ. Lek Farvila 9 a&a 90 9 90 November 2021 65#66INVESTOR DAY INTEGRATIONS TOCK BLOCK Quote </> Code Embed Y Menu Powered by Tock Reservations G Social Links Business SQUARESPACE Product Integrations Member Sign Up Instagram Amazon Flickr 500px Map Markdown Summary Calendar . Chart Events O Donation Scheduling Twitter Zola Soundcloud RSS Reservations Join Tock The All-in-one reservation system. Tock allows you to manage reservations, events, tableside payments, deposits, takeout and more. LEARN MORE ALREADY A CUSTOMER Events Join Tock Sell out your next event with Tock's premier hospitality event and ticketing platform, packed with all the tools you need to successfully run and manage events of any size. CREATE YOUR FIRST EVENT November 2021 ALREADY A CUSTOMER 66#67INVESTOR DAY WHAT'S NEXT... RETAIL MARKETPLACE & TOCK TIME SQUARESPACE tock The 2021 Tock Wine Holiday Collection 171 HAN Jazeer "ITY). November 2021 67#68INVESTOR DAY SQUARESPACE UNFOLD Alfonso Cobo Head of Unfold O Send Message NEW Effects NEW UHS Sparkle NEW NEW ASTRO NEW O Send Message Glitch 4:39 1 FREE with UNFOLD+ 12:22 1 ovember 2021 Colors 5GE + Brand Kit PRO x #CCE187 Logos 68 + #EER Ur Fa#69INVESTOR DAY Un SQUARESPACE BEBRENECERGE84888888 НЕЕ 1666СЕТЕСЕСВЕННОЕ HHA сенсен 88 ARE nini Alfonso Cobo Founder & Creator ! November 2021#70INVESTOR DAY SQUARESPACE We enable Creators to stand out, grow and monetize on Social November 2021 70#71INVESTOR DAY $100B The Creator Economy SQUARESPACE Different tools aid creators in their day-to-day interaction with their audiences, helping foster relationships through different platforms. More than 50 million people around the world consider themselves creators, despite the creator economy only being born a decade ago. Source: Influencer Marketing Hub; Signal Fire November 2021 71#72INVESTOR DAY THE CREATOR SPACE IS FRACTURED. Currently, users must cobble together multiple tools to start and grow a social-first brand that spans multiple channels (e.g. Adobe Spark: content creation, Later: social scheduling, Linktree: Link in Bio solution). GoDaddy Studio SQUARESPACE Later UN UM linktree VSCO Sp Canva November 2021 72#73INVESTOR DAY U SQUARESPACE AND WE'VE BEEN EVOLVING... We are the all-in-one platform for the next generation of entrepeneurs who want to be successful on Social November 2021 73#74INVESTOR DAY SOLVING FOR SOCIAL SQUARESPACE STAND OUT. EVERYWHERE Social Templates that make it easy to create thumb-stopping, professional-level content with no skills, and Bio Sites to establish your Social presence. ALL-IN-ONE, FOR YOU BUILD YOUR AUDIENCE Integrated Tools and guidance to help you grow your audience and establish a direct relationship with your customers SELL ANYTHING A diverse set of audience monetization Tools, such as tipping or paywalled content. November 2021 Solving the same problem as Squarespace, but for Social First customers 74#75INVESTOR DAY FINDING BALANCE I find myself in a creative block I always ing to light my candles. VLAANDUIT JE NEW FUNARI TUVIE EST-2018 CREATED WITH Clasico Ol CREATE SHARE SQUARESPACE THE TOOLKIT FOR STORYTELLERS FROM SQSP THE FUTURE BELONGS TO THE STORYTELLER 8 CLARKSON ST NEW YORK-NY 10012 EST-2018 November 2021 75#76INVESTOR DAY CONTENT CREATION SQUARESPACE 12:22 1 Discover Q Search Clasico For You Trending Endless Adventive Templates Film Studio Hierve el Agus al 。 