#1Dropbox Company Presentation November 2020#2Safe harbor Statement This presentation contains forward-looking statements. These statements may relate to, but are not limited to, Dropbox, Inc.'s ("Dropbox," "we," "us," or similar terms)plans for growth, technological capabilities and new features and products, and long-term financial targets, as well as assumptions relating to the foregoing. 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 quarterly report on Form 10-Q for the fiscal quarter ended June 30, 2020 that we filed with the Securities and Exchange Commission (the "SEC") on August 7, 2020, 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, cost 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; the demand for our platform or for content collaboration solutions in general; possible harm caused by significant disruption of service, particularly from any potential disruptions in the supply chain for hardware necessary to offer our services that may result from the COVID-19 pandemic, or loss or unauthorized access to users' content; our ability to effectively interoperate our platform with others; our ability to successfully integrate acquired businesses; our ability to continue to release, gain customer acceptance of, and provide support for, additional product features and new and improved versions of our services, 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 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; our ability to realize benefits from strategic partnerships; our ability to compete successfully in competitive markets; 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 made available in our quarterly report on Form 10-Q for the quarter ended September 30, 2020 and in other 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 expenses (including research and development, sales and marketing and general and administrative), non-GAAP operating income, 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. A reconciliation of these measures to the most directly comparable GAAP measures is included at the end of this presentation. A reconciliation of our forward-looking guidance for non-GAAP operating margin with our forward-looking GAAP operating margin, forward-looking guidance for non-GAAP operating expenses with our forward-looking GAAP operating expenses and forward-looking guidance for non-GAAP gross margin with our forward-looking GAAP gross margin is not available without unreasonable efforts as the quantification of stock- based compensation expense, which is excluded from our non-GAAP operating and gross margins and operating expenses and will have a significant impact on our GAAP operating and gross margins and operating expenses, requires additional inputs that are difficult to predict and subject to change. Our forward-looking guidance for non-GAAP operating and gross margins and operating expenses also excludes the following expenses related to the acquisition of HelloSign: the unpaid portion of the purchase price for certain executives that is being earned over three years if they remain employed in the total amount of $28 million; and amortization of acquired intangible assets, which are subject to valuation efforts. 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.#3Keeping files in sync Cloud storage 2007 Backup & sync File sharing Shared folders |||| = & Keeping teams in sync Smart Workspace Today Content management Collaborative apps Professional sharing Project management eSignature Personal Privacy Content Backup#4Dropbox today We're a business software company that defies traditional boundaries We're a smart workspace for the world's digital content We have a rare combination of virality, scale, and cash generation We have a long runway for growth#5Global collaboration platform at scale 600M+ registered users 550B+ pieces of content 15.25M paying users 80% of subscribers use us for work 31 00 S Ps * Ai W#6Reinventing 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#7Efficient Go-to-Market Self-serve "land" Starts with massive user adoption Land within companies Expand within companies Targeted outbound "expand" Full deployment#8Open ecosystem Enterprise apps Sales + Marketing IBM SAP ADP Media + Design DocuSign A Adobe A AUTODESK ORACLE® vimeo Canva salesforce V 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> BetterCloud slack Tip Workplace Symantec. Communications okta zoom 60B+ API calls /month 85% of active, paid Dropbox teams have linked a third-party app 1M+ registered developers#9Hybrid infrastructure: Scale, Agility, & Innovation Seattle Hillsboro Palo Alto San Jose Los Angeles IDC AICPA SOC ISO Dallas Denver cloud CSA security alliance Chicago Amsterdam. Toronto London New York Paris Ashburn Madrid- Atlanta Miami Core DC POP Oslo Stockholm Berlin Frankfurt Milan Public DC Hong Kong Singapore Tokyo Sydney#10Growth Drivers Execute Convert Drive registered users to become paying users on Individual and Team plans Upsell Prompt existing paying users to upgrade to premium plans or purchase additional licenses Innovate New product experiences Leverage scale and user insights to enhance existing products and drive adoption of new ones Expand ecosystem Grow thriving ecosystem to