#1Datto Investor Presentation February 2022 datto#2Safe Harbor Forward-Looking Statements This presentation contains forward-looking statements that reflect Datto's current expectations and projections with respect to, among other things, its financial condition, results of operations, plans, objectives, future performance and business. These statements may be preceded by, followed by or include the words "anticipate," "estimate," "expect," "project,” “plan,” “intend,” “believe,” “may,” “will,” “should,” “can have," "likely," "goal," "target" and the negatives thereof and other words and terms of similar meaning. Further information on potential factors that could affect our results is included in our Annual Report on Form 10-K and our Quarterly Reports on Form 10-Q. Forward-looking statements include all statements that are not historical facts. Such forward-looking statements are subject to various risks and uncertainties. Accordingly, there are or will be important factors that could cause actual outcomes or results to differ materially from those indicated in these statements. There is no assurance that any forward-looking statements will materialize. You are cautioned not to place undue reliance on forward-looking statements, which reflect expectations only as of this date. Datto does not undertake any obligation to publicly update or review any forward-looking statement, whether as a result of new information, future developments or otherwise. Market and Industry Data This presentation includes information concerning economic conditions, Datto's industry, Datto's markets and Datto's competitive position that is based on a variety of sources, including information from independent industry analysts and publications, as well as Datto's own estimates and research. Datto's estimates are derived from publicly available information released by third party sources, as well as data from its internal research, and are based on such data and Datto's knowledge of its industry, which Datto believes to be reasonable. The independent industry publications used in this presentation were not prepared on Datto's behalf. While Datto is not aware of any misstatements regarding any information in this presentation, forecasts, assumptions, expectations, beliefs, estimates and projects involve risk and uncertainties and are subject to change based on various factors. Non-GAAP Financial Measures This presentation contains the financial measures Non-GAAP Gross Profit, Non-GAAP Sales and Marketing Expense, Non-GAAP Research and Development Expense, Non-GAAP General and Administrative Expense, Adjusted EBITDA, Free Cash Flow, and related margins which are not recognized under generally accepted accounting principles in the United States ("GAAP"). Datto believes that non-GAAP financial information, when taken collectively, may be helpful to investors because it provides consistency and comparability with past financial performance and assists in comparisons with other companies, some of which use similar non-GAAP financial information to supplement their GAAP results. The non-GAAP financial information is presented for supplemental informational purposes only, and should not be considered a substitute for financial information presented in accordance with GAAP, and may be different from similarly-titled non-GAAP measures used by other companies. Non-GAAP Gross Profit, Non-GAAP Sales and Marketing Expense, Non-GAAP Research and Development Expense, Non-GAAP General and Administrative Expense, Adjusted EBITDA, Free Cash Flow and related margins have limitations as analytical tools, and you should not consider these measures either in isolation or as substitutes for other