#1Investor Day Investor Day June 2021 © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. upwork#2Safe Harbor Investor Day June 2021 This presentation and the accompanying oral commentary contain "forward-looking" statements based on the beliefs and assumptions of Upwork Inc. (the "Company") and on information currently available to the Company. Forward-looking statements include all statements other than statements of historical fact contained in this presentation, including information or predictions concerning the future of the Company's business, anticipated events and trends, potential growth opportunities, competitive position, technological and market trends, industry environment, potential market opportunities, the economy and other future conditions. Any forward-looking statements made herein or made elsewhere by the Company are made solely based on information available to the Company as of the date hereof and based only on the Company's current beliefs, expectations and assumptions. As such, they are subject to inherent uncertainties, known and unknown risks and changes in circumstances that are difficult to predict and in many cases outside the Company's control, and you should not rely on such forward-looking statements. The Company makes no representation that the projected results will be achieved, and actual results may differ materially from the Company's expectations. Furthermore, the Company does not undertake any obligation to update or revise any forward-looking statements, to conform these statements to actual results or to make changes in the Company's expectations, except as required by law. In addition, any statements regarding the current and future impacts of the COVID-19 pandemic on our business and current and future impacts of actions we have taken in response to the COVID-19 pandemic are forward-looking statements and related to matters that are beyond our control and changing rapidly. Additional information regarding these and other risks and uncertainties that could cause actual results to differ materially from the Company's expectations is included under the caption "Risk Factors" in the Company's Quarterly Report on Form 10-Q for the three months ended March 31, 2021 filed with the Securities and Exchange Commission (the "SEC") on May 4, 2021 and the Company's other SEC filings. This presentation also contains estimates, forecasts and other statistical data made by independent parties and by the Company relating to market size and growth and other data about the Company's industry. This data involves a number of assumptions and limitations, and you are cautioned not to give undue weight to such estimates. In addition, projections, assumptions and estimates of the Company's future performance and the future performance of the markets in which the Company operates are necessarily subject to a high degree of uncertainty and risk. Moreover, neither the Company nor any other person makes any representation or warranty as to the accuracy or completeness of the information herein. This presentation is made solely for informational purposes. All third-party trademarks, including names, logos and brands, referenced by the Company in this presentation are property of their respective owners. All references to third-party trademarks are for identification purposes only and shall be considered nominative fair use under trademark law. In addition to the U.S. GAAP financials, this presentation includes certain non-GAAP financial measures. The non-GAAP measures have limitations as analytical tools, and you should not consider them in isolation or as a substitute for the most directly comparable financial measures prepared in accordance with U.S. GAAP. There are a number of limitations related to the use of these non-GAAP financial measures versus their nearest GAAP equivalents. Other companies, including companies in the Company's industry, may calculate non-GAAP financial measures differently or may use other measures to evaluate their performance, all of which could reduce the usefulness of non-GAAP financial measures as tools for comparison. The Company urges you to review the reconciliation of non-GAAP financial measures to the most directly comparable U.S. GAAP financial measures set forth in the Appendix, and not rely on any single financial measure to evaluate the Company's business. Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute.#3Welcome Hayden Brown Welcome June 2021 © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. upwork#4Work is rapidly evolving Welcome June 2021 © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. OLOURED 4#5Uniquely Positioned to Succeed U Massive TAM with secular tailwinds Largest work marketplace at scale ¹ H Deep and expanding competitive moats ¹ As measured by gross services volume (GSV). See appendix for the definition of gross services volume. Multiple growth opportunities Proven and experienced management team 5#6Our Mission Create economic opportunities so people have better lives. Welcome June 2021 © 2021 Upwork Inc. Proprietary and confidential. Do not distribute.#7Our Vision Independent talent at the heart of every business. Welcome June 2021 © 2021 Upwork Inc. Proprietary and confidential. Do not distribute.#8v) mm 20 A Win-Win Way to Work Companies • Narrow skill gaps • Accelerate agility and innovation • Prevent burnout Freelancers • Work on your own terms • Greater control over when and how you work, and whom you work with 8#9upwork C#10Freelancing Shows No Signs of Slowing Down Source: SIA Workforce Solutions Buyer Survey, 2020 Percent of Buyers Considering Online Staffing 5% 2015 47% 2020 10x growth 10#11Creating a Massive and Growing Opportunity ~225 Million Estimated number of global remote knowledge workers¹ X ~$5,850 Average freelancer GSV² 12021 estimate from Gartner - Forecast Analysis: Remote Workers Forecast, Worldwide August 2020. 2 TTM as of Dec. 31, 2020. || $1.3T Upwork Opportunity 11#12Cloud Stages of Adoption Customer Value Welcome 1 June 2021 2 Project AWS is evaluated and vetted on a project-by-project basis to solve specific needs on a one-off basis 3 © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. 4 Cloud Adoption Over Time Cloud-First The enterprise changes view from "why cloud?" to "why not cloud?" Hybrid AWS complements existing legacy systems and becomes an option for additional projects Scaling The enterprise makes investments to sustain long-term IT operations in the cloud 12#13Freelancer Stages of Adoption Customer Value Welcome 1 June 2021 2 Project Freelancers evaluated and vetted on a project-by-project basis to solve specific needs on a one-off basis 3 Freelancer Adoption Over Time Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. 