put Dropbox at the center of users' lives#11Product updates#12The New Dropbox Brings together cloud content and traditional files in one place Brings tools together by integrating with best-of-breed apps Brings people together by transforming folders into rich workspaces En Hanford Inc. E Starred folders Customer Proposal Suggested folders + Work [email protected] < > Hanford Inc. > > Sales Customer Proposal Q Search Robert Hakobyan updated 3 hours ago Create Name Recent activity A 69 ⠀ Invite Q Search Hanford Inc. For you Recent Notifications Meeting: Weekly Sync 10:00am-10:30am - Meeting Room 1 Attach Join Zoom meeting ✓ Suggested attachments Timeline.gsheet Brainstorm.paper Your highlights + Final Proposal.pdf o Viewed 3 hours ago Sales Team highlights + Attach * Michelle Wallace edited Customer Info.gdoc 2 hours ago. You work with Michelle a lot.#13Dropbox Transfer Easily and securely share large files and folders Recipients can view, download, and comment on Transfers Senders receive analytics and real- time notifications around file activity Note: Size of Transfers varies based on Dropbox plan: Basic (100MB), Plus & Standard (2GB), Professional, Advanced, Enterprise, and Education (100GB). Note: Transfers are automatically set to expire after 7 days, but Professional, Advanced, Enterprise, and Education users have the option to set the transfer to expire in 7, 30, 60, or 90 days. BEE PDF CO. 5 files from Company Inc. 3.6 GB - Expires in 7 days Save to my Dropbox Download Transfers Colors.psd and 6 more Q Search 3 Visits 6 Visits 5 Visits 13 Visits C 2 Downloads 4 Downloads 5 Downloads 8 Downloads ⠀#14Dropbox Passwords Store and sync passwords across all devices Easily sign in from anywhere Zero-knowledge encryption keeps users' data secure Q Accounts F N N Dropbox [email protected] Facebook [email protected] Add [2 ... Facebook Userna Accounts Angela@ Passwo C N Dropbox [email protected] Facebook [email protected] + 0#15Dropbox Vault Securely store passports, tax documents, and financial statements PIN code provides extra layer of security Designate trusted friends and family access to your Vault Home Overview fol PDF Vault Jacob's Passport Create =#16Computer Backup Automatically back-up folders on a PC or Mac Content is continuously synced between the cloud and a hard drive Easily access all your content from within Dropbox Dropbox My Computer My computer Desktop Documents Downloads Create ✓ Invite My Computer Desktop Documents Downloads a ... + •1 ⠀ ⠀ ⠀#17Dropbox Family Keep your family's digital lives connected Create both shared and personal spaces Support up to 6 members in one plan Personal <> Dropbox Personal account Name Family Your family You can invite up to 5 other members, ages 13 and up. Kathryn Martinez Ashley Martinez Erik Martinez 3/5 invites left Dropbox Status Family manager Family member Family member Invite members 4 ✩ 0#18HelloSign Native Integration Sign, send, and receive documents all without ever leaving Dropbox Manage an entire end-to-end workflow within Dropbox HelloSign is now the primary eSignature tool for Dropbox users onboarding_nda.pdf NON-DISCLOSURE AGREEMENT Share onboarding_nda.pdf Details Open Activity Get it signed You sent this document for signature to [email protected] You created this document A L the#19Add-ons BetterCloud Extended Version History Data Migration Creative Tools Automated workflows for account capture, onboarding, & off boarding Data loss prevention Recover any file deleted or changed in the last 10 years Offered with or without legal holds Quickly migrate files from local or cloud storage into Dropbox Business Insightful analytics & comprehensive reporting Secure and easy large file transfers Preview capability for large files Integration with Adobe Creative Cloud#20Drobox App Center Discover and connect apps to your Dropbox account Over 40+ apps to choose from across a range of categories Creates a more engaging and higher- value experience with Dropbox App Center Collections Manage Q Search apps A chunk#21Deep integration partners Google zoom A Adobe BetterCloud slack Microsoft A ATLASSIAN salesforce#22Financial highlights#23Financial highlights Revenue ($M) $1,107 2017 $428 $1,392 14% YOY growth in Q3'20 3Q 19 2018 $487 3Q 20 $1,661 2019 Figures presented are non-GAAP and exclude stock-based compensation expense and certain non- recurring adjustments. See appendix for non-GAAP reconciliation. Operating income ($M) $60 5% 2017 $56 13% $170 Non-GAAP operating income Non-GAAP operating margin 3Q 19 12% 2018 $112 23% 3Q 20 $205 12% 2019#24Financial highlights ARR ($M) $1,530 2018 12% YOY growth in Q3'20 $1,766 3Q 19 $1,820 2019 $1,981 3Q 20 ARPU ($) $117.64 2018 3.9% YOY growth in Q3'20 $123.15 3Q 19 $123.07 2019 $128.03 3Q 20#25Target 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 Note: Margin framework excludes stock-based compensation expense and certain non-recurring adjustments. See appendix for non-GAAP reconciliation. Long-term target 78-80% 23-25% 18-20% 8-10% 28-30% $1B+#26Appendix#27Dropbox subscription plans Free Basic Dropbox Transfer* Dropbox Paper Computer Backup File requests 30 day version history HelloSign eSignatures Plus $11.99 / month $119.88 / year Personal Everything in