#1Company Presentation May 2021 Dropbox#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 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 19, 2021, and include, but are not limited to, our ability to realize anticipated benefits to our business from our shift to a Virtual First work model as well as impacts to our financial results and business operations as a result of this shift; the impacts 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, in particular paying users impacted by the COVID-19 pandemic, and increase our recurring revenue; our ability to attract new users or convert registered users to paying users, in particular prospective paying users financially impacted by the COVID-19 pandemic; 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 achieve or 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, particularly in light of potential disruptions to the productivity of our employees that may result from our shift to a Virtual First work model; 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 550B+ pieces of content 15.83M paying users 80% of subscribers use us for work *Data as of 3/31/21 Ps P Pr & A A Ai Pr A 5 P#6Keeping Files in Sync Cloud storage 2007 Backup & sync File sync and sharing & 101. Keeping Teams in Sync Smart Workspace Today Team collaboration Content management Professional sharing Secure sharing and analytics Project management e Signature Personal privacy Content backup 6#7Our Product Portfolio Dropbox Individuals Teams Basic Plus Professional Family Standard Advanced Enterprise HELLOSIGN HelloSign HelloSign API HelloWorks HelloFax 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 Expand within companies Expand Deploy fully ane 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 10#11New Products and Features Transfer Your transfer is ready! Send PDF Vault 11#12New Products and Features Q Accounts a Popular G N Amazon [email protected] Dropbox [email protected] Passwords Add 51 a Amazon Username [email protected] Password O + Backup Dropbox My Computer My computer Desktop Documents Downloads Create Invite My Computer Desktop Documents a & ... Downloads •1 1 1 I 12#13Growing Portfolio of Add-on Products for Teams Advanced Team and Content Controls Data Governance Data Migration Creative Tools • Automated workflows for account capture, onboarding & off-boarding • Data Loss Prevention ● ● • Quickly migrate files from local or cloud storage into Dropbox Business Insightful analytics & comprehensive reporting ● Recover any files deleted or changed in the last 10 years Offered with or without Legal Hold capability ● Secure and easy large file previews and transfers • Review and aggregate frame-based commenting for large videos Integration with Adobe Creative Cloud ● 13#14Dropbox Family • 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 14#15Dropbox 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 24 A 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 0 Delete access Data governance and audit logs Dashboard 6 0 12 5 Members Invites Licenses Joined Team management & centralized billing 15#16HelloSign Update Native integration in Dropbox • 70%+ growth in end-user signature requests 60%+ growth in API transactions Launched in 21 additional languages • Increasing cross-sell velocity ● ● ● *Note: Growth rates reflect 2019-2020 period < HanfordInc_nda.pdf Non-Disclosure Agreement Share Share with Dropbox Send for Signature Open ▾ P. @ 2 سلاید *** 16#17DocSend Update Dropbox + DocSend • DocSend is a secure self-serve document sharing and analytics product • Current use cases revolve around content sharing and virtual data rooms for fundraising, M&A, sales and marketing, and investor relations • Similar go to market strategy to Dropbox leveraging self-serve business • Full suite of self-serve products to manage end-to-end document workflow: creation, sharing, signature 17#18Open ecosystem Enterprise apps IBM SAP ADP Media + Design DocuSign A Adobe A AUTODESK ORACLE vimeo Canva Sales + Marketing salesforce HELLOSIGN zendesk ZOHO Hootsuite Project management A ATLASSIAN asana Wrike ✓smartsheet Content management NINTEX Microsoft Azure SharePoint WWIDEN" BitTitan Productivity Office A Adobe Security O vmware® Google Workspace splunk> Better Cloud slack Symantec Communications okta zoom Workplace 60B+ API calls /month 1M+ registered developers 35% more spent each month by integration MAUS (IMAUS) compared to non-iMAUS 85% of active, paid Dropbox teams have linked a third- party app 18#19Deep Integration Partners Google il: slack ATLASSIAN BetterCloud A Adobe zoom Microsoft salesforce 19#20Financial Highlights 20#21Financial Highlights Significant revenue and cash flow scale Predictable and balanced financial model Investing for continued revenue growth Driving for strong operating leverage 21#22Strong Performance at Scale $1,392 2018 $1,661 2019 Revenue ($M) $1,914 2020 $362 2018 $392 2019 $491 2020 Free Cash Flow ($M) 75% 2018 76% 2019 79% 2020 12% 2018 12% 2019 21% *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. 