00 00 Plan TRY PLUS My Projects Scrapbook SEE ALL Plas SEE ALL + Bio Site 12:22 1 ← Story Name THE SUMMER OF Endless Adventure + REYKIR 44 BEDFORD VHS November 2021 BRIGHTON 76#77INVESTOR DAY CONTENT MANAGEMENT SQUARESPACE 12:22 1 = Anne v Tabant 6 Templates MUS ADD TO GRID Studio 8.9 Plan M O Bio Site 31 Scheduled posts 08/10/2021 5:00pm 09/01/2021 9:00am 10/10/2021 9:00am CLOSE Cancel August 2021 > 1 Date Tuesday, August 10, 2021 SUN MON TUE WED THU 2 3 4 Schedule O 5 29 30 31 < Time 12:00 FRI Add > 8 9 10 11 12 13 14 SAT 15 16 17 18 19 20 21 6 7 22 23 24 25 26 27 28 November 2021 77#78INVESTOR DAY BIO SITES SQUARESPACE bio.site/ellasimmons Ella Simmons PHOTOGRAPHER Of 4 My Most Recent Projects My Portfolio Watch My Latest Video Sign My Petition Visit My Online Store November 2021 78#79INVESTOR DAY MONETIZATION SQUARESPACE 12:22 1 Bio Site Activity BASED IN LOS ANGELES CA TITLE GOES HERE Templates bio.site/anne QUINN STUDIOS @fy JO TITLE GOES HERE TITLE GOES HERE TITLE GOES HERE Studio Payments Planner 01 02 03 04 Bio Site 12:22 1 = Bio Site All 1D Views All Time 100% ↑ Clicks All Time 100% ↑ CTR All Time 100% ↑ Tips All Time 100% ↑ Templates 6 8 Activity Studio 7D Planner Payments 30D 9.2K 674 12% 112 O Bio Site 12:22 1 = Bio Site Activity TOTAL EARNINGS (10) $136.00 Support Me Aug 2, 2021 # 3212321 Gavin Thompson View email Support Me Aug 1, 2021 # 3212977 Bea Metitiri View email Support Me Jul 27, 2021 # 3212654 John Garrahan View email Michael Elias Templates Studio Planner Payments |~ November 2021 $16.00 $17.00 $6.00 $8.76 Bio Site 79#80INVESTOR DAY ADDRESSABLE MARKET SQUARESPACE SMALL BUSINESS CREATORS/ SOLOPRENEURS CONSUMERS November 2021 All-in-one professional tool No outsourcing or skills needed, affordable, reflective of evolving social trends Ease of use, Mobile-first, start for free 80#81INVESTOR DAY SOCIAL MEDIA SOLUTIONS (COMPETITIVE LANDSCAPE) Social media templates Photo/Video filters & effects Content planning (feed, scheduling, captions) Link in Bio solution Social Monetization capabilities SQUARESPACE >>> GoDaddy Studio Later UN UM linktree VSCO November 2021 Sp ← 81#82INVESTOR DAY PERSONAS Unfold will make way for the next generation of entrepreneurs to build and grow online by establishing their voices and monetizing their ideas in new ways SQUARESPACE CREATORS/SOLOPRENEURS Pisco Morgan Fashion Influencer I'm a one-person show trying to stand out in a crowded industry. Uses Unfold for Driving my growing audience to top links with Bio Sites: custom presets, brand collaborations, promo codes, social pages, and payment handles Quickly creating trendy, engaging social content that matches my aesthetic with templates Managing my social media on the go, from my phone, in minutes November 2021 SMALL BUSINESS Rebekah Friedman Innri, a Health & Wellness brand Managing my different ventures and audiences is a challenge. Uses Unfold for Create engaging, unique social content with templates, and apply brand styles across social presence to legitimize my business Manage and schedule social media posts in advance to save time Direct traffic to website, YouTube series, meditation podcast, newsletter, and coaching sessions with Bio Sites 82 