4 Freelancer-First Companies change view from "why Upwork?" to "why not Upwork?" Hybrid Freelancers complement FTES and become an option for additional projects Scaling Companies make investments to leverage freelancers as core to the way they get work done 13#14Upwork Is the Most Comprehensive Work Marketplace Multiple ways to Upwork = the "always on" solution for companies hiring and managing freelancer programs at scale Welcome June 2021 © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. Talent Marketplace ™ Enterprise Suite Bring Your Own Talent Payroll Direct Contracts TM Project Catalog T Talent Scout ™ ...What's Next? upwork 14#15Featuring the Most Robust Community of Clients and Freelancers 10,000+ skills 1 73% of talent have college degrees ¹ 50+ categories with $10M+ in GSV ² ~40% of clients hired in multiple categories ² ~50% of Fortune 500 companies are clients ² ¹ February 2021 Upwork internally conducted survey. 2 Based on the trailing 12-month period ending March 31, 2021. VILL#16Our Business Model vs. "Gig" Companies Skills Control Relationship Economic Alignment Welcome June 2021 "Gig" Companies Workers are interchangeable and do not have specialized skills The platforms set the rates and algorithms play a bigger role in determining which worker works with which customer Workers tend to work in same geographic area as customers Company profits are extracted from service provider earnings, so platforms make more as providers make less 2021 Upwork Inc. Proprietary and confidential. Do not distribute. Upwork Highly skilled professionals; entrepreneurs building their own businesses Talent work on their own terms - choosing whom they work with, when they work, and how much to charge Clients and talent build relationships regardless of location Upwork benefits financially when talent charges higher rates, and thus does not encourage a race to the bottom 16#17Creating a Virtuous Cycle Value for Freelancers Find work quickly Access to quality, flexible projects from our global network Get paid on time Receive security and peace of mind with Upwork Payment Protection Build reputation Establish long-term credibility and relationships with roster of clients Growth opportunities Insights on in-demand skills and emerging areas Flexibility Expanding number of ways to Upwork Value for Clients Quality talent Global access to a verified Virtual Talent Bench™ across categories and price points Fast access to talent Receive proposals within minutes; 3 days average time to contract Cost-effective projects Take hiring budgets further with average 50% savings vs. hiring locally Work efficiently, effectively End-to-end suite of workflow tools Flexibility Expanding number of ways to Upwork Value for Upwork This engine results in: Highly sticky double opt-in platform with long-term relationships and recurring use, leading to increasing scale and recurring revenue More freelancers Increased GSV upwork More / bigger projects More skills / categories More clients Cross- selling#18Generating Abundant Growth Opportunities Expected horizon for significant value creation Near Term Brand Awareness Acquisition / Retention Enterprise Share of Wallet Product Line Diversification Opportunistic M&A Welcome June 2021 Mid Term Internationalization and Localization Talent Services Product Integrations Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. Long Term Take Rate Expansion 18#19Our Goal: 100% of businesses will have freelancers on their teams in the future Welcome June 2021 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. 19#20Our Winning Strategy 1 Innovating the work marketplace 2 Becoming a world-renowned brand 3 Augment SMB by winning the enterprise 4 5 Building an extraordinary hybrid team of employees and freelancers Investing aggressively for long-term value creation 20#21Product & Experience Sam Bright Product & Experience June 2021 © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. upwork#22Tectonic Change in the Way We Work Product & Experience June 2021 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. 22#23Remote Work Has Introduced a Transformative Moment Product & Experience June 2021 © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. LHALWERAD#24Hybrid Workforce Is the New M.O. Product & Experience June 2021 © 2021 Upwork Inc. Proprietary and confidential. Do not distribute.#25Disrupting Work Is the Next Innovation Frontier Product & Experience June 2021 © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. 2#26Upwork Is Innovating the Work Marketplace Transforming from a single product line company to a multi-product line company Product & Experience June 2021 © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. Talent Marketplace ™ Enterprise Suite Bring Your Own Talent Payroll Direct Contracts TM Project Catalog T Talent Scout ™ ...What's Next? upwork 26#27Product Strategic Priorities 1. Launch and Lead Our Work Marketplace 2. Scale Our Product Fundamentals 3. Drive Customer Growth 27#28ㅈ The world's work marketplace. Product & Experience June 2021 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute, upwork Lydia in Los Angeles, Rezanur in Mumbai. John in London, and in New York. Karen T. Illustrator Karolina upwork 5/5 Average Rating $150/hour 265 Jobs ope The world's work marketplace O VS 9. 28#29Where the World Wants to Work Product & Experience June 2021 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. 29#30All the Ways to Upwork Product & Experience TM upwork The world's work marketplace June 2021 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. Talent Marketplace™ Project Catalog™ Talent Scout™ Enterprise Suite™ 30#31Lilly D. Developer Let's get your product launch back on track."#32Our Product Priorities in Action Product & Experience June 2021 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. 32#33Launch and Lead Our Work Marketplace Direct Contracts Expanded offerings enabling freelancers to safely, securely, and easily invoice and bill non-Upwork clients for hourly work Product & Experience June 2021 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. upwork Find Talent Find Work Get Started Development & IT Design & Creative Sales & Marketing Writing & Translation Admin & Customer Support Finance & Accounting Fast, secure payments for projects outside Upwork Even if you didn't find your project through us, you can still use Upwork to manage contracts and get paid. Are you a client? View information here Why Upwork How it works Enterprise 1 Create a contract Your client accepts it Alexa Smith is requesting $500.00 For Graphic Design for Cleo from your client Jack Hammond. View Contract Send Request Log In You get paid quickly Sign Up#34Launch and Lead Our Work Marketplace Bring Your Own Talent Added features and capabilities to our Bring Your Own Talent solution to allow clients to onboard both Upwork and non-Upwork freelancers onto our platform for global unified billing, reporting, and overall contract management Product & Experience June 2021 Bring your own talent Track BYO invitations Recipient 8 Peter McCann Philip Campbell Bianca Swenson Juan Lindau Candace Laska David Shafer Celia Howes Type Invite & Contract Invite & Contract Invite & Contract Invite & Contract Invite & Contract Invite Only Invite Only Invite a Freelancer Status? Pending Sent Feb 9, 2021 Withdrawn Withdrawn Jan 1, 1970 Accepted Accepted Dec 7, 2020 Accepted Accepted Dec 7, 2020 Withdrawn Withdrawn Jan 1, 1970 Withdrawn Withdrawn Nov 19, 2020 Accepted Accepted Nov 9, 2020 Invite an Agency View Offer View Offer View Offer View Offer View Offer Hire Filters *** Ⓡ#35Launch and Lead Our Work Marketplace Project Catalog Project Catalog is a new product line that lets talent create productized, fixed-price projects and clients search, browse, and buy with just a few clicks Product & Experience June 2021 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. 