#1◆Dropbox Company Presentation May 2022#2Safe Harbor Statement This presentation contains forward-looking statements. These statements may relate to, but are not limited to, plans for growth, technological capabilities and new features and products and the long-term financial targets of Dropbox, Inc. ("Dropbox," "we," "us," or similar terms), as well as assumptions relating to the foregoing. Forward-looking statements are inherently subject to risks and uncertainties, some of which cannot be predicted or quantified. In some cases, you can identify forward-looking statements by terminology such as "may," "will," "should," "could," "expect," "plan," anticipate," "believe," "estimate," "predict," "intend," "potential," "would," "continue," "ongoing" or the negative of these terms or other comparable terminology. You should not put undue reliance on any forward-looking statements. Forward-looking statements should not be read as a guarantee of future performance or results, and will not necessarily be accurate indications of the times at, or by, which such performance or results will be achieved, if at all. Forward-looking statements are based on information available at the time those statements are made or management's good-faith beliefs and assumptions as of that time with respect to future events, and are subject to risks and uncertainties that could cause actual performance or results to differ materially from those expressed in, or suggested by, the forward-looking statements. In light of these risks and uncertainties, the events and circumstances contemplated by the forward-looking statements made in this presentation may not occur and actual results could differ materially from those anticipated or implied in the forward- looking statements. These risks and uncertainties are described in greater detail under the heading "Risk Factors" in our annual report on Form 10-K for the fiscal year ended December 31, 2021 that we filed with the Securities and Exchange Commission (the "SEC") on February 18, 2022, and include, but are not limited to, the impact to our financial results, business operations, the business of our customers, suppliers, partners and the economy as a result of the COVID-19 pandemic and related public health measures, as well as the potential for a more permanent global shift to remote work; our ability to retain and upgrade paying users, and increase our recurring revenue; our ability to attract new users or convert registered users to paying users, our future financial performance, including trends in revenue, costs of revenue, gross profit or gross margin, operating expenses, paying users, and free cash flow; our history of net losses and our ability to maintain profitability; our liability for any unauthorized access to our data or our users' content, including through privacy and data security breaches, significant disruption of service on our platform or loss of content, particularly from any potential disruptions in the supply chain for hardware necessary to offer our services that may result from the COVID-19 pandemic; any decline in demand for our platform or for content collaboration solutions in general; changes in the interoperability of our platform across devices, operating systems, and third-party applications that we do not control; competition in our markets; our ability to respond to rapid technological changes, extend our platform, develop new features or products, or gain market acceptance for such new features or products, our ability to manage our growth or plan for future growth; our acquisition of other businesses and the potential of such acquisitions to require significant management attention, disrupt our business, or dilute stockholder value; our ability to attract and retain key personnel and highly qualified personnel; our capital allocation plans with respect to our stock repurchase program and other investments; and the dual class structure of our common stock and its effect of concentrating voting control with certain stockholders who held our capital stock prior to the completion of our initial public offering. These factors could cause actual results, performance or achievement to differ materially and adversely from those anticipated or implied in the forward-looking statements. Additional information will be available in other future reports that we may file with the SEC from time to time, which could cause actual results to vary from expectations. Except as required by law, Dropbox does not undertake any obligation to publicly update or revise any forward-looking statement, whether as a result of new information, future developments or otherwise. In addition to financial information presented in accordance with U.S. generally accepted accounting principles ("GAAP"), this presentation includes certain non-GAAP financial measures, including non-GAAP gross margin, non-GAAP operating income, non-GAAP operating expenses (including research and development, sales and marketing and general and administrative), non-GAAP operating margin and free cash flow. These non-GAAP measures are presented for supplemental informational purposes