Basic Passwords Vault* Dropbox Rewind Smart Sync and Smart Sync Auto-Evict Full text search Priority email support Family $19.99 / month $203.88 / year Everything in Plus Up to 6 users Family Room folder 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 Business Standard $15.00/user / month $150.00/user / year 3 users minimum Everything in Basic 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 ** 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 Enterprise As much storage as needed Negotiated pricing Everything in Advanced Enterprise mobility management (EMM) Network control Domain insights and account capture 24/7 phone support and advanced training 5TB storage 2TB storage 3TB storage 2GB of storage 2TB storage *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. As much storage as needed#28HelloSign subscription plans Free $0 1 user 3 docs/mo Audit trail Notifications Essentials $15 / mo 1 user 5 templates Unlimited Requests V HELLOSIGN Everything in Free 2-factor auth Template links Decline to sign Business $8 / user / mo Minimum 5 users Starts at 5 templates Unlimited Requests Everything in Pro Custom branding In-person signing Team features Enterprise* $24/ user / mo Minimum 5 users Unlimited templates Unlimited Requests Everything in Business Signer attachments Advanced signing Advanced reporting Team management Master account billing HIPAA (w/ BAA) CRM/CPQ Integration** Unlimited document storage in HelloSign or Prebuilt storage integrations with Dropbox and several others Bronze $99 / mo 50 API calls 5 templates Test mode Decline to sign Optional signers Audit trail Notifications Silver $249 / mo 150 API calls 15 templates HELLOSIGN API Everything in Bronze Embedded signing Embedded requesting Single foreign language Gold $449 / mo 450 API calls Unlimited templates Everything in Silver Multi-foreign languages Advanced signing Custom branding Signer attachments Bulk send Unlimited document storage in HelloSign +Prices are shown as price per month when paid annually *Additional Enterprise+ plan available with advanced functionality **Salesforce Sales Cloud, Salesforce CPQ and Oracle CPQ add-ons available at an additional $4/$12/$12/user per month respectively ***Higher volume API plans with advanced functionality available Enterprise*** Negotiated pricing 1,000+ API calls Unlimited templates Everything in Gold Embedded templates White labeling Data deletion HIPAA (w/ BAA)#29HelloWorks subscription plans SMB HW Free $0 / mo Up to 100 txns* mo Unlimited Users/Teams Unlimited Workflows Unlimited Participants HelloWorks Portal API Access Shareable Links Conditional Logic Unlimited Storage HW 150 $299 / mo Up to 150 txns* / mo Everything in Free Company Branding SMS Authentication Unlimited Storage Mid Market HW 250 $399 / mo Up to 250 txns* Unlimited Storage mo HW 450 $699 / mo Up to 450 txns* / mo Unlimited Storage *Any time a workflow is launched (or sent out) for completion a single (1) "Transaction" (txn) is created ENT HW 1K+ Negotiated Pricing Starts at 1,000 txns* / mo Everything in Mid Market Delegated Authentication Unlimited Storage#30HelloFax subscription plans Free 1 user 5 pages Single fax line** Int'l coverage Edit & sign Home Office $9.99 / mo 5 users 300 pages / mo Everything in Free Email to fax Receive faxes Multi-recipient faxes API access*** Professional $19.99 / mo 10 users 500 pages / mo Small Business $39.99 / mo 20 users 1,000 pages / mo Enterprise* Unlimited document storage in HelloFax or Prebuilt storage integrations with Dropbox and several others Negotiated pricing 20+ users Starts at 2,000 pages / mo Everything in Home Office Everything in Professional Everything in Small Business *Higher volume plans available with advanced features **Additional fax lines available for $4.99 / month ***API access available for an add-on fee of $2 / month per line and $0.05 / page with a $100 minimum monthly fee#31Non-GAAP reconciliation Loss from operations - GAAP Stock-based compensation Donation of common stock to the Dropbox Foundation Employer payroll taxes related to the release of two-tier RSUS Acquisition-related and other expenses Amortization of acquired intangible assets Income from operations - Non-GAAP $ 2017 (113.7) 164.6 9.4 60.3 Twelve months ended 2018 $ $ (494.0) 650.1 13.9 170.0 $ 2019 (80.5) 261.2 15.9 8.4 205.0#32Non-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 $ GAAP 1,250.3 75% 662.1 40% 423.3 26% 245.4 15% (80.5) -5% Stock-based compensation Twelve months ended - 2019 15.8 1% (147.6) -9% (31.4) -2% (66.4) -4% 261.2 16% Acquisition-related and other expenses 0% (14.5) -1% 0% (1.4) 0% 15.9 1% Amortization of acquired intangible $ assets 3.4 0% 0% (5.0) 0% 0% 8.4 1% $ Non-GAAP 1,269.5 76% 500.0 30% 386.9 23% 177.6 11% 205.0 12%#33Non-GAAP reconciliation Twelve months ended - 2019 Net cash provided by operating activities Capital expenditures Free cash flow $ $ 528.5 (136.1) 392.4#34Non-GAAP reconciliation Income (Loss) from operations - GAAP Stock-based compensation Acquisition-related and other expenses Amortization of acquired intangible assets Income from operations - Non-GAAP $ $ Three months ended September 30, 2019 (18.6) $ 68.2 4.0 2.4 56.0 $ September 30, 2020 30.0 75.7 4.1 2.4 112.2#35*Dropbox