2:53 E upwork Project Catalog™ Clear scope. Upfront price. No surprises. Dimitra D Complete your most pressing work with Project Catalog. Browse and buy predefined projects in just a few clicks. Brand Identity & Strategy upwork.com Try "video editing" or "data entry" 5 day delivery From $700 Sonny A *5.0 (213) E & CREATIVE Project Catalog Ardi D PLETE LOGO BRAND ALLEGEA A full brand identity design will motivate your target. 14 day delivery From $500 Shop by category that Stephanie D. *50 (29) Q Valeri B A guir bran#36Launch and Lead Our Work Marketplace Talent Scout Talent Scout is another new product line that offers hiring managers hands-on recruiting assistance without the expensive price tag of a traditional staffing agency Product & Experience June 2021 upwork Find Talent - Find Work Talent Scout Design & Creative Sales & Marketing Development & IT Why Upwork Enterprise Your ticket to the right talent Hire the Best Upwork recruiters can find you the right talent-people we've screened, tested, and know have the hard and soft skills you need. Looking for work? Log In Our recruiters put in the hiring hours so you don't have to Sifting through profiles, screening for skills, matching people to projects: finding the best independent talent takes time. With Talent Scout, you'll work with one Upwork recruiter who'll take care of all that, and help connect you to our top-tier of freelancers- people who care about doing the best work they Sign Up#372:56 E upwork upwork.com Find the best freelance jobs Watch a demo Browse jobs posted on Upwork, or jump right in and create a free profile to find the work that you love to do. Freelance Jobs Find Work Explore remote jobs Type of Work Try skills like "PHP" or "JavaScript" Any type of work Sign Up a Scale Our Product Fundamentals Search and Data Structure Continuous investments to improve search capabilities and underlying data structure to accommodate ever-expanding categories of work 37#38upwork Find Talent Find Work Why Upwork Enterprise About Us Our Leaders Careers Board of Directors Press Contact us Upwork Teams with Citrix to Power Flexible Work Resources Press Releases Next-generation solution pairs Citrix Workspace technology with best in class talent to fulfill immediate staffing demands, remote IT needs, and rigorous security requirements SANTA CLARA, Calif. - June 29, 2020-Upwork (NASDAQ: UPWK), the leading online talent solution, is teaming with Citrix Systems, Inc. (Nasdaq: CTXS), the global digital workspace leader, to power flexible work. Upwork today announced the launch of the Upwork Talent Solution with Citrix® Workspace"; a unique offering designed to deliver a best-in-class secure remote infrastructure for companies to boost efficiency and productivity as the world increasingly adopts the benefits of remote, on-demand talent. Research shows businesses are increasingly moving to more remote and 2:57 E upwork a Log In upwork.com Log In Sign Up Upwork and Citrix power secure remote work, together Upwork and Citrix: better together 1 Effective remote work Sign Up Upwork and Citrix have teamed up to bring more reliability and security to remote work engagements. As the world increasingly adopts the benefits of remote and on-demand talent, Upwork and Citrix have the solutions you need: the Upwork Talent Solution with Citrix Workspace and Upwork Microapps for Citrix Workspace. Efficiently integrate proven, remote talent with quick access to company tools and resources from anywhere and to any device. Security mone Scale Our Product Fundamentals Citrix Partnership with Citrix enables clients to simply and securely provision and deprovision Upwork talent onto corporate tools 38#39upwork Q Search Q Search All People & Rooms FAVORITES Favorite Messages PEOPLE T 8 Molly Sheehan Samantha Mazzeo View All People INTERVIEWS Matthew Strozak Test project sept 24 MS TO View All Interviews Insights Program Reporting Hiring Messages 20 Molly Sheehan 2:05 pm CDT Friendly Company [STD DEMO] a versation Zoom Meeting Up Upwork Call Phone Call Chat with Molly Sheehan! This room is private between the two of you. Say "Hi" to begin the conversation! 5 Al Scale Our Product Fundamentals Zoom Integration of Zoom video and voice communications onto the Upwork platform 39#40upwork Find Talent Find Work Why Upwork Enterprise Development & IT Design & Creative Sales & Marketing Writing & Translation Admin & Customer Support Finance & Accounting Upwork Payroll Upwork Payroll makes it easy to classify and pay your freelance team. So you can focus on growing your business and leave the admin hassle to us. Contact Us Q Manage and pay W-2 employees with Upwork Payroll Log In Sign Up Scale Our Product Fundamentals Payroll Integration Integration with iWorkGlobal significantly reduced onboarding time while providing transparency throughout the onboarding process 40#41Drive Customer Growth Connects Injected Connects to help talent get started, incentivize former talent to rejoin, and reward talent for submitting targeted proposals Product & Experience June 2021 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. 