only and should not be considered a substitute for financial information presented in accordance with GAAP. These non-GAAP measures have limitations as analytical tools, and they should not be considered in isolation or as a substitute for analysis of other GAAP financial measures. The non-GAAP measures Dropbox uses may differ from the non-GAAP measures used by other companies. This presentation also contains statistical data, estimates and forecasts that are based on independent industry publications or other publicly available information, as well as other information based on our internal sources. This information may be based on many assumptions and limitations, and you are cautioned not to give undue weight to such information. We have not independently verified the accuracy or completeness of the data contained in the industry publications and other publicly available information. Dropbox does not undertake to update such data after the date of this presentation. All third-party logos appearing in this presentation are trademarks or registered trademarks of their respective holders. Any such appearance does not necessarily imply any affiliation with or endorsement of Dropbox. 2#3Business Overview 3#4Dropbox Today Leader in file sync and share Smart workspace for digital content collaboration Addressing individual and team workflows Leveraging virality and scale in go-to-market Balanced growth and cash flow generation model 4#5Global Collaboration Platform at Scale* 700M+ registered users 800B+ pieces of content 17.09M paying users 80% of subscribers use us for work *Data as of 3/31/22 Ps P Pr & A A TU Ai Pr A 5 P#6Keeping Files in Sync Cloud storage 2007 Backup & sync File sync and sharing & !!! Keeping Teams in Sync Beyond FSS Today Team collaboration Content management Professional sharing Secure sharing and analytics Project management eSignature Content backup 6#7Our Product Portfolio Individuals Basic Plus Professional Backup Teams Family Standard Advanced Enterprise Dropbox ✓ HELLOSIGN HelloSign HelloSign API HelloWorks HelloFax C Dropbox DocSend Personal Standard Advanced Enterprise 7#8Reinventing the Software Playbook Traditional playbook Designed for IT Top-down distribution Walled garden Rip-and-replace VS. VS. VS. VS. What sets Dropbox apart Designed for users Bottom-up adoption Open ecosystem Live side-by-side 8#9Efficient Go-to-Market Adopt organically Land Land within companies C Expand within companies Expand Deploy fully 131 9#10Growth Drivers Execute Convert and Retain Drive registered users to become paying users of Individual and Team plans Upsell Prompt existing users to upgrade to premium plans or purchase additional licenses and add-ons Innovate New product experiences Leverage scale and user insights to enhance existing products and drive adoption of new ones Expand into workflows Invest in integrations and native capabilities to enable more workflows beyond FSS 10#11New Features Help Organize Digital Content Dropbox introduces new tools to easily automate and maintain an organized file system Keeping digital content organized across work and home has become increasingly complex m Introducing features such as: ● ● .. ● Automated folders & dashboards Multi-file organize Naming conventions Tagging Document conversion 11#12New Product Experiences Dropbox introduces new product experiences for distributed teams and creatives D Capture An all-in-one visual communication tool that helps team members share their work and ideas asynchronously Replay A video collaboration tool that makes it easier to collect, manage, and respond to feedback, all in one place :: Shop A platform to sell digital content creations that users store in their Dropbox 12#13Dropbox Family Plan • Organize, centralize and protect your Family content Enhanced privacy and security features ● My e Delated Fes Paw Passwords ABD Manage what matters most Family Room 616 Keep your family connected xlu PIN Keep sensitive info safe 13#14Dropbox Business • Organize and centralize content around the needs of your team Collaborate in shared workspaces and streamline workflows Secure company data through visibility into content access and sharing ● DS DI Shared team workspace Admin Console Security Alerts Manage alert policies Unusual share outside your team What happened? What's at risk? Shared by Daniel Smith Number of files 548 Files shared Design team Eng team Severity ● Medium Category Information governance Date September 13, 2020 Shared with [email protected] +5 more File size 2 TB P 0 GAA Delete access Data governance and audit logs Dashboard 6 Members 0 12 5 Invites Licenses Joined Team management & centralized billing 14#15Dropbox Business Teams Expansion Dropbox now has over 600K paid plans for business teams (“Teams plans") Making it even easier to invite people to join your team • Team admins & members can now easily invite collaborators to join the team after sharing content with them ● Invite people to your Dropbox team Invite them to Hanford Inc. Dropbox, so they don't have to ask you each time they need access to files or more storage. J Ann Thompson [email protected] • @hanfordinc.com