2020 Non-GAAP Gross Margin Non-GAAP Operating Margin 22#23Key Metrics $1,510 2018 $1,811 2019 ARR ($M) $2,022 2020 12.70 2018 14.31 2019 Paying Users (MM) 15.48 2020 $117.64 2018 $123.07 2019 ARPU ($) $128.50 2020 23#24Q1'21 Financial Highlights $455 Q1 20 Revenue ($M) $512 Q1 21 $73 16% $149 Q1 20 - Non-GAAP operating margin Operating income is non-GAAP and excludes stock-based compensation expense and certain non-recurring adjustments. See appendix for non-GAAP reconciliation. 29% Q1 21 Operating Income ($M) 24#25Q1'21 Financial Highlights $2,052 Q4 20 ARR ($M) $2,112 Q1 21 Current period exchange rate applied to Q4'20 ARR to show constant currency ARR growth 15.48 Q4 20 15.83 Q1 21 Paying Users (M) $130.17 Q4 20 $132.55 ARPU ($) Q1 21 25#26Mix-shift to Premium Plans % Paying Users on Premium Plans 5% Q4'17 20% Q1'21 *Note: Figures exclude HelloSign. Premium plans refer to Dropbox Professional and Dropbox Advanced. 4x Increase in the attach rate of users to premium plans 26#27Operating Leverage ① Proprietary Infrastructure 보 Virtual First Workforce Optimization 27#28Target 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% $491M Long-term target 78 - 80% 23-25% 18 - 20% 8 - 10% 28 - 30% $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 appendix for non-GAAP reconciliation. 28#29Appendix 29#30Dropbox subscription plans Free Basic Dropbox Transfer* Dropbox Paper Computer Backup File requests 30 day version history HelloSign eSignatures Passwords 2GB of storage Plus $11.99 / month $119.88 / year Everything in Basic Passwords Vault* Dropbox Rewind Smart Sync and Smart Sync Auto-Evict Full text search Priority email support 2TB storage Personal 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 Standard $15.00/user / month $150.00 /user/year 3 users minimum Everything in Basic Business 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 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 30 *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. **Teams have unlimited API access to productivity and security partners but may be subject to a cap on API calls to data transport partners.#31HelloSign Subscription Plans FREE $0 1 user 0 Templates 3 req / mo Audit Trail Notification Signer fields and more.... HELLOSIGN ESSENTIAL $15 / user / mo 1 user 5 Templates Unlimited reqs Includes Free Data validation Multiple languages Tamper-proofing Template Links and more.... STANDARD $25 user / mo Minimum 2 users 15 Templates Unlimited reqs Includes Ess. Branding Bulk send Salesforce integrations SMS auth. and more.... Plans include unlimited document storage in HelloSign or Prebuilt storage integrations with Dropbox and several others $ Additional cost add-on * Higher API volume tiers available, up to 300K per month PREMIUM $40 /user / mo Minimum 5 users Unlimited Templates Unlimited reqs Includes Std. Adv. signing tools Adv. signer fields Adv. reporting Multi-teams$ and more.... FREE Build & Test our API for Free ✓ HELLOSIGN API ESSENTIAL $75/mo 5 Templates Starts 50 reqs / mo* API dashboard Audit trail Data validation SDKS in 6 languages Signer fields and more.... STANDARD $250 / mo 15 Templates Starts 100 reqs / mo* Includes Ess. Branding Bulk send Embedded signing Signer attachments and more.... Plans include unlimited document storage in HelloSign PREMIUM $400 / mo Unlimited Templates Starts 100 reqs / mo* Includes Std. Adv. signing tools Adv. signer fields Embedded templates White labeling$ and more.... 31#32DocSend Subscription Plans D DocSend Document Analytics Basic Document Security (Require email, Redirect downloading, Expiration & Passwords) Spaces Mail Merge Links eSignature Integrations * Advanced Security Features (1-Click NDA, Watermarking, Allowed viewer list, email auth.) Advanced Spaces Features (Folders, Granular Space Permission) Campaign Links (SSO) Integration Sub-Team Permissions Storage Personal For individuals who want secure sharing and document insights $10 /mo /per user billed annually $15 /mo /per user billed monthly Basics Only I I 10 GB /user 2 GB Standard For business teams that need best-in- class document sharing and team management $45 /month per user billed