methods of analyzing the results as reported under GAAP. Reconciliation tables of the most directly comparable GAAP financial measures to the non-GAAP financial measures used can be found at the end of this presentation. datto 2#3Overview datto#4Datto -The MSP Cybersecurity Technology Company I Creator of Enterprise-Grade Technology for SMBs Mission critical software and cybersecurity solutions Integrated Platform for Managed Service Providers (MSPs) Largest pure-play MSP technology company Recurring Revenue SaaS Subscription Model 93% recurring revenue Enterprise-like financial metrics Secure, out of the box functionality designed for MSP delivery Platform to enable MSPs to grow and effectively serve SMB clients datto Metrics as of December 31, 2021 4#5Datto Overview 25 2,000+ 18,500+ Employees MSP Partners 2007 Founded in Norwalk, CT Global Locations $36Bn Current Global TAM1 93% $658M 28% FY 2021 Recurring Subscription Revenue ARR FY 2021 Adjusted EBITDA Margin Strong Growth at Scale Quarterly Subscription Revenue ($M) FY'21 19% YOY FY'20 $153 18% $147 $142 YOY $136 $129 $123 $116 $118 $111 $105 $100 $96 $90 $86 $81 $76 2018 2019 2020 2021 datto FY 2021 Metrics, ARR metric, global locations, employees and MSP Partners as of December 31, 2021. Adjusted EBITDA is presented on a non-GAAP basis. See appendix for reconciliation of Adjusted EBITDA to the most comparable GAAP financial measure. 1) Source: Frost & Sullivan. 5#6Our Guiding Principles $1 Always MSP Definable Technology Advantage Great Margin Opportunity Save MSPs Time datto Play the Long Game 6#7Investment Highlights 1 A Leading Platform of Purpose-Built MSP Software and Security Solutions 2 Targeting Massive and Underserved SMB IT Market at Inflection Point of MSP Adoption 3 Highly Differentiated Technology and Defensible MSP-Centric Approach datto 4 MSP Channel Enables Sales and Operating Leverage and Limits Churn datto 5 Predictable Subscription Revenue Model with Demonstrated Track Record of Profitability 6 Multiple Levers for Sustained Growth#8Recent Highlights Strong FY 2021 results • 19% yoy subscription revenue growth • Rule of 40 with adjusted EBTIDA margins in the low-to-mid-20% range Exceeded all targets in first full year as a public company Two significant product launches in H2 2021 SaaS Defense defends against unknown malware threats Datto Continuity for Microsoft Azure - everything MSPs love about BCDR now in the public cloud Acquired cybersecurity company Infocyte • Innovator in EDR and MDR cybersecurity technology Adds to the Company's rapidly expanding set of MSP-delivered security offerings. @ datto 8#9Datto's Leading Position in the MSP Market datto#10What is a Managed Service Provider (MSP)? Technology Experts 132,000+ providers of Outsourced IT services to Millions of SMBS around the world Mission-Critical IT Services Business Continuity Data Protection & Cybersecurity Networking & Connectivity Storage & Compute Infrastructure Software & Applications VOIP & Unified Communications Help Desk Services & Support SMBs Across Industries Law Firms Banks Hedge Funds State & Local Governments Hospitals & Healthcare Construction & Manufacturing Doctors & Dentists Real Estate Creative Agencies Schools & Universities Restaurants Consumer Retail ...And More datto 10#11SMBS are Overwhelmed by the Expanding Challenges of IT Management datto Lack Resources and Expertise Too Many Technology Choices Increased Regulatory Substantial Cost of Downtime Requirements Evolving Technologies Heightened Security Threats Difficulty of Optimizing Environment 11#12MSPs Provide the Critical Resources and Expertise SMBs Lack Technology Strategy datto Helpdesk Operations Purchasing 122 12#13Strong Secular