email match . Your team has shared 7 folders with them . Your team has worked with them since Aug 3, 2020 [email protected] • @hanfordinc.com email match . Your team has shared 7 folders with them . Your team has worked with them since Aug 3, 2020 [email protected] . Your team has shared 7 folders with them . Your team has worked with them since Aug 3, 2020 ✓ You'll be charged for 1 more person, and your new monthly total is $150.00. Watch for an email with all the details. Not now Invite Request an invite for [email protected] to join your Dropbox team Invite them to Hanford Inc. Dropbox, so they don't have to ask you each time they need access to files or more storage. Ann Thompson [email protected] Your requests will be sent to admins for approval. Not now Request invite -35% of paying users are on Teams plans 15#16HelloSign Update HelloSign launched HelloSign Templates HelloSign now integrates with Microsoft SharePoint • Launched the HelloSign Mobile App • Introduced paid premium support HelloSign is available in 21 additional languages ● V HELLOSIGN ● < HanfordInc_nda.pdf Non-Disclosure Agreement Share Share with Dropbox Send for Signature Open ▾ Q the *** 16#17DocSend Update ▸ Dropbox DocSend • DocSend is a full suite of self-serve products to manage document sharing and analytics through real-time controls and insights for: • Virtual data rooms for fundraising M&A ● Sales and marketing Investor relations ● ● • DocSend launched DocSend Dashboard Analytics • Bundled Dropbox Teams + DocSend offer launched in early 2022 • Rebranded Dropbox DocSend brings our offerings into a more seamless experience We are investing in adding new functionality into DocSend's adjacent workflows and continuing to improve the user experience ΣΟΘ Share Share with Dropbox Send a copy Send for signature Send and track Gmail Zoom Connect more apps 1s 17#18Dropbox + Command E Accelerating the Dropbox vision to become one organized place for content and all workflows around it • Command E is a universal search tool that allows users to quickly locate & access content across numerous apps and could content Dropbox + COMMAND E 18#19Deep Integration Partners Google il: slack ATLASSIAN BetterCloud A Adobe zoom Microsoft salesforce 19#20Environmental, Social, and Governance of Environmental Dropbox is committed to fighting global warming and reducing our carbon footprint. We're always looking at ways we can make a difference in our day-to-day business practices, and have set meaningful sustainability goals that we plan to accomplish by 2030. & Social Our DEI initiatives, workforce development programs, and ethical business practices all play a role in driving Social Responsibility at Dropbox. In addition, we also empower our employees to give back by providing paid volunteer time off, matching donations, and making product donations to nonprofits, through our Dropbox for Good program. Governance We're committed to maintaining an independent and diverse board of directors. Since 2019, we've added five directors who are women or members of underrepresented communities to our board. 20#21Financial Highlights 21#22Financial Highlights Predictable and balanced financial model Investing for continued revenue growth Driving strong operating leverage Significant share repurchases 22#23Dropbox Financial Strategy: Maintaining LT Margin Targets Dropbox 80%-82% Non-GAAP Gross Margin $1 Bn Free Cash Flow by 2024 30% -32% Non-GAAP Operating Margin *Note: Operating margin is non-GAAP and excludes stock-based compensation expense and certain non-recurring adjustments. Free cash flow is GAAP net cash provided by operating activities less capital expenditures. See appendix for non-GAAP reconciliation. 23#24Strong Performance at Scale $1,661 2019 $1,914 2020 $2,158 Revenue ($M) 2021 $392 2019 $491 2020 $708 2021 Free Cash Flow ($M) 76% 2019 79% 2020 81% 2021 Non-GAAP Gross Margin 12% 2019 21% 2020 30% *Note: Non-GAAP gross margin and non-GAAP operating margin exclude stock-based compensation expense and certain non-recurring adjustments. Free cash flow is GAAP net cash provided by operating activities less capital expenditures. See appendix for non-GAAP reconciliation. 2021 Non-GAAP Operating Margin 24#25Key Metrics $1,811 2019 $2,022 2020 ARR ($M) $2,261 2021 15.48 ÏÏÏ 2020 14.31 16.79 2019 2021 Paying Users (MM) $128.50 III 2020 $123.07 2019 $133.73 ARPU ($) 2021 25#26Q1'22 Financial Highlights $512 Q1 21 $562 Q1 22 Revenue ($M) $149 29% Q1 21 $170 30% Q1 22 Non-GAAP operating margin Operating Income ($M) Operating income is non-GAAP and excludes stock-based compensation expense and certain non-recurring adjustments. See appendix for non-GAAP reconciliation. 26#27Q1'22 Financial Highlights $2,112 Q1 21 ARR ($M) $2,290 Q1 22 15.83 Q1 21 17.09 Q1 22 Paying Users (M) $132.55 Q1 21 ARPU ($) $134.63 Q1 22 27#28Operating Leverage 09 Proprietary Infrastructure 수 Virtual First Workforce Optimization 28#29Updated Target Model Non-GAAP Gross Margin R&D expense as % of revenue S&M expense as % of revenue G&A expense as % of revenue Operating margin Annual Free Cash Flow 2019 76% 30% 23% 11% 12% $392M 2020 79% 28% 20% 10% 21% $491 M 2021 81% 25% 18% 8% 30% $708M Long-term target 80 - 82% 23-25% 18 - 20% 8 - 10% 30-32% $1B+ *Note: Margins and expenses exclude stock-based compensation expense and certain non-recurring adjustments. Free cash flow is GAAP net cash provided by operating activities less capital expenditures. See 29 appendix for non-GAAP reconciliation.