82#83INVESTOR DAY 50M DOWNLOADS SQUARESPACE UNFOLD 6084 FF1 UNFOLD 6006 FF1 November 2021 1.4B STORIES 83#84INVESTOR DAY SUBSCRIPTIONS I SQUARESPACE Current Offering November 2021 o Unfold+ - Launched in 2019. - Geared towards Creators who want to stand out on Social. Includes access to all of our design tools. o Unfold Pro - Launched in 2020. The perfect plan for SMBs. Includes access to services and features not available on standard the Unfold+ plan, including Brand Kit, managing multiple Instagram accounts, Scheduling, Web Stories and the Web Dashboard. 84#85INVESTOR DAY Top 10 Graphics & Design app in 98 countries SQUARESPACE 0 November 2021 85#86INVESTOR DAY SQUARESPACE INFLUENCING CULTURE Southern Province, Sri Lanka Sigiriya November 2021 The biggest celebrities, brands and influencers worldwide use Unfold to share their content online 86#87INVESTOR DAY Best of the Year Best Apps - Apple SQUARESPACE 2019 Best of the Year Best Apps - Google 2018 November 2021 Design Awards Innovation by Design - Fast Company 2019 87#88INVESTOR DAY OUR JOURNEY PRODUCT RELEASES Collection Fonts 2017 SQUARESPACE PRODUCT RELEASES Additional collections Collection store Unfold for Enterprise MILESTONES Equinox Partnership Product(RED) Partnership 2018 1 PRODUCT RELEASES New Text tools MILESTONES Acquired Stylecolor & Carve Tommy Hilfiger Partnership Google App of the Year Join SQSP 2019 UNFOLDE PITCH PRODUCT RELEASES Unfold Pro SQSP accounts Brand Kit Web Stories Filters & Effects Post Templates MILESTONES Apple's Trend of the Year 2020 Jewelry-by Anise PRODUCT RELEASES Animated Templates Instagram Feed Planner Post Scheduling Bio Sites Monetization Capabilities MILESTONES 1B Stories Created 50M Downloads November 2021 2021 88 20#89INVESTOR DAY UNFOLD x SQUARESPACE We are uniquely positioned to capture the Creator Economy We have a prime opportunity to reach nascent businesses starting on social, as well as help our website customers grow their audience through our tools. Your Brand, everywhere Squarespace accounts make it easier than ever to share a beautiful, consistent brand vision across platforms. Nurturing the next generation of Entrepreneurs We will win by being the platform of choice for Gen Z who want to be successful on Social by making it easy for them to stand out, grow and monetize their audiences. SQUARESPACE Maca We think you'll like these cult favorites. Continue building your skincare routine with our bestselling products. With pH balancing formulas and non-toxic ingredients, upgrading your regimen has never been this gentle on your skin. Shop Best Sellers Style Background Color Email Color FONT Font Pack Font Sizes Email Styles Link Color Email AUTOFILL SITE STYL November 2021 Maca Maca NUTRIENT-RICH FORMULAS FOR EVERY SKIN TYPE My Site Blog Shop Gifts UNFOLD 89#90INVESTOR DAY SQUARESPACE The Future November 2021 90#91INVESTOR DAY UNFOLD 8.0 SQUARESPACE 12:22 1 || For You Stories Posts USE TEMPLATE Recommended Stories X Home Projects + Q + Video Plan Stud SEE ALL O Bio Site 12:22 1 ← Project Name O Background Add Text Stickers OÛ Slideshow + = Bio Site Home Activity YOGA AND WELLNESS STUDIO 8 ALIGN & FLOW JOIN MY NEXT RETREAT SHOP QUINN X FLOW bio.site/anne edited 5/14/2021 Projects Wallet + 00 00 Plan 01 Audience 02 : November 2021 Bio Site