Trends are Driving MSP Demand Digital Transformation Shift to Cloud Remote Work Tech Labor Shortage Cyber Attacks datto 13#14MSP Market Serving SMB Clients is Massive and Growing 132K MSPs Managing $193Bn Datto Global TAM: $36Bn datto +17.2% MSPs +13.4% Global SMB IT Spend: $1.3Tn + 4.5% SMBS datto Source: Frost & Sullivan, Market Intelligence Refresh on the Global TAM Assessment on the Managed Service Provider Market, 2021; Gartner, Forecast Analysis: Small-and-Midsize Business IT Spending, Worldwide 14#15Datto Helps MSPs Run Their Business From Top to Bottom datto MSP Pain Points Revenue Datto Purpose-Built Solutions Recurring revenue products for MSPs to "sell-through" Products that secure digital assets for SMB clients Sales and Marketing tools and support Datto Drives... Recurring Revenue DattoCon and MSP events for best practices Integrated Datto platform for MSPS Margin Superior product reliability Datto private cloud No published prices to SMBs Efficiency Profitable Margin Complete, turnkey solutions easy to deploy and manage remotely CRM, quoting, and invoicing business management software Scalable Operations • Training and certifications 15#16Datto's Differentiated Products & Technology datto#17Datto Creates Technology Purpose-Built for MSPs Exabyte Scale Private Cloud Cloud Native Management Platform Proprietary IP Two-Level Multi-Tenant Architecture Product Integrations Across Platform datto Open Ecosystem Integrations 17#18Datto's Integrated Product Platform @ Continuity SaaS Protection and SaaS Defense (User Security) Protects data and maximizes uptime, across public/private cloud workloads Protects cloud applications, prevents data loss and defends email against unknown malware threats M datto Remote Monitoring and Management (Endpoint Security) SaaS application for MSPs to protect and manage unlimited endpoints, with native ransomware detection Professional Services Automation (PSA) SaaS platform that centralizes business operations and workflows for MSPs 18#19Continuity Protects data and maximizes uptime, across public/private cloud workloads A PROTECT FILE SHARE SYNCHRONIZE RESTORE ADVANCED✓ CONFIGURE REPORTS 2998E219-19ED-4387-8845-47D v RESTORE FROM A BACKUP START A RESTORE Choose a System: - Local amsart-sql 172.20.10.3 amsart-file 172.20.10.7 AMSART-DC 172.20.10.1 AMSART-CRYPTO-1 122.20.10.81 amsart-centos-amsterdamartisans-local centos pfsense pfsense SE-MineCraft MinecraftTeam amsart-exch 172.20.10.2 AMSART-CRYPTO-2172.20.10. SMBShare SMBShare Choose a Recovery Type: File Restore Restore files and folders Volume Restore Restore volumels) to an SCSI target Local Virtualization Choose a Recovery Point: Select a recovery type in order to select a recovery point Beet the system in a local virtual environment datto Status Purchasing & Billing Admin MarketNow Partner Resources▼ Academy Support - Forum Bontech [INTERNAL D.... Virtualize in the Cloud Boot the system in the cloud Virtualize via Hypervisor Cloud Continuity Status Boot the system in a virtual environment Hide Overview ESX Upload Uploads a restore point to ESX host Bare Metal Restore Restore back to a physical or virtual system Export Image Export a recovery point as a VHD, VHDX VMDK, or VMDK-linked Overview SUBSCRIPTION 1 Year Term LICENSES PURCHASED 9999 LICENSES DEPLOYED 23 Month To Month 0 0 CREATE RMM TEMPLATE REGISTER AGENT LICENSES AVAILABLE 9976 0 Client Name Restore Agents Last Backup Last Screenshot The Grange G 2 6 months 13 hours. Last Ten Days 0000000000 Amsterdam Artisans ♡ 2 9day 13 hours 0000000000 Binary Backup 2 3 days 3 hours 0000000000 Blueberry Hill Labs Installation Pending Constant Constructions 1 10 minutes 1days 0000000000 Duff Brewery 2 1 2 hours 