3:01 ||| Buy Connects 90 Your available Connects 10 for $1.50 upwork.com Select the amount to buy upwork Your account will be charged $1.50 100 Your new Connects balance will be 05/18/2022 These Connects will expire on#42Drive Customer Growth Diversity Badges Enable diverse talent to surface their certifications and help clients build more inclusive teams Product & Experience June 2021 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. upwork Filter By Q Search Talent Quality NEW TOP RATED PLUS TOP RATED RISING TALENT Where's Expert-Vetted? Diversity Certified Category All Categories Accounting Consulting Admin Support Customer Service Data Science Analytics Design & Creative Engineering & Architecture IT & Networking Legal Sales & Marketing Translation Web, Mobile & Software Dev Writing SEARCH Search MY HIRES Diversity certified X em... SAVED (13) Ben M. 17x Salesforce Certified Application Archite Des Moines, IA $120.00/hr $3k+ earned Experienced and Certified Salesforce professional av experience working with Salesforce and related syste Salesforce Sales Cloud Salesforce Service Cloud Clear filters Ethan W. CRM / Zapier Expert / Sales and Marketi South Lake..., CA $65.00/hr Automation and Workflow Expert Specializing in CR Intergromat Zaps and Automation Scenarios How ar Robyn O. Pipedrive API Mailchimp CRM 6 more 4 Jobs Talent Reports Messages 3 2:53 E upwork a upwork.com 4Minority-owned US Veteran-owned Verified ? Q 20 Canadian Aboriginal and Minority Supplier Council, National Minority Supplier Diversity Council (MBE) Verified Log In Veterans Affairs / Vetbiz, Veteran Owned Business Enterprise (VET) milk tak U.S. only LGBT-owned City of Louisville & Jefferson County, KY, Lesbian, Gay, Bisexual, Transgender Business Enterprise (LGBT) Verified .. Sign Up 10#43Drive Customer Growth SEO Strong improvements from consistent and systematic investments, including new content management system Product & Experience June 2021 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. graphic designer rates Rates charged by graphic designers on Upwork vary from $15 to $150 an hour, with an average rate of around $25 per hour. However, designers don't always bill hourly; it's also common for a designer or creative director to set a fixed price for the work, based on their understanding of your project requirements. https://www.upwork.com> hire graphic-designers › cost ⠀ Graphic Designer Hourly Rates | Cost to Hire... - Upwork People also ask How much should I charge as a graphic designer? How much do freelance graphic designers charge? X ↓ About featured snippets. a Feedback#44Drive Customer Growth SEM Expanded SEM presence on mobile, increased international reach, and improved bidding algorithms Product & Experience June 2021 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. 2:48 All .google.com Google freelance art director News Images Maps Videos Shopping Hire Now Ad https://www.upwork.com/ 27 Best Freelance Art Directors For Hire In May 2021 - Upwork™ Hire In-Demand, Remote Talent in 3 Easy Steps. Post a Job, Hire the Best, Secure Payments. It's Free to Post a Job and Get Qualified Proposals Within 24 Hours. View Top Talent Now! World's Work Marketplace. Increased Productivity. X Find Top Rated Agencies Talent Scout by Upwork Ad http://www.fiverr.com/#45Our Winning Strategy 1 Innovating the work marketplace 2 Becoming a world-renowned brand 3 Augment SMB by winning the enterprise 4 5 Building an extraordinary hybrid team of employees and freelancers Investing aggressively for long-term value creation 45#46Marketing Lars Asbjornsen Marketing June 2021 © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. upwork#47The Race to Win the $1.3T Work Marketplace Opportunity Platform-first service model Marketing fiverr. >Toptal. CATALANT Vettery indeed prime June 2021 Vetting & talent management Match & reputation Hybrid service model upwork Work Marketplace Platform & payments Payroll Shortlisting & success management © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. B2B marketing Sales Talent pool Traditional staffing service model "Platform when you want it - people when you don't." rh Robert Half Adeccu randstad Regional Staffing Cos Local Staffing Cos 47#48Addressing the Changing Needs of Staffing Customers A massive opportunity to capture market share • Changing customer needs: flexibility, transparency, control, and service • Lack of platform infrastructure and ecosystem • Operating model and scale tied to individual books of business, not the firm's • Transient talent pool vs. independent workers having chosen this as a career Marketing June 2021 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. R#49Work Marketplace Value Proposition Marketing 1 Enables companies and people to build powerful work relationships June 2021 2 Provides clients with access to a Virtual Talent Bench™ of trusted independent professionals Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. 3 Provides talent access to a virtual roster of trusted clients and quality opportunities 4 Enables businesses of any size to scale up or down based on demand and economic conditions 49#50Our Marketing Opportunity Marketing June 2021 1 COVID-19 has shattered "the fear of engaging remote talent" 3 Talent knows they don't have to live in an expensive city to get a great job 5 We aim to blur the lines between types of work that can be done by full-time employees and by independent talent Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. 2 Businesses know they can grow with distributed talent 4 Companies are realizing there is a competitive disadvantage to not have a robust strategy for using independent talent 6 We empower companies with the competitive advantage to scale up or down leveraging a Virtual Talent BenchTM on the Upwork work marketplace 50#51The Many Ways to Upwork - from "Gig to Big" Multiple ways to Upwork = the "always on" solution for companies hiring and managing freelancer programs at scale Marketing June 2021 © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. Talent Marketplace ™ Enterprise Suite Bring Your Own Talent Payroll Direct Contracts TM Project Catalog T Talent Scout ™ ...What's Next? upwork 51#52Hello, we're Upwork#53Accelerating Brand Awareness Redefined brand and PR messaging new value proposition to drive growth and awareness of what is possible on Upwork Marketing June 2021 $21M in 2021 to build brand awareness and drive overall demand Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. 56% YoY increase in brand media investment Laser focus on driving awareness among key personas in key categories, including tech, marketing / creative and customer service Vertically targeted brand advertising and media buys • Vertical content and PR strategies Strategic alliance partnerships • Vertical events, sponsorships Category influencer programs • Brand partnerships with major brands ● 53#54SEM Non-brand, SEO Non-brand Growth (2019-2020) FJP¹ Q1-2019 Q2-2019 ¹ See appendix for the definition of first job post (FJP). SEM overhaul began Q3-2019 Test Google tROAS non-brand SEM SEO optimization began Q4-2019 Test Google tROAS int'l + mobile SEM Q1-2020 All non-brand SEM TROAS Q2-2020 SEM Non-brand SEM broad match + new countries + proprietary bidding tool Q3-2020 SEO Non-brand Mobile + int'l expansion Q4-2020 54#55Infinite Personas and Categories Growth through depth Marketing со Tech & Product Lead Example: VP, Engineering ● Build and maintain my website June 2021 Build and maintain my mobile app Do QA testing on my product Augment or replace my internal UI/UX team Maintain a safe and secure dev environment for me Marketing & Creative Lead Example: VP, Marketing ● ● ● ● Augment my design staff Translate my marketing assets Build my new landing page Develop my campaign strategy Develop my social media strategy Execute my social media strategy Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. Growth through breadth Operations Lead Example: COO ● Recruit and manage my customer support operations Recruit and manage a skilled tech support team Let me outsource my accounting to a trusted accountant Provide me project-based accounting support 55#56Key Marketing and Acquisition Growth Levers for 2021 and Beyond Marketing 1 Launched our work marketplace marketing efforts to build awareness and drive demand June 2021 2 Expanding paid acquisition reach by: Expanding SEM keywords and mobile SEM conversion optimizations Growing international presence +40% YoY via keyword expansion globally Shifting to new brand messaging across channels to improve CTRS © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. 