Let ZA Wat bic 91#92INVESTOR DAY Content Creation Video SQUARESPACE 0.0 +2.5 5.0 DUOTONE 7.5 Sparkle November 2021 92#93INVESTOR DAY Content Management Cross-platforms SQUARESPACE Shorts Year In Review 21.1K views Upstate 21.1K views 23 J BAY ⠀ O November 2021 93#94INVESTOR DAY Bio Sites New Audience Monetization Tools SQUARESPACE 124 Private Meditation Fitness Blender Provides Free Full Length Workout Videos, Workout Routines, Equity & Excellence for All DONORS UNLOCK FOR ($200) $16,400 $50K RAISED GOAL GIVE DONATION 70% Q Request a custom Happy Birthday Song SEND REQUEST November 2021 LIGHTROOM PRESET The feel of real film is here for you. This bundle contains vintage presets to make your photos look more authentic DOWNLOAD $12 94#95INVESTOR DAY Bio Sites NFTS: Take control and ownership over your Creative Platform SQUARESPACE COLETTE NOLL NFT Gated Bio Site This Bio Site is exclusive to holders of PLEXUS. Connect your wallet to unlock. A Connect Wallet to Unlock LEARN MORE > Ocean $1500.00 The Colour of Code is a collaborative project that shall explore different themes of art, data structures, loops, recursions and object oriented programming. MAKE AN OFFER File Name Storm November 2021 Create New Item Blockchain Etherium. REMOVE 95#96INVESTOR DAY Bio Sites Engage your Audience SQUARESPACE Stay in touch For Exclusive recips, discounts, opportunities and new product announcements - plus a few surprises. Enter your email JOIN Monday, January 21 6:00am 8:00am 10:00am 7:00am 9:00am 11:00am Who should I interview first? 01 02/ 03/ 04/ Jay Montclaire Mark Novo Sebastian Toledo Helen Gates ALL THINGS WOMEN'S WELLNESS BOOK AN APPOINTMENT 60 minutes @ $10.00 BOOK November 2021 96#97INVESTOR DAY Bio Sites Boundary-Pushing Designs SQUARESPACE 3D Motion SIMONE&CO BLOG MY YOUTUBE ACAPELLA SINGER O ♥NEW VIDEO OUT NOW! November 2021 ل و Timeshifting Designs 01 02 03 97#98INVESTOR DAY Upselling Unfold customers to SQSP services If you've gotten traction on Bio Sites and want to grow your brand/business, you'll likely want to be monetizing on both Unfold & Squarespace. This might include services such as Scheduling, Domains or Email Campaigns. SQUARESPACE 12:22 1 = vity S 27 9AM 10AM 11AM 12PM 1PM 2PM 3PM Payments M 28 T 0 Templates 29 Mailing List JOE Oprah Winfrey Ice Walking 2:00pm-3:30pm W Studio T Wednesday October 30, 2019 30 31 al? Schedulin F 88 Planner 01 Scheduling MARIA Oprah Winfrey Ice Walking 9:00am-10:30am Oprah Winfrey Glacier Surfing 11:00am-12:00pm Oprah Winfrey Glacier Surfing 11:00am-12:00pm 02 Oprah Winfrey Glacier Surfing 11:00am-12:00pm S Class: Glacier Surfi Bio Site 12:22 1 Type to search ? 123 Claim your domain. qw e r a S ALREADY HAVE A DOMAIN? Transfer your domain in just a few easy steps. N d u ty i fghjk X C al space @ V bn m Domains O I return р Payments TAL SUBSCRIBERS 2 042 @apple.com Tim Cook [email protected] Catherine Adams @microsoft.com Anika Anderson @gmail.com Evan Cue Mailing List [email protected] Craig Federighi D lates 10 November 2021 SEND EMAIL CAMPAIGN Studio Planner Scheduling Campaigns O Bio Site 98#99INVESTOR DAY FINANCIALS C -TO 00 SQUARESPACE FY 2019 & FY 2020 financial information is based on audited financial statements; FY 2018 and prior and all quarterly financial information is based on unaudited