12 hours 0000000000 DVLB Ltd 进 2 1 hour 13 hours 0000000000 2 Superior continuity performance Ś Simple, predictable pricing model datto Replication to the secure Datto Cloud Unified management platform datto 19#20datto Status-> Purchasing & Billing Admin - MarketNow Partner Resources - Academy Support- Community Remember Me Account ▾ SaaS Protection & SaaS Defense Protects cloud applications, prevents data loss, and defends email against unknown malware threats SaaS Protection Status OVERVIEW LICENSES Client Name Product RM-Billing-ICR-1YR Office 365 Seats 12 Q Search REPORTING ADD SAAS PROTECTION CLIENT Backup Success Rate (24 hrs) SaaS Defense Status Details 100% Enabled RM-Billing-ICR-MTM Office 365 11 100% Enabled RM-Billing-TBR-MTM Office 365 13 100% Enabled RM-Discount-ICR-1YR-10-SPON... Office 365 1 100% Enabled > > datto RM-Discount-ICR-1YR-15-BOTH Office 365 13 100% Pending Authorization Check Authorization RM-Legacy-MTM-ICR-1 Office 365 11 100% Not Protected Activate SaaS Defense Test Client VI Office 365 0 Pending Authorization Not Protected Check Authorization 20 20#21AV Management Patch Management Application Management Encryption Control Continuity Integration Ransomware Detection M RMM SaaS application allowing MSPs to protect and manage unlimited endpoints, with native ransomware detection bontech Dashboards Big screen dashboard ^ Status, Alerts & Exceptions Status, Alerts & Except.. Sites Devices Filters and Groups Automation Policies Analytics Setup << < < < < < < +% Antivirus Status Running And U.. Recent Alerts datto Windows Patch Status No Policy No Data Not Running Not Detected Running An. Fully Patched Reboot Required Install Error Dark mode SHOW ME HOW SEND FEEDBACK + ADD A WIDGET Software Management Status No Bitlocker Cnabled Datto Continuity Backup Status Agent Paused Fallure O Warning Com 11 18 Non... Approved Pen. Reboot Required RESOLVE ⑦Holp 口 Created: Priority: Device: Category Message Site- Ticket 12 Provious Interface O about 3 hours ago RV3W3367 Event Log The required GPU resources could not All Handa Nauticat 120211124.0002 about 3 hours ago High ROW3307 Event Log The machine contains sondentical OP All Hands Neutical 12021126.0002 about 12 hours ago Critical WID-15-HV Ransomware 10 about 16 hours ago Moderate AZ-WINK-01 Component RANSOMWARE HAS BEEN DETECTED... Monitor Windows Experience State wit.. 72 - Binary Backup Amsterdam Artisans about 21 hours ago High RW3307 Event Log Shut down physical computer Stoppin All Hands Nautical T202124.0002 about 21 hours ago Moderate AZ AMSART 01 Component Reboot Required Monitor WINER.. Amsterdam Artisans 120211123.0013 Dotto Continuity about 22 hours ago Moderate AZ-AMSART 01 Component Stopped Auto-start Services Monitor Amsterdam Artisans 1 day ago High RYOW3367 Event Log The machine contains non identical GP All Hands Nautical 120291123.0003 NO 1 day ago High KV2307 Event Log The required GPU resources could not All Hands Nautic 120291123.0003 Success Windows 10 less than 20H2 121 Network Devices 13 O Server 21#22My Work Executive Sales Service Projects. RMM BCDR Financials + OPERATIONS▾ == Company Logo Opportunities this Month Top Opportunities Closing this Month: Open Ticket Summary Total Revenue- Quote 10336 $136,150.70 716 Created (last 10 400 Currently Open days) ABLE Manufacturing HQ Ok $112k 40k Administrator, Autotask datto BUSINESS MANAGEMENT Closed vs. Quota = Quote 10350 $106,600.92 Acme Inc 665 Completed (last 392 New Administrator, Autotask 10 days) NE Quote 10353 $18,625.00 ABLE Manufacturing HQ Administrator, Autotask First Response OK $430k 40k Forecasted 70.8 Met % (last 10) 45 Critical 1-10 of 41 Show All days) First Response Met (Last 7 Days) Active Projects by Line of Business PSA SaaS platform that centralizes business operations and workflows for MSPs including ticketing, project management, customer relationship management, quoting, procurement, invoicing, inventory management, and resource management. 