annually $65/month per user billed monthly Basics plus add-ons available Upload large documents *Integrations note that Basics only includes Dropbox, Gmail, and Outlook. Add-ons available for additional cost 50 GB /user 2 GB Advanced For deal management professionals that need advanced security or integrations Includes 3 users $150 / month billed annually Add'l users $60/month $250 / month billed monthly Add'l users $60/ month Basics plus add-ons available Add-on Add-on 50 GB /user 2 GB Enterprise For larger teams Plans start at $5,000 50 GB /user 2 GB 32#33Definitions Total Annual Recurring Revenue, ("Total ARR" or "ARR") - represents the amount of revenue that we expect to recur, enables measurement of the progress of our business initiatives, and serves as an indicator of future growth. We calculate Total ARR as the number of users who have active paid licenses for access to our platform as of the end of the period, multiplied by their annualized subscription price to our platform. We adjust the exchange rates used to calculate Total ARR on an annual basis at the beginning of each fiscal year. Average Revenue per Paying User, (“ARPU”) – is defined as our revenue for the period presented divided by the average paying users during the same period. For interim periods, we use annualized revenue, which is calculated by dividing the revenue for the particular period by the number of days in that period and multiplying this value by 365 days. Average paying users are calculated based on adding the number of paying users as of the beginning of the period to the number of paying users as of the end of the period, and then dividing by two. Paying Users are defined as the number of users who have active paid licenses for access to our platform as of the end of the period. One person would count as multiple paying users if the person had more than one active license. For example, a 50-person Dropbox Business team would count as 50 paying users, and an individual Dropbox Plus user would count as one paying user. If that individual Dropbox Plus user was also part of the 50-person Dropbox Business team, we would count the individual as two paying users. 33#34Non-GAAP reconciliation Income from operations - GAAP Stock-based compensation Acquisition-related and other expenses Amortization of acquired intangible assets Impairement related to real estate assets Workforce reduction expense Income from operations - Non-GAAP Non-GAAP operating margin $ $ Three Months Ended March 31, 2020 26.8 $ 39.8 4.2 2.3 73.1 16.1% $ March 31, 2021 42.5 67.9 5.7 2.40 17.3 12.8 148.6 29.1% 34#35Non-GAAP reconciliation Net Cash provided by operating actitivies Capital expenditures Free cash flow $ $ December 31, 2018 425.4 (63.0) 362.4 Twelve Months Ended December 31, 2019 528.5 (136.1) 392.4 $ December 31, 2020 570.8 (80.1) 490.7 35#36Non-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 (loss) from operations Operating margin Note: % may not foot due to rounding $ GAAP 1,499.3 78.3 % 727.5 38.0 % 422.8 22.1% 227.8 11.9% 398.2 20.8% (277.0) (14.5%) $ Stock based compensation 17.1 0.9 % (174.1) (9.1%) (33.7) (1.8%) (36.6) (1.9%) 261.5 13.7 % Twelve Months Ended - 2020 Acquisition- related and other expenses $ (16.8) (0.9%) (0.1) 16.9 0.9 % Amortization of acquired intangible assets 3.9 0.2% $ (5.6) (0.3%) I 9.5 0.5% $ Impairment related to real estate assets (398.2) (20.8%) 398.2 20.8% $ Non-GAAP 1,520.3 79.4 % 536.6 28.0% 383.5 20.0 % 191.1 10.0 % - % 409.1 21.4% 36#37Non-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 Income (loss) from operations Operating margin Note: % may not foot due to rounding $ GAAP 1,250.3 75.3% 662.1 39.9 % 423.3 25.5% 245.4 14.8 % (80.5) (4.8%) $ Stock based compensation 15.8 1.0 % (147.6) (8.9%) (31.4) Twelve Months Ended - 2019 (1.9%) (66.4) (4.0%) 261.2 15.7 % Acquisition-related and other expenses $ (14.5) (0.9%) (1.4) (0.1%) 15.9 1.0 % Amortization of acquired intangible $ assets 3.4 $ 0.2 % (5.0) (0.3%) 8.4 0.5% Non-GAAP 1,269.5 76.4% 500.0 30.1 % 386.9 23.3 % 177.6 10.7 % 205.0 12.3 % 37#38Non-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 Income (loss) from operations Operating margin Note: % may not foot due to rounding $ GAAP 997.0 71.6 % 768.2 55.2 % 439.6 31.6% 283.2 20.3 % (494.0) (35.5%) $ Twelve Months Ended - 2018 Stock based compensation 47.0 3.4 % (368.2) (26.5%) (94.3) (6.7%) (140.6) (10.0%) 650.1 46.7 % Employer payroll related to the release of two-tier RSUS $ 1.1 0.1% (8.3) (0.6%) (2.2) (0.2)% (2.3) (0.2%) 13.9 1.0 % $ Non-GAAP 1,045.1 75.1 % 391.7 28.1% 343.1 24.7% 140.3 10.1 % 170.0 12.2 % 38#39*Dropbox