3 Improving conversion rates by: Matching intent to best product lines Improving CLTV model to optimize client keyword bidding 4 Automating and scaling SEM and social through proprietary bidding tool: Increasing registration-to-Start conversions through better client onboarding Aggressively supporting Enterprise Sales land and expand efforts Optimizing reactivation and retention efforts by moving to more holistic marketing automation 56#57Our Winning Strategy 1 Innovating the work marketplace 2 Building a world-renowned brand 3 Augment SMB by winning the enterprise 4 5 Building an extraordinary hybrid team of employees and freelancers Investing aggressively for long-term value creation 57#58Enterprise Sales Eric Gilpin Enterprise Sales June 2021 © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. upwork#59Building and Scaling Enterprise Sales Enterprise Sales 2016 Expanded sales team, opened Chicago office Hosted our 1st Work Without Limits Conference Surpassed 30K in Enterprise projects June 2021 2017 Launched Upwork Enterprise 2018 Launched Upwork Business Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. 2019 Signed 100th Enterprise client Launched partnership with Microsoft 2020 Sales restructure Accelerated growth 2021 59#60A Dynamic Platform to Help Enterprise Organizations Scale Multiple ways to Upwork = the "always on" solution for companies hiring and managing freelancer programs at scale Enterprise Sales June 2021 © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. Talent Marketplace ™ Enterprise Suite Bring Your Own Talent Payroll Direct Contracts TM Project Catalog T Talent Scout ™ ...What's Next? upwork 60#61A Dynamic Platform to Help Enterprise Organizations Scale Enterprise Suite Expert-Vetted Talent Bring Your Own Talent Custom Reporting Enterprise Billing Program Management Support Enterprise Sales June 2021 Global IC Classification Global Payroll Secure Onboarding Single Sign On Work Protection © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. Talent Marketplace ™ Enterprise Suite Bring Your Own Talent Payroll Direct Contracts TM Project Catalog T Talent Scout ™ ...What's Next? upwork 61#62The Power of Our Enterprise Offering Upwork Enterprise provides a powerful suite of contract management and compliance tools that help enterprise organizations work more strategically with remote freelancers, whether to support project-based work, staff augmentation, or build strategic teams of consultants Enterprise Sales June 2021 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. 130% 170 Enterprise client spend retention (Q1 2021) ~80 clients with over $1M spend (May 2021) avg. spending contracts per Enterprise client (Apr. 2020-Mar. 2021) ~20x the number of registered users per client compared to Marketplace (Apr. 2020-Mar. 2021)#63Traditional Models VS. Upwork Enterprise Source: ¹ North America Staffing Company Survey 2020 | Staffing Industry Analysts, 2020 22020 Staffing Industry NPSⓇ Benchmarks | ClearlyRated, 2020 3 Based on aggregated compensation data via multiple government sources compiled by EMSI Time-to-Fill Access to Quality Talent Cost of Hire The Old Way 16+ days¹ 40% fill rate, NPS score of 28² More operating costs, higher margins Upwork Enterprise 3 days 85% fill rate, NPS score of 60+ Fewer operating costs, more savings (avg. 30-50%) ³ Faster Hiring Greater Access to Quality Talent Meaningful Cost Savings Note: As of December 31, 2020. NPS is a measure of client and freelancer satisfaction on a scale ranging from negative 100 to 100 based on the standard question: "On a scale of 0 to 10, with 10 being extremely likely, how likely are you to recommend Upwork to a friend or colleague?" NPS is based on users that respond to the survey question after completing a project and users who respond to the survey question once every 60 days. NPS is calculated by using the standard methodology of subtracting the percentage of users that respond that they are not likely to recommend us from the percentage of users that respond that they are extremely likely to recommend us. 63#64Delivering Value for Enterprise Clients Microsoft Situation: Need for ways to effectively engage the freelance, or "on-demand," workforce Enterprise Sales June 2021 With Upwork In ~3 years, Microsoft completed ~10,000 projects on the Upwork platform, across 80 skill categories. 50% improvement in time-to-fill Extensive analysis proving compelling results in the form of increased speed to engage, quality of work, and cost savings#65How Microsoft Utilizes In-Demand Talent#66Delivering Value for Enterprise Clients insightsoftware Situation: Need to integrate, build, and service new technologies acquired through M&A in their product portfolio Enterprise Sales June 2021 With Upwork The team was able to access independent talent to support all of their individual product lines, enabling them to provide better service and support to their customers. 8x faster time-to-fill across the organization (90 days to 11 days) 4.9/5.0 $2.3M success ratings cost savings#67Delivering Value for Enterprise Clients Flexera Situation: Need a quick and efficient way to access talent with in-demand skills to support rapid growth Enterprise Sales June 2021 With Upwork Flexera implemented a corporate-wide initiative to work with more independent talent - using Upwork to fill certain skills in a matter of days versus months. 24x faster engagement with independent talent 2x faster project turnaround 1/2 the cost of traditional hiring sources#68Revenue from Enterprise Accounts Is Accelerating Enterprise Sales June 2021 Sales Enterprise Plan (Standard & Compliance) Revenue from Enterprise Accounts YOY Revenue Growth © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. 