150 50 datto Managed IT VoIP Managed IT Softw Managed IT Netwo Managed IT > IT Se Managed IT Consu Cloud Services>S 02/10/2022 02/11/2022 02/12/2022 02/13/2022 02/14/2022 02/15/2022 02/16/2022 Active Projects by % Complete (Hours) Survey Responses Revenue by Month Total: 352 137%-172% 102% 137% 66%-100% 34%-68% 100 200 300 400 $400k $300 Overall Hours Worked by Resource (This Week) Total: 14 150 100 50 Campbell Matzen, Shi Mayo, Nata Paterson, Sheridan, Zorica, Sa Worked Hours [140.04] Bilable Hours [127.57] Total: $917,971.39 Contracts up for Renewal Total: 14 Pending Revenue Jan 2022 6 Feb 2022 7 Mar 2022 1 $361k Apr 2022 0 $100k 0 4.67 Company 5 30k Nov 2021 Dec 2021 Jan 2022 ITEM DATE MONTH 22 22#23MSPs are in the Security Business and Datto is There With Them NIST Cybersecurity Framework Remote Monitoring & Management (RMM) Ransomware Detection for RMM Continuity IDENTIFY PROTECT ! DETECT RESPOND Ⓒ RECOVER datto SaaS Defense SaaS Protection 23#24The Power of Channel Leverage datto#25Datto Employs a Unique MSP-Centric Business Model Datto Solutions Datto Solutions Integrated Cloud-Native Platform Managed Services & Support datto MSP SMB datto $1 Recurring Revenue $ Recurring Revenue 25 25#26MSP-centric Model Solves the Challenges of Serving the SMB Market datto SALES LEVERAGE ww One Datto Sales Rep... Through Dozens ...Can Reach Thousands Of MSP Partners... Of SMB Customers datto datto CHURN PROTECTION If an MSP Loses an SMB, the MSP Can Migrate the Datto Stack to Another SMB Customer datto datto NATURAL REVENUE EXPANSION + + ARR from MSP Partners Naturally Expands As MSPs Add More Customers & Solutions SUPPORT & SERVICES LEVERAGE Aided by Datto Direct-to-Tech Support MSPs Provide Direct Support ww 26 26#27Uncapped Model With Multiple Vectors of Embedded Growth Acquisition Growth Retention MSPs X SMBS/MSP x Products/SMB x Units/Product x $/Unit = ARR 18.5K ARR/MSP $35.6K $658M Partner enablement: Penetrate existing SMBs and add new SMBs Add new partners in current markets Expand into new markets datto Values as of December 31, 2021 Cross Sell SMBS add employees, PCs, applications Upsell features and attach new products Partner Success & 24/7 Support Teams 27#28Datto Enables Our Partners To Be Effective Sellers of Datto Solutions MSP Enablement Resources Marketing Content for SMB Targeting Cultivating the MSP Ecosystem dattocon NOW a virtual experience DISCOVER datto MarketNow canalys 2020 Datto PARTNER SUMMIT ascii the ascii group inc. Training & Certifications Datto's Global State of the Channel Ransomware Report Sell-with Motion for Large Displacements MSP TECHNOLOGY Business Continuity September 16 DAY datto datto O Marketing Made MSPeasy The datto datto Datto's 2019 State of the MSP Report 00000 28#29MSP Partners Start Small and Grow With Datto Consistently Over Time ARR per MSP by Cohort $41,000 $35,600 Average .$32,000 $25,000 $20,000 $14,000 $8,000 $84,000 $75,000 $65,000 $58,000 Class of.... 2021 2020 2019 2018 2017 2016 2015 2014 2013 Pre-2013 datto Approximate Average as of December 31, 2021; Cohort ARR per MSP as of October 31, 2021 29#30Case Study: Mid Atlantic-based MSP ARR Evolution $300K $200K $100K $K 2010 2012 2014 First Continuity Purchase Land With Datto datto Standardize Across SMB Clients 2016 $300K ARR 2018 Platform Products Adopted ↓ First SaaS Protection Purchase First RMM Purchase First PSA Purchase ARR, or annual run-rate revenue, calculated as the monthly run-rate