#1◆Dropbox Company Presentation May 2023#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, 2022 that we filed with the Securities and Exchange Commission (the "SEC") on February 23, 2023, 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 general macro economic, political and market uncertainty, 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 ability to achieve and 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; 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 IN#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 17.90M paying users *Data as of 3/31/2023 Ps P Pr & A A Ai Pr A 5 F#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 Template Libraries 6#7Our Product Portfolio Individuals Teams Basic Plus Family Professional Standard Advanced Enterprise Dropbox Dropbox Sign Dropbox Sign Dropbox Sign API Dropbox Forms Dropbox Fax C Dropbox DocSend FormSwift from Dropbox Premium Annual Monthly Subscription 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 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 Introducing features such as: ● ● ● ● .. ● Automated folders & dashboards Multi-file organize Naming conventions Tagging Document conversion 11#12Video Workflows Dropbox is developing 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 DocSend A video and presentation sharing platform with advanced analytics to see what your visitors are really watching 12#13Dropbox Family Plan Organize, centralize and protect your Family content ● • Enhanced privacy and security features ● * Password Passwords Q 31 SAB Manage what matters most Family Room 66 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 2 0 C4 A Delete access Data governance and audit logs Admin Console Insights Insights 792 4.3 TB Mar 10 What's shared outside your team? Create report Numbers to watch 15,641 547 184 G4A 57 76% Ⓡ Advanced security alerts & notifications 14#15Dropbox Business Teams Expansion Dropbox has ~600K business teams 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. 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 ✓ Not now ✓ You'll be charged for 1 more person, and your new monthly total is $150.00. Watch for an email with all the details. 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#16● ● ● ● ● Dropbox Sign Update Dropbox Sign Dropbox Forms included in Standard and Premium Sign Plans Dropbox Sign API standardized on OpenAPI, delivering a better developer experience and feature complete SDKs Dropbox Sign API released a completely rebuilt API dashboard for developers Dropbox Sign is available in 21 additional languages Dropbox Sign customers can now edit signature requests after sending Dropbox Sign Sign documents Bulk send Home Templates Documents Teams Hi Matthew! 28 • Pending 20 • Drafts Drag documents here to get signed Create a template 55 • Signed 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 • Launched DocSend Dashboard Analytics last year • Launched Advanced Video Analytics in October Offering DocSend-powered analytics as a freemium experience to Dropbox individual users Share Share with Dropbox → Send a copy Send for signature Send and track Gmail Zoom Connect more apps 1 s 17#18Capture Update Dropbox Capture • In October, Capture became available across all Dropbox Plans: ● • Customers on Professional and Team plans can record videos in 4K up to the plan's storage limit and edit videos of any length Customers on Basic, Plus and Family plans get up to two hours of recording time at 1080p and editing for videos under 5 minutes Capture customers are creating over 150K+ captures each month Dropbox Capture Screenshot Screen recording Screen recording + camera GIF Audio recording Camera Show less 17#19Deep Integration Partners Google il: slack A ATLASSIAN Better Cloud A Adobe zoom Microsoft salesforce 19#20Environmental, Social, and Governance Dropbox published its first ESG Impact Report in October, which shares data for 2021. f % Environmental Social Dropbox is committed to fighting climate change 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. As of Dec 2021, we've sourced 100% renewable electricity for our operations, including our data centers. 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. The full report and more information can be found at dropbox.com/esg 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 Long-Term 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 $2,158 $1,914 ÏÏI 2020 2021 $2,325 Revenue ($M) 2022 $491 2020 $708 2021 $764 2022 Free Cash Flow ($M) 79% 2020 81% 2021 Non-GAAP Gross Margin 82% 2022 21% 2020 30% 2021 31% *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. 2022 Non-GAAP Operating Margin 24#25Key Metrics $2,250 17.77 16.79 III ÏÏÏ 2021 2021 $2,022 2020 $2,514 CC ARR ($M) 2022 15.48 2020 2022 Paying Users (MM) $128.50 2020 $133.73 2021 ARPU ($) $134.51 2022 25#26Q1'23 Financial Highlights $562 Q1 22 Revenue ($M) $611 Q1 23 $170 30% $175 29% Q1 23 Q1 22 Non-GAAP operating margin Operating Income ($M) Operating income is non-GAAP and excludes stock-based compensation expense and certain non-recurring adjustments. See appendix for non-GAAP reconciliation. 