2020 $22.7M 44% Q1-2021 $7.8M 74% 68#69The Enterprise Opportunity Enterprise Sales June 2021 + Many more globally 51K 8K 1,600 200+ 250+ employee US-based companies assigned to sales teams (both inbound and outbound) Target ideal customer profile (ICP) accounts Target ICP customers with spend currently in the Marketplace Current Enterprise clients 1,000 accounts could deliver $1-2B in GSV 69#70Supported by a World-Class Enterprise Sales Organization Over 50 years Collective human capital leadership experience rh Robert Half AQUENT Linked in glassdoor vitamin CAREERBUILDERⓇ TEKsystems 70#71Built to Deliver Our Land and Expand Strategy Land . ● Expand Help clients expand their Upwork usage Increase customer satisfaction ● Acquire new accounts 18 current Account Executives . Enterprise Sales June 2021 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. Target AE Deal Productivity: 6+ deals/yr Sales Cycle: 3-6 months For every 15 reps, we could add $100M in future GSV per year#72The World's Best Companies Use Upwork to Transform Their Contingent Work Programs Microsoft (GE) GENESYS Digicel Enterprise Sales June 2021 AUTOMATTIC PGA OF SHIRT Nasdaq 5 PGA COREL airbnb GoDaddy BİSSELL® Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. ~50% of F500 companies are clients today 30% savings average savings frequently reported by businesses 3 days average time-to-fill#73Digicel Taps into a Global Freelance Network#74Our Winning Strategy 1 Innovating the work marketplace 2 Building a world-renowned team 3 Augment SMB by winning the enterprise 4 5 Building an extraordinary hybrid team of employees and freelancers Investing aggressively for long-term value creation 74#75Human Resources and Talent Innovation Zoë Harte Human Resources and Talent Innovation June 2021 © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. upwork#76Upwork's Winning Talent Strategy Human Resources and Talent Innovation 1 Extraordinary talent isn't restricted by geography June 2021 2 Extraordinary teams aren't homogenous © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. 3 Independent talent should be at the heart of every business, including ours 76#77Upwork Has Created a Culture with Freelancers at the Heart of Our Business Kunal P. Sydney Systems Analyst Jackson M. New York Web Designer Human Resources and Talent Innovation June 2021 3/4 of Upwork's workforce is made up of freelancers Diane R. Long Beach Product Manager Jessica L. Copenhagen QA Engineer Charles D. Toronto Project Manager Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. Camille A. Tempe Accountant 86 countries around the world with at least one freelance team member 100% of Upwork's departments are hybrid Ridhi A. Surat UX Designer Joseph M. Cordoba Video Producer Aika Y. San Francisco Computer Programmer 77#78Upwork on Upwork: How the Sales Operations team expands their potential with hybrid teams Benefit #1 Access to specialized skills Source: Internal company data 46% productivity increase 50% average project savings 78#79Upwork on Upwork: How the CX team drops biases and builds trust, leading to success that teams can measure and customers can feel Benefit #2 Strengthens our culture, including fostering greater diversity and inclusion Source: Internal company data 95% freelance composition 91 customer satisfaction (CSAT) score <5% attrition rate 81 Net Promoter Score (NPS) 79#80Upwork on Upwork: How Product & Engineering scales faster without compromising quality Benefit #3 Ability to scale teams up and down instantly Source: Internal company data 70+ agile development teams 350+ 24/7 remote developers coverage 3 mos time to launch Project Catalog™ 80#81Upwork on Upwork: How the Marketing team raises the bar on what's possible Benefit #4 Increased agility and innovation Source: Internal company data 900+ multichannel assets created in a quarter Creative directors Project managers Writers Motion designers Graphic designers UX designers UI designers Integrated producers Design directors 81#82Upwork on Upwork: How the Finance team improves work-life balance with independent accounting talent Benefit #5 Prevents burnout Source: Internal company data 24/7 coverage with remote talent 6-7 hrs less overtime per employee 5x faster time to engage 82#83Commitment to Strong ESG Practices Focus Area Environment Social Governance Initiatives ● ● Reducing emissions by limiting our physical corporate office footprint through our remote-first working model Reducing unnecessary commuting and travel Purchasing carbon offsets that promote environmental sustainability Building a more robust diversity, inclusion and belonging (DIBS) infrastructure Leveraging data to inform strategic talent process decisions • Preparing quantitative disclosures to demonstrate our progress on DIBS-related initiatives Evolving Board and governance practices to reflect our maturation as a public company Focusing on and responding to stockholder feedback Acting to protect and grow long-term stockholder value 1 As defined under California law AB 979, underrepresented communities includes certain racial, ethnic, and LGBT identities. Achievements to Date ✓ Enabled team members to avoid over 1 million commuting miles in 2019 ✓ Achieved carbon neutrality for 2019 and 2020 ✓ Committed to remaining carbon neutral going forward ✓ 50% of Board is female ✓ 3 of our 8 directors are from underrepresented communities¹ ✓ Implemented majority-vote standard for director elections and adopted proxy access ✓ The Board's Nominating and Governance Committee oversees all ESG functions 83#84Work is not a place. It's something you do. Human Resources and Talent Innovation June, 2021 © 2021 Upwork Inc. Proprietary and confidential. Do not distribute.#85Our Winning Strategy 1 Innovating the work marketplace 2 Building a world-renowned brand 3 Augment SMB by winning the enterprise 4 5 Building an extraordinary hybrid team of employees and freelancers Investing aggressively for long-term value creation 85#86Finance Jeff McCombs Finance June 2021 © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. upwork#87Four Reasons for Confidence Finance June 2021 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. 1. Strong financial foundation 2. Attractive business model resulting in strong client retention and high GSV predictability 3. Strong client demand 4. Compelling margin structure#881. Strong Financial Foundation#89Strong Financial Foundation EBITDA ($M) 15.0 10.0 5.0 0.0 Finance 3.8 7.4 FY2018 FY2019 June 2021 14.0 6.9 FY2020 Q1-2021 Cash and Marketable Securities ($M) 200.0 150.0 100.0 50.0 0.0 129.1 FY2018 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. 133.9 169.7 169.8 FY2019 FY2020 Q1-2021 Debt ($M) 25.0 20.0 15.0 10.0 5.0 0.0 23.9 111 18.3 FY2018 FY2019 10.7 8.8 FY2020 Q1-2021 89#902. Attractive Business Model with Strong Client Retention#91Three Talent Plans Finance 1 Freelancer Basic • Access to quality projects • Quickly apply and get hired • Get paid securely and on time June 2021 2 Freelancer Plus Includes all Freelancer Basic features + • Customized profile URL • Insight into competitor bid ranges • Monthly Connects package* *not included in Agency Plus © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. 