revenue for the last month of a period multiplied by 12; monthly run-rate revenue calculated by aggregating monthly subscription values during the final month of the reporting period from both long-term and month-to-month subscriptions Expand Across Datto Platform and Add Units 2020 30#31Strongest Value Proposition to MSPs Creates Deep Competitive Moats M datto datto Technology Secure, Reliable, Scalable, and All Cloud-Native Product Portfolio Broad and Integrated Turnkey Solutions With Unified Management Platform for MSPs ه6 Purpose-Built for MSPs Saves Them Time and Grows Their Revenues and Profits Complete MSP Focus Deepest Relationships, No Channel Conflict, No Published Prices to SMBs 31#32Financial Overview datto#33FY 2021 datto 19% Subscription Revenue Growth YoY 93% Recurring Revenue Growth and Profitability at Scale لاگ 28% Adj. EBITDA Margin 116% Dollar-Based Net Retention at 12/31/21 Positive Free Cash Flow datto Adjusted EBITDA and Free Cash Flow are non-GAAP metrics. See appendix for reconciliation of Adjusted EBITDA and Free Cash Flow to the most comparable GAAP financial measures.. 33#34Scalable SaaS Subscription Model $ SaaS Subscription Model Annual or multi-year subscriptions on initial term with auto-renewal Scaling with applications, users, and endpoints Typically billed monthly in advance $nl Scalable Unit Pricing Product Continuity SaaS Protection & Defense RMM & Ransomware Detection PSA Pricing Unit: Application Workloads @ SMB Users @ SMB Endpoints @ SMB Seats @ MSP datto 34#35Sustainable Revenue Growth at Scale Subscription Revenue ($M) 19% CAGR $142 $147 $153 $129 $136 $86 $90 $96 $100 $105 $111 $116 $118 $123 2018 2019 2020 2021 datto (2) Includes $41MM One-time Device, Professional Services & Other Revenue. Includes benefit from favorable foreign exchange rates of approximately 2%. $619M FY 2021 Total Revenue (1) 93% FY 2021 Revenue from Recurring Subscriptions 19% FY 2021 Subscription Revenue Growth YoY(2) 35#36Subscription Revenue Growth Has Been Accelerating Subscription Revenue Growth (% change YoY, constant currency) datto 22% 19% 2020 18% 17% 16% 15% 14% 2021 19% 36#37Strong Consistent Growth in ARR, MSP Partners and ARR per MSP Annual Run-Rate Revenue $MM $475 $543 $658 MSP Partners Number of Partners 18,500 17,000 16,600 ARR per MSP $ Thousands $29 $32 $36 Dec 2019 Dec 2020 Dec 2021 Dec 2019 Dec 2020 Dec 2021 Dec 2019 Dec 2020 Dec 2021 ARR, or annual run-rate revenue, calculated as the monthly run-rate revenue for the last month of a period multiplied by 12; monthly run-rate revenue calculated by aggregating monthly subscription values during the final month datto of the reporting period from both long-term and month-to-month subscriptions 37#38Powerful MSP-centric Model Delivers Consistent Cohort Growth Annual Cohort ARR* $ Thousands, Through December 31, 2021 Class of... ■2021 ■2020 -2019 116% -2018 Dollar-Based ■2017 Net Retention Rate 2016 (all products, a/o 12/31/21) 2015 7.5x ■ 2014 ARR Multiple 2013 For 2013 Cohort 2012 2011 2010 Dec-10 Dec-11 Dec-12 Dec-13 Dec-14 Dec-15 Dec-16 Dec-17 Dec-18 Dec-19 Dec-20 Dec-21 datto ARR, or annual run-rate revenue, calculated as the monthly run-rate revenue for the last month of a period multiplied by 12; monthly run-rate revenue calculated by aggregating monthly subscription values during the final month of the reporting period from both long-term and month-to-month subscriptions. *Includes Continuity, SaaS Protection and Networking products. Dollar-based net retention rate is calculated as ARR as of the last day of the current reporting period from partners with ARR as of the last day of the prior year comparative reporting period divided by ARR as of the last day of the prior year comparative reporting period.