26#27Operating Leverage Proprietary Infrastructure 보 Virtual First Workforce Optimization 27#28Long-Term 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 2020 79% 28% 20% 10% 21% $491M 2021 81% 25% 18% 8% 30% $708M 2022 82% 28% 16% 7% 31% $764M 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 28 appendix for non-GAAP reconciliation.#29Appendix 30#30Non-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 $ 2020 (277.0) 261.5 16.9 9.5 398.2 409.1 21.4% $ Twelve Months Ended 2021 274.4 287.1 26.8 13.1 31.3 14.3 647.0 30.0 % $ $ 2022 181.3 330.7 18.0 13.8 175.2 719.0 30.9 %#31Non-GAAP reconciliation Income from operations - GAAP Stock-based compensation Acquisition-related and other expenses Amortization of acquired intangible assets Income from operations - Non-GAAP Non-GAAP operating margin $ Three Months Ended March 31, 2022 89.5 72.3 5.0 3.5 170.3 30.3 % $ March 31, 2023 84.1 76.0 7.4 7.0 174.5 28.6%#32Free cash flow reconciliation Net Cash provided by operating activities Capital expenditures Free cash flow $ $ 2020 570.8 (80.1) 490.7 $ $ Twelve Months Ended 2021 729.8 (22.1) 707.7 $ 2022 797.3 (33.8) 763.5#33Non-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 from operations Operating margin Note: % are rounded for presentation purposes $ GAAP 494.3 81% 235.2 38% 119.2 20% 55.8 9% 84.1 14% $ Three Months Ended March 31,2023 Stock based compensation 5.4 1% (52.9) (9%) (5.5) (1%) (12.2) (2%) 76.0 12% Acquisition- related and other expenses $ -% (5.4) (1%) (1.7) -% (0.3) -% 7.4 1% Amortization of acquired intangible assets $ 3.6 1% -% (3.4) (1%) -% 7.0 1% $ Non-GAAP 503.3 82% 176.9 29% 108.6 18% 43.3 7% 174.5 29%#34Non-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 from operations Operating margin Note: % are rounded for presentation purposes GAAP 449.5 80% 210.8 37% 95.7 17% 53.5 10% 89.5 16% $ Three Months Ended March 31,2022 Acquisition- related and other expenses Stock based compensation 5.7 1% (50.5) (9%) (4.5) (1%) (11.6) (2%) 72.3 13% $ -% (3.2) (1%) (1.7) -% (0.1) -% 5.0 1% Amortization of acquired intangible assets 2.0 -% $ -% (1.5) -% T -% 3.5 1% $ Non-GAAP 457.2 81% 157.1 28% 88.0 16% 41.8 7% 170.3 30%#35Dropbox subscription plans Basic Free Dropbox Transfer* Dropbox Paper Dropbox Computer Backup File requests 30 day version history 3 Sign eSignatures Dropbox Passwords Dropbox Capture* Personal Plus $11.99 / month $119.88 / year Everything in Basic Full text search Vault* Offline mobile folders Dropbox Rewind Remote device wipe Smart Sync and Smart Sync Auto-Evict Priority email support Family $19.99/month $203.88 / year Everything in Plus Up to 6 users Family Room folder Professional $19.99/month $198.96 / year Everything in Plus Auto OCR & Image search Shared link controls Branded sharing Adv. Dropbox Transfer* 180 day version history Premium previews Time-based comments Document watermarking Viewer history Traffic and insights Adv. Dropbox Capture* Live chat support Pro + eSign $31.99/month $299.88 / year Everything in Pro Unlimited Sign eSignatures 5 templates for commonly signed documents Tamper-proofing Audit trail that tracks and time-stamps actions Built in data validation Standard Business $18.00 /user / month $180.00/user / year 3 users minimum Everything in Plus External sharing reporting Auto OCR & Image Search Document Watermarking Shared link controls Branded sharing Adv. Dropbox Capture* 180 day version history Team folders Admin console Granular permissions Enables HIPAA compliance Unlimited API access** Priority email + live chat support Standard + DocSend $83/user / month $600/user/year 3 users minimum Everything in Standard Real-time document analytics Multiple documents with a single link Passcodes and email verification Approved viewer and domain lists Virtual Data Room folders Advanced $30.00/ user / month $288.00 /user / year 3 users minimum Everything in Standard Ransomware detection & recovery Adv. Dropbox Transfer* 1-year Extended version history Premium previews Time-based comments Viewer history Single sign-on integration (SSO) Audit logs Device approvals Tiered admin roles. Business hours phone support Enterprise Negotiated pricing Everything in Advanced Enterprise mobility management (EMM) Network control Domain insights and account capture 24/7 phone support and advanced training 31 As much storage as needed As much storage as needed 3TB storage 5TB storage (pooled) 3TB storage 5TB storage (pooled) 2TB 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. Basic, Plus, and Family only have 2 hours of Capture recording time. Pro, Standard and Advanced have unlimited Capture recording time and editing features. **Teams have unlimited API access to productivity and security partners but may be subject to a cap on API calls to data transport partners.#36*Dropbox 36