3 Agency Plus Includes all Freelancer Plus features + • Unlimited team members • Shared Connects functionality 91#92Talent Plans Subscription Cost Freelancer Service Fee Finance June 20211 Freelancer Basic No subscription 20%/10% / 5% Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. Freelancer Plus $15/mo 20%/10% / 5% Agency Plus $20 / mo 20%/10% / 5% 92#93Four Client Plans Finance 1 Basic • Access to a global talent pool • • Payment protection plan • Customer support Safe and easy payments June 2021 2 Plus Includes all Basic features + • Invites to talent • Featured Jobs upgrade • Connects package • Recruiting services © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. 3 Enterprise: Standard Includes all Plus features + • Custom reporting • API access • Expert-vetted talent pools and talent clouds • SSO / permissions • Purchase order management ● Consolidated invoicing and billing 4 Enterprise: Compliance Includes all Enterprise: Standard features + • Compliance services • Worker classification Misclassification indemnification • Work protection program 93#94Client Plans Subscription Cost Client Fee Freelancer Service Fee Finance June 20211 Basic No subscription 3% 20%/10% / 5% Plus $49.99 / mo 0%-3% 20%/10% / 5% Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. Enterprise: Enterprise: Standard Compliance $1,500 / mo 15% 10% $3,000 / mo 30% 10% 94#95Client Spend Retention Rates Are Compelling and Accelerating Client Spend Retention (¹) 110% 105% 100% 95% 103% Q1-2018 106% 108% Q2-2018 Q3-2018 Note: (1) See appendix for the definition of client spend retention. 108% 107% Q4-2018 Q1-2019 105% Q2-2019 104% Q3-2019 102% Q4-2019 102% 100% Q1-2020 Q2-2020 100% Q3-2020 102% Q4-2020 106% Q1-2021 109% April-2021 95#96Strong Client Spend Retention Provides High GSV Predictability Note: (1) See appendix for the definition of client cohort. GSV GSV by Annual Client Cohort(1) Before 2016 $2.5B $2.0B $1.5B $1.0B $500M $200M $1.15B 2016 2016 2017 $1.37B 2017 2018 $1.76B 2018 2019 2020 $2.09B 2019 $2.52B 2020 96#97GSV Acceleration Among Newly Acquired Clients Finance June 2021 GSV GSV from Clients Acquired in Year 2016 10% 2017 16% 2018 6% 2019 37% 2020 YOY Growth 97#98Strong Client Spend Retention Provides High GSV Predictability GSV Q1-2019 Q2-2019 Q3-2019 Q4-2019 Q1-2020 Q2-2020 GSV by Quarterly Client Cohort Q1-2019 Q1-2020 Q1-2021 Q3-2020 Q2-2019 Q2-2020 Q4-2020 Q3-2019 Q3-2020 Q1-2021 Q4-2019 Q4-2020 98#99Spend from Clients Acquired in the Quarter Has Accelerated GSV from Clients Acquired in Quarter GSV 6% Q1-2019 11% Q2-2019 5% Q3-2019 3% Q4-2019 2% Q1-2020 30% Q2-2020 47% Q3-2020 61% Q4-2020 73% Q1-2021 Yo Y Growth 99#100Client Behavior Changed, Starting in Q2-2020 Since Q2-2020... Finance June 2021 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. Older Cohorts Are Increasing Spend 105% ~5pt Average QoQ cohort spend retention (¹) from cohorts aged 1+ years in each of the past 3 quarters Notes: (1) Referencing quarterly cohorts. See appendix for the definition of cohort spend retention. Newer Cohorts Are Growing Faster 102% lift over historical average ~10pt Average QoQ cohort spend retention from start period to 2nd period for Q2-2020 to Q4-2020 cohorts lift over historical average#101It's a profound moment when you realize there is a freelancer somewhere in the world who can make whatever you're dreaming up a reality; it fundamentally changes how you work and makes the impossible possible. Kevin Scott, head of technology, PGA of America Finance June 2021 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. 101#1023. Strong Client Demand#103Client Demand Is Fueling Accelerated Top-Line Growth Finance June 2021 GSV YOY Growth $800M $700M $600M $500M $400M $300M $200M $100M $M $560M 15% Q1-2020 GSV $582M 12% Q2-2020 $655M 23% Q3-2020 $728M 33% Q4-2020 $787M 41% Q1-2021 50% 45% 40% 35% 30% 25% 20% 15% 10% 5% 0% YOY Growth 103#104GSV Acceleration Has Been Driven by Growth in Active Clients TTM Active Clients (1) 700K 600K 500K 400K 300K 200K 100K OK 10% Q1-2019 10% Q2-2019 Note: (1) See appendix for the definition of active clients. 10% Q3-2019 9% Q4-2019 7% Q1-2020 9% Q2-2020 Active client count growth has accelerated for 4 consecutive quarters 12% Q3-2020 17% YoY Growth Q4-2020 25% Q1-2021 TTM Active Clients 25% 20% 15% 10% 5% 0% YOY Growth 104#105GSV Per Active Client Is Increasing GSV $4,000 $3,750 $3,500 $3,250 $3,000 10% 7% Q1-2019 9% 5% Q2-2019 8% Note: (1) See appendix for the definition of GSV per active client. 2% Q3-2019 7% 1% Q4-2019 7% 5% Q1-2020 4% 2% Q2-2020 TTM Avg GSV / Active Client(¹) *Acquired clients are defined as active clients who started on Upwork in the trailing 12-month period. 5% *Retained clients are defined as active clients who didn't start on Upwork in the trailing 12-month period. 3% Q3-2020 9% YOY Avg GSV / Retained Client 7% Q4-2020 11% YOY Avg GSV / Acquired Client 9% Q1-2021 15% 10% 5% 0% YOY Growth 105#106Our Large Base of Core Clients Is Also Driving GSV Growth >80% of GSV on our platform comes from core clients, (1) which represent >20% of total clients(2) Notes: (1) See appendix for the definition of core clients. (2) As of 2021. Core Clients (Thousands) Core Clients (1) & YoY Growth 150 125 100 75 50 25 0 77 3% 2016 86 13% 2017 106 22% 2018 124 18% 2019 145 17% 2020 152 18% Q1-2021 50% 45% 40% 35% 30% 25% 20% 15% 10% 5% 0% YOY Growth 106#107We Are Adding High-Value Clients at an Accelerating Pace Note: (1) See appendix for the definition of high-value clients. High-Value Clients (¹) 3,500 3,000 2,500 2,000 1,500 1,000 500 0 Number of Clients with GSV Exceeding $100K During the Trailing 12 Months ~1,200 25% 2016 ~1,500 27% 2017 -2,100 41% 2018 ~2,600 22% 2019 3,100+ 23% 2020 3,400+ 27% Q1-2021 100% 90% 80% 70% 60% 50% 40% 30% 20% 10% 0% YOY Growth 107#108Majority of Client Growth Is Organic and We Are Growing Performance Marketing Quickly New Clients 27% 3% Q1-2019 - 35% 4% Q2-2019 26% 0% Q3-2019 19% -4% Q4-2019 10% -7% Q1-2020 31% 19% Q2-2020 Performance Marketing YOY Growth 72% 35% Q3-2020 Organic / Other YOY Growth 85% 39% Q4-2020 Clients from Performance Marketing 111% 56% Q1-2021 Clients from Organic / Other 150% 125% 100% 75% 50% 25% 0% -25% YOY Growth 108#109We Have Grown Our Marketing Investments Significantly While Materially Improving Efficiency Total Marketing Spend 34% 2018 35% 2019 37% 2020 50% 2021-Q1 YOY Growth Total Marketing Spend 80% 60% 40% 20% 0% YOY Growth 109#110Our Investment Approach Is Rooted in EVA Finance June 2021 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. Economic Value Added (EVA) • Maximize investment wherever return is >WACC Driving growth within this constraint is top priority ● EBITDA margin is important, but secondary Details 5-year revenue attribution window Payback period is a consideration ● ● ● Given strong retention curves, target LTV:CAC averages ~3x 110#111Illustrative Unit Economics per Acquired Client Performance Marketing ~$7K ~80% 5-year spend Contribution margin Finance Y1 Y2 June 2021 Y3 >25% Target IRR Y4 Y5 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. Sales ~$4M 5-year spend Y1 Cumulative Revenue ($) ~50% Contribution margin Y2 Y3 Cumulative Contribution Margin ($) >25% Target IRR Y4 Y5 111#112Long-Term Target Growth Rates of 20%+ Finance June 2021 Marketplace Managed Services Active TTM Clients GSV per Active TTM Client GSV Take Rate Revenue GSV and Revenue Long-Term Target YoY Growth Rates 10-20% 0-10% 20%+ >0% 20%++ -10% TTM YOY Growth Rates (as of Q1-2021) 25% 2% 27% 1% 28% 10% 112#113Leading to Target Revenue of $1B+ in 2025 Finance June 2021 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. 