#39Strong Profitability Non-GAAP Gross Profit % Margin 74% 73% 67% FY 2019 FY 2020 FY 2021 Expanding Gross Margins datto Adjusted EBITDA % Margin 18% 29% 28% Free Cash Flow % Margin 13% 13% FY 2019 FY 2020 FY 2021 (6)% FY 2019 FY 2020 FY 2021 Strong Operating Leverage Improving Capital Efficiency Non-GAAP Gross Profit, Adjusted EBITDA and Free Cash Flow Margin are all non-GAAP metrics. See appendix for reconciliation of Non-GAAP Gross Profit, Adjusted EBITDA and Free Cash Flow to the most comparable GAAP financial measures. FY 2019, FY 2020, and FY 2021 refers to 12 months ending December 31, 2019, 2020 and 2021 respectively. 39#40Long-Term Target Financial Model Q4'2021 Target How We Get There Gross Margin % 72% ~75% . Lower product costs Subscription mix S&M % of Revenue 23% -20% • Optimize support Partner self-service Leverage from MSP channel model Innovation investment R&D % of Revenue 15% -15% · Security and cloud • Automation G&A % of Revenue 14% ~10% Operating leverage Adj. EBITDA Margin % 24% 30%+ CapEx % Revenue 9% ~5% Optimize cloud architecture Lower terabyte costs datto Non-GAAP Gross Margin, S&M % of Revenue, R&D % of Revenue, G&A % of Revenue and Adjusted EBITDA margin for Q4 2021 are all non-GAAP metrics. See appendix for reconciliation of Non-GAAP Gross Margin, S&M % of Revenue, R&D % of Revenue, G&A % of Revenue and Adjusted EBITDA margin to the most comparable GAAP financial measures.. 40#41Investment Highlights Recap 1 A Leading Platform of Purpose-Built MSP Software and Security Solutions 2 Targeting Massive and Underserved SMB IT Market at Inflection Point of MSP Adoption 3 Highly Differentiated Technology and Defensible MSP-Centric Approach datto 4 MSP Channel Enables Sales and Operating Leverage and Limits Churn datto 5 Predictable Subscription Revenue Model with Demonstrated Track Record of Profitability 6 Multiple Levers for Sustained Growth 41#42datto Appendix#43Non-GAAP Reconciliations $ thousands Net income (loss) Income tax Depreciation & amortization 2019 2020 2021 ($31,188) $22,498 $51,434 (2,511) 8,062 9,928 43,162 49.113 59,183 Interest and other expense, net 43,693 21,920 842 Loss on extinguishment of debt 19,231 8,488 Restructuring expense 3,835 Transaction related and other expense 3,112 5,153 Stock-based compensation expense 12,215 33,460 48,909 Adjusted EBITDA $84,602 $150,488 $175,449 $ thousands 2019 GAAP gross profit $301,445 2020 $368,581 2021 $442,309 Amortization of acquired intangible assets 4,700 5,023 9,451 Stock-based compensation expense 98 4,713 4,695 Restructuring expense 601 Non-GAAP Gross Profit $306,243 $378,918 $456,455 $ thousands 2019 2020 2021 GAAP net cash provided by operating activities $11,235 $108,698 $125,366 Less: Purchases of property and equipment (38,226) (40,466) (47,237) Free Cash Flow ($26,991) $68,232 $78,129 datto 43#44Non-GAAP Reconciliations (cont'd) $ thousands GAAP gross profit Amortization of acquired intangible assets Stock-based compensation expense Restructuring expense Non-GAAP gross profit Non-GAAP gross profit margin $ thousands GAAP sales and marketing expense Stock-based compensation expense Restructuring expense Non-GAAP sales and marketing expense $ thousands GAAP research and development expense Stock-based compensation expense Restructuring expense Non-GAAP research and development expense $ thousands GAAP general and administrative expense Stock-based compensation expense Restructuring expense Transaction related and other expense Non-GAAP general and administrative expense datto Q4 2021 $115,118 2,737 1,229 $119,084 72.5% Q4 2021 $40,023 (2,976) $37,047 Q4 2021 $31,209 (6,162) $25,047 Q4 2021 $27,570 (3,187) 1,016 $23,367 44