financial statements. Please see the Appendix at the end of this presentation for reconciliations of non-GAAP metrics to the nearest GAAP equivalent. November 2021 99#100INVESTOR DAY Predictable & Transparent >90% Subscriptions via Annual & Monthly Plans SQUARESPACE + BUSINESS MODEL Recurring & Upside Revenue SaaS + Volume Based Payments + Highly Efficient Model High Gross Profit Margins Enables Expansion at Minimal Incremental Costs FEST + November 2021 Strong Operating Leverage Attractive Cash Flow Margins 100#101INVESTOR DAY REVENUE GROWTH (IN MILLIONS) SQUARESPACE $800 $600 $400 $200 $0 26% 2-Yr CAGR $390M $47M $343M 2018 $485M $81M $404M 2019 Commerce $621M $143M $478M 2020 Presence 28.5% YoY $449M $99M $350M 9M 20 $577M $165M $411M 9M 21 November 2021 101#102INVESTOR DAY REVENUE BREAKDOWN (YTD Sept' 21) SQUARESPACE • Non-Subscription Commerce Based (7%) • Subscription Based (92%) • Non-Subscription Presence Based (<1%) 92% • GMV-Related Rev. Share w/ 3rd Parties Basic & Advanced Commerce Plans • Scheduling Member Areas • Campaigns • Hospitality Personal & Business Website Plans • Domains Google Workspace (Net) • Social Enterprise November 2021 Rev. Share w/ 3rd Parties (i.e. Getty) Social 1x Purchases Commerce Revenue (~29% of Total) o 2020 $143M; 78% YoY O YTD Q3 2021: $165M; 67% YoY ● Presence Revenue (~71% of Total) o 2020 $478M; 18% YoY o YTD Q3 2021: $411M, 18% YoY 102#103INVESTOR DAY SQUARESPACE LONG-TERM TARGETS November 2021 103#104INVESTOR DAY COMMERCE LONG TERM TARGETS SQUARESPACE Commerce Driving >50% of Total Revenue November 2021 104#105INVESTOR DAY INTERNATIONAL LONG TERM TARGETS SQUARESPACE November 2021 International Driving >50% of New Website Subscriptions 105#106INVESTOR DAY CIRCLE LONG TERM TARGETS SQUARESPACE Double (2x) Active Circle Members to ~50K November 2021 106#107INVESTOR DAY ENTERPRISE LONG TERM TARGETS SQUARESPACE Enterprise will represent 5%+ of Total Bookings November 2021 107#108INVESTOR DAY SQUARESPACE LONG-TERM MARGINS November 2021 108#109INVESTOR DAY Non-GAAP GROSS MARGINS SQUARESPACE 84% 85% 85% 11 || 2018 2019 86% 2020 9M21 Please see the Appendix at the end of this presentation for reconciliations of non-GAAP metrics to the nearest GAAP equivalent. Around 80% November 2021 Long-Term Gross Margin Target 109#110INVESTOR DAY Non-GAAP R&D (IN MILLIONS) SQUARESPACE 18% $69M 2018 19% $92M 2019 23% $142M 2020 20% $113M 9M21 Please see the Appendix at the end of this presentation for reconciliations of non-GAAP metrics to the nearest GAAP equivalent. Mid 20%s Long-Term R&D Expense Ratio November 2021 110#111INVESTOR DAY Non-GAAP M&S (IN MILLIONS) SQUARESPACE 38% $147M 2018 37% $181M 2019 41% $253M 2020 41% $235M 9M 2021 Please see the Appendix at the end of this presentation for reconciliations of non-GAAP metrics to the nearest GAAP equivalent. High 30%'s Long-Term M&S Expense Ratio November 2021#112INVESTOR DAY Non-GAAP G&A (IN MILLIONS) SQUARESPACE 9% $36M 2018 9% $42M 2019 7% $45M 2020 9% $53M 9M21 9M21 non-GAAP G&A expense excludes $25.3 million in Direct Listing fees. Please see the Appendix at the end of this presentation for reconciliations of non-GAAP metrics to the nearest GAAP equivalent. <10% Long-Term G&A Expense Ratio November 2021 112#113INVESTOR DAY uFCF SQUARESPACE uFCF Margin