113#1144. Compelling Margin Structure#115Our Compelling Margin Structure High and expanding gross margins Industry-leading investment levels in R&D to extend competitive moats Opportunities for leverage in R&D and G&A Will invest aggressively in sales and marketing to drive growth and maximize economic value added Notes: (1) Marketplace gross margin is defined as total gross profit, excluding revenue from Managed Services and cost of freelancer services to deliver Managed Services, divided by Marketplace revenue. (2) Managed Services gross margin is defined as Managed Services revenue less cost of freelancer services to deliver Managed Services, divided by Managed Services revenue. Numbers are non-GAAP. Non-GAAP here excludes SBC, amortization, and non-cash charitable donations. All numbers reflect depreciation expense, except for EBITDA. % of Revenue Marketplace Gross Margin ¹ Managed Services Gross Margin 2 Total Gross Margin R&D S&M G&A Transaction Losses EBITDA FY2018 75% 17% 68% 21% 28% 16% 2% 1% FY2019 77% 17% 71% 19% 31% 18% 1% 2% FY2020 78% 19% 72% 20% 34% 15% 1% 4% Q1-2021 78% 19% 73% 21% 34% 14% 1% 6% LT Target 80-85% 20% 80-85% 15-20% 20-25% 8-10% 1-2% 30-35% 115#116Significant opportunity for sustainable, long-term growth with attractive margins Finance June 2021 © 2021 Upwork Inc. Proprietary and confidential. Do not distribute.#117Uniquely Positioned to Succeed U Massive TAM with secular tailwinds ¹ As measured by GSV Largest work marketplace at scale ¹ H Deep and expanding competitive moats Multiple growth opportunities Proven and experienced management team 117#118Appendix Appendix June 2021 © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. upwork#119Key Metric Definitions Appendix June 2021 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. Active Clients A client who has had spend activity during the trailing 12-month period is considered active. Client Cohort A client belongs to an annual or quarterly cohort, as the case may be, based on the date of first spend activity with a freelancer. Client Spend Retention Client spend retention is calculated by dividing our recurring client spend by our base client spend. We define base client spend as the aggregate client spend from all clients during the four quarters ended one year prior to the date of measurement. We define our recurring client spend as the aggregate client spend during the four quarters ended on the date of measurement from the same clients included in our measure of base client spend. Core Clients A core client is defined as a client that has spent in the aggregate at least $5,000 since beginning to use our platform and also had spend activity during the 12 months preceding the date of measurement. 119#120Key Metric Definitions Appendix June 2021 Ⓒ2021 Upwork Inc. Proprietary and confidential. Do not distribute. First Job Post (FJP) The first job a client posts on our platform. Gross Services Volume (GSV) Gross services volume, or GSV, includes both client spend and additional fees charged for other services. GSV per Active Client GSV per active client is calculated by dividing total trailing 12-month GSV by the number of active clients at the date of measurement. High-Value Clients A high-value client is one who has a minimum total GSV of $100K in the trailing 12-month period. QoQ Cohort Spend Retention QoQ cohort spend retention is calculated by dividing retention period spend by base period spend for any given client cohort, where retention period spend represents the aggregate spend by the client cohort during the quarter of measurement and the base period spend represents the aggregate spend by the same client cohort during the quarter immediately preceding the quarter of measurement. 120#121Summary of Changes to Our Publicly Disclosed Metrics Appendix June 2021 © 2021 Upwork Inc. Proprietary and confidential. Do not distribute. Metric Client spend retention Core clients TTM active clients TTM GSV per active client Annual cohort performance Quarterly cohort performance High-value clients Timing Deprecating after Q2-2021 Deprecating after Q2-2021 Quarterly disclosure starting Q2-2021 Quarterly disclosure starting Q2-2021 Annual disclosure starting Q4-2021 One-time disclosure One-time disclosure 121#122GAAP to Non-GAAP Reconciliation GAAP Marketplace COR Stock-based compensation Non-GAAP Marketplace COR Non-GAAP Marketplace Gross Margin (%) GAAP Managed Services COR Non-GAAP Managed Services COR Non-GAAP Managed Service Gross Margin (%) GAAP COR Stock-based compensation Non-GAAP Total COR Non-GAAP Total Gross Margin (%) FY2018 FY2019 FY2020 Q1-2021 FY2018 57.0 -0.3 56.7 75% 24.5 24.5 17% 81.5 -0.3 81.2 68% 61.4 -0.5 60.9 77% 26.8 26.8 17% 88.1 -0.5 87.7 $Millions 71% 75.6 -0.8 74.8 78% 28.7 28.7 19% 104.3 -0.8 103.5 72% 23.2 -0.2 23.0 78% 7.2 7.2 19% 30.4 -0.2 30.2 73% 25% 0% 25% 83% 83% 32% 0% 32% % of Related Revenue FY2019 FY2020 Q1-2021 23% 0% 23% 83% 83% 29% 0% 29% 22% 0% 22% 81% 81% 28% 0% 28% Notes: (1) Figures have been rounded. (2) Marketplace gross margin is using Marketplace revenue and total COR less Managed Services COR. (3) Managed Services gross margin is using Managed Services revenue and Managed Services COR. 22% 0% 22% 81% 81% 27% 0% 27% 122#123GAAP to Non-GAAP Reconciliation GAAP R&D Stock-based compensation Non-GAAP R&D GAAP S&M Stock-based compensation Non-GAAP S&M GAAP G&A Stock-based compensation Amortization Non-cash charitable Non-GAAP G&A Notes: (1) Figures have been rounded. FY2018 FY2019 FY2020 55.5 -3.3 52.2 73.0 -1.6 71.3 49.3 -5.2 -2.7 -0.2 41.3 64.0 -6.5 57.6 95.9 -2.6 93.3 67.3 -9.3 -2.7 -0.7 $Millions 54.7 83.5 -9.8 73.7 133.2 -4.4 128.8 71.5 -10.5 -2.7 -0.8 57.6 Q1-2021 FY2018 26.6 -3.3 23.3 39.6 -1.3 38.3 23.5 -6.4 -0.7 -0.2 16.2 22% -1% 21% 29% -1% 28% 19% -2% -1% 0% 16% % of Related Revenue FY2019 FY2020 21% -2% 19% 32% -1 31% 22% -3% -1% 0% 18% 22% -3% 20% 36% -1% 34% 19% -3% -1% 0% 15% Q1-2021 23% -3% 21% 35% -1% 34% 21% -6% -1% 0% 14% 123