#30Appendix 30#31Dropbox subscription plans Basic Free Dropbox Transfer* Dropbox Paper Computer Backup File requests 30 day version history HelloSign eSignatures Passwords 2GB of storage Backup $5.99/month $59.88 / year Dropbox Backup Personal Plus $11.99 / month $119.88 / year Everything in Basic and Backup** Passwords Vault* Dropbox Rewind Smart Sync and Smart Sync Auto-Evict Full text search Priority email support 2TB storage Family $19.99/month $203.88 / year Everything in Plus Up to 6 users Family Room folder 2TB storage Professional $19.99 / month $199.00/year Everything in Plus Auto OCR Image search Watermarking Shared link controls Branded sharing 180 day version history Premium previews Time-based comments Viewer history Traffic and insights 3TB storage Pro + eSign $31.99/month $299.88 / year Everything in Plus 5 templates for commonly signed documents Tamper-proofing Audit trail that tracks and time-stamps actions Built in data validation 180 day version history. Branded watermarking Live chat support Advanced sharing controls Standard + DocSend $83/user / month $600 /user / year 3 users minimum Everything in Standard Business Real-time document analytics Multiple documents with a single link Passcodes and email verification Approved viewer and domain lists. 5TB storage Standard $15.00 user / month $150.00 /user / year 3 users minimum Everything in Basic and Backup** Dropbox Rewind Smart Sync and Smart Sync Auto-Evict Auto OCR, Image and full text search Watermarking Shared link controls Branded sharing 180 day version history Team folders Admin console Granular permissions Active directory connector Enables HIPAA compliance Unlimited API access*** Priority email+ live chat. 5TB storage Advanced $25.00 user / month $240.00 /user / year 3 users minimum Everything in Standard Premium previews Time-based comments Viewer history Single sign-on integration (SSO) Audit logs Device approvals Tiered admin roles Business hours phone support As much storage as needed Enterprise Negotiated pricing Unlimited storage on one computer and one. external drive. 3TB storage; Send unlimited documents for signature *Vault is only available in Plus, Family, and Professional. *Size of Dropbox Transfer varies based on Dropbox plan: Basic (100MB), Plus, Family, & Standard (2GB), Professional, Advanced, and Enterprise (100GB). Professional, Advanced, and Enterprise plans also receive advanced Transfer functionality. 31 **Backup space limited to available storage for each SKU ***Teams have unlimited API access to productivity and security partners but may be subject to a cap on API calls to data transport partners. Everything in Advanced Enterprise mobility management (EMM) Network control Domain insights and account capture 24/7 phone support and advanced training As much storage as needed#32Non-GAAP reconciliation Income (loss) from operations - GAAP Stock-based compensation Acquisition-related and other expenses Amortization of acquired intangible assets Impairment related to real estate assets Workforce reduction expense Income from operations - Non-GAAP Non-GAAP operating margin 2019 $ $ (80.5) 261.2 15.9 8.4 205.0 12.3% Twelve Months Ended 2020 $ $ (277.0) 261.5 16.9 9.5 398.2 409.1 21.4% 2021 274.4 287.1 26.8 13.1 31.3 14.3 647.0 30.0% 32#33Non-GAAP reconciliation Income from operations - GAAP Stock-based compensation Acquisition-related and other expenses Amortization of acquired intangible assets Impairment related to real estate assets Workforce reduction expense Income from operations - Non-GAAP Non-GAAP operating margin Three Months Ended March 31, 2021 $ $ 42.5 67.9 5.7 2.4 17.3 12.8 148.6 29.1% March 31, 2022 $ $ 89.5 72.3 5.0 3.5 170.3 30.3% 33#34Free cash flow reconciliation Net Cash provided by operating actitivies Capital expenditures Free cash flow 2019 $ 528.5 (136.1) 392.4 Twelve Months Ended 2020 $ $ 570.8 (80.1) 490.7 2021 $ $ 729.8 (22.1) 707.7 34#35Non-GAAP reconciliation Gross profit Gross margin Research and development Research and development margin Sales and marketing Sales and marketing margin General and administrative General and administrative margin Impairment related to real estate assets Impairment related to real estate assets margin Income from operations Operating margin Note: % are rounded for presentation purposes GAAP $ 1,713.7 79% 755.9 35% 427.5 20% 224.6 10% 31.3 1% 274.4 13% Stock based compensation $ 23.2 1% (190.1) (9%) (25.0) (1%) (48.8) (2%) 287.1 13% Twelve Months Ended - 2021 Amortization of acquired intangible assets Acquisition- related and other expenses $ (19.7) (1%) (5.3) (1.8) 26.8 1% $ 6.0 (7.1) 13.1 1% Impairment related to real estate assets (31.3) (1%) 31.3 1% Workforce reduction expense $ 1.7 (3.2) (6.9) (2.5) 14.3 1% Non-GAAP $ 1,744.6 80% 542.9 25% 383.2 19% 171.5 8% 647.0 30% 35#36*Dropbox 36