uFCF (M) 21% $83M 2018 20% $95M 2019 25% $152M 2020 19% $109M 9M 21 In the 20%'s Long-Term uFCF Margin November 2021 113#114INVESTOR DAY LONG TERM FINANCIAL TARGETS (Non-GAAP) % of Revenue Gross Margin R&D M&S G&A uFCF Margin SQUARESPACE 2020 86% 23% 41% 7% 25% 9M21 85% 20% 41% 9% 19% Please see the Appendix at the end of this presentation for reconciliations of non-GAAP metrics to the nearest GAAP equivalent. LT TARGET ~80%'s November 2021 Mid-20%'s High 30%'s <10% 20%'s 114#115INVESTOR DAY SQUARESPACE APPENDIX November 2021 115 5#116INVESTOR 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%#117INVESTOR DAY GAAP VS. NON-GAAP RECONCILIATION (IN THOUSANDS) Net Income/(Loss) Add-back: Interest Add-back: Provision for Income Taxes Add-back: Amortization and Depreciation Add-back: Stock-Based Compensation Add-back: Other Income Add-back: Special Bonus Add-back: Direct Listing Costs Adjusted EBITDA Margin Cash from Operating Activities Capex Free cash flow Cash net of interest Unlevered free cash flow Margin SQUARESPACE Q1 2018 $1,740 73 288 2,687 1,236 523 0 0 $6,547 7% $44,617 -8,352 36.265 60 $36,325 40% Q2 2018 Q3 2018 $21,371 55 6,708 2,853 1,429 (1,310) 0 0 $31,106 32% $16,272 -5,078 11,193 47 $11,240 12% $18,451 33 5.502 3,222 2,404 (352) 0 0 $29,260 29% $30,716 -8,489 22,227 30 $22,257 22% Q4 2018 $1,561 12 1.594 3,969 1,949 (1,493) 0 0 $7,592 7% $20,313 -7,244 13,070 13 $13,083 12% Q1 2019 $5,153 1 1,668 3,665 2,510 (1,294) 0 0 $11,703 11% $45,101 -2,218 42,883 2 $42,886 39% Q2 2019 $21,310 118 7,107 4,387 4,243 (47) 0 0 $37,118 32% $30,098 -528 29,570 0 $29,570 25% Q3 2019 $18,406 157 6,919 4,701 5,212 (4,931) 0 0 $30,464 24% $33,065 -4,241 28,824 0 $28,824 23% All quarterly data unaudited. Amounts may not sum due to rounding. Q4 2019 $13,283 804 (9,771) 5,556 6,010 2,457 0 0 $18,339 14% ($5,931) -1,230 -7,162 453 -$6,709 -5% Q1 2020 ($10,132) 3,130 (4,142) 5,637 7,902 (1,205) 0 0 $1,190 1% $52,469 -1.274 51,195 2,169 $53,364 39% Q2 2020 $18,539 2,456 4,372 5,551 7,268 1,319 0 0 $39,505 26% $46,445 -944 45,501 1,769 $47,270 32% Q3 2020 $17,924 2,460 3.917 5,171 7,653 3,488 0 0 $40,613 25% $44,853 -1,420 43,433 1,761 $45,194 28% Q4 2020 $4,257 1,997 (12,236) 5,344 8,431 4,076 23,489 $35,358 21% $6,263 -1,074 5,189 1,422 $6,611 4% Q1 2021 ($1,146) 3,260 (5,782) 8,506 9,852 (3,593) 0 0 $11,097 6% $50,131 -657 49,474 2,308 $51,782 29% Q2 2021 ($234,532) 2,827 (10,413) 7,726 250,513 1,201 0 25,318 $42,640 22% $8,692 -1,758 6,934 3,320 $10,254 5% Q3 2021 $2,839 2,491 3,756 7,674 23,734 (2,101) 0 0 $38,393 19% $49,344 -4,329 45,015 2,236 $47,251 24% 2018 $43,123 173 14,092 12,732 7,019 (2,633) 0 0 $74,506 19% $111,917 (29,163) 82,754 150 $82,904 21% 2019 $58,151 1,080 5.922 18,309 17,975 (3,815) 0 0 $97,623 20% November 2021 $102,334 (8,218) 94,116 455 $94,571 20% 2020 $30,588 ($232,839) 10,043 8,578 (8,089) 21,703 31,254 7,678 23,489 0 $116,666 19% YTD 2021 $150,030 (4,712) 145,318 7,121 $152,439 25% (12,439) 23,906 284,099 (4,493) 0 25,318 $92,130 16% $108,167 (6,744) 101,423 7,864 $109,287 19% 117#118INVESTOR DAY GAAP VS. NON-GAAP RECONCILIATION (IN MILLIONS) (in millions) Cost of Revenue less: Stock-based Compensation less: Depreciation & Amortization Non-GAAP Cost of Revenue Marketing and Sales less: Stock-based Compensation Less: Depreciation & Amortization Non-GAAP Marketing & Sales Research and Development less: Stock-based Compensation less: Depreciation & Amortization Non-GAAP Research and Development General and Administrative less: Stock-based Compensation less: Depreciation & Amortization less: One time direct listing costs Non-GAAP General and Administrative SQUARESPACE FY 18 $70.2 $0.3 $7.1 $62.8 $149.0 $0.7 $0.9 $147.4 $75.9 $4.1 $2.9 $69.0 2018 and YTD 2021 (as of Q3) data unaudited. Amounts may not sum due to rounding. $40.0 $1.9 $1.9 $0.0 $36.2 FY 19 $81.9 $0.5 $9.6 $71.8 $184.3 $1.7 $1.2 $181.3 $107.6 $12.1 $3.8 $91.7 $49.6 $3.6 $3.6 $0.0 $42.3 FY 20 $98.3 $0.8 $10.2 $87.4 $260.0 $3.1 $3.6 $253.3 $167.9 $21.6 $4.0 $142.3 November 2021 $54.6 $5.7 $3.8 $0.0 $45.1 YTD Q3 2021 $92.8 $1.1 $7.6 $84.1 $249.0 $4.5 $10.0 $234.6 $139.7 $23.8 $3.0 $112.9 $336.3 $254.7 $3.4 $25.3 $52.9 118#119INVESTOR DAY November 2021 DEFINITIONS Unique subscriptions represent the number of unique sites, standalone scheduling subscriptions and Unfold (social) subscriptions, as of the end of a period. A unique site represents a single subscription and/or group of related subscriptions, including a website subscription and/or a domain subscription, and other subscriptions related to a single website or domain. Every unique site contains at least one domain subscription or one website subscription. • Total bookings represents cash receipts for all subscriptions purchased, as well as payments due under the terms of contractual agreements for obligations to be fulfilled. • Annual run rate revenue ("ARRR") is calculated as the monthly revenue from subscription fees and revenue generated in conjunction with associated fees (fees taken or assessed in conjunction with commerce transactions) in the last month of the period multiplied by 12. • Average revenue per unique subscription ("ARPUS") is calculated as the total revenue during the preceding 12-month period divided by the average of the number of total unique subscriptions at the beginning and end of the period. • Gross merchandise volume ("GMV") represents the value of merchandise, physical goods, content and time sold, including hospitality services, net of refunds, on our platform over a given period of time. • Adjusted EBITDA is a non-GAAP financial measures. We calculate adjusted EBITDA as net income/(loss) excluding interest expense, other income/(loss), net, provision for/(benefit from) income taxes, depreciation and amortization, stock-based compensation expense and other items that we do not consider indicative of our ongoing operating performance. For a reconciliation of this non-GAAP financial measure to the most directly comparable financial measure calculated in accordance with GAAP, please see the reconciliations provided on the previous slides. • Unlevered free cash flow (UFCF) is a non-GAAP financial measures. We define unlevered free cash flow as cash flow from operating activities less cash paid for capital expenditures increased by cash paid for interest expense net of the associated tax benefit. For a reconciliation of this non-GAAP financial measure to the most directly comparable financial measure calculated in accordance with GAAP, please see the reconciliations provided on the previous slides. SQUARESPACE 119