Dear Shareholders As we close the third quarter of 2022, Upwork has clear indicators that both our business and our value proposition continue to be critical to customers in times of economic uncertainty. Revenue grew 24% year-over-year to $158.6 million, Gross Services Volume (GSV) grew 14% year-over-year to exceed $11 billion in the quarter once again, GAAP net loss was $(24.8) million, and adjusted EBITDA was $(2.9) million. We are focused on making prudent and sustainable investments in our business to drive steady, durable growth, even against a backdrop of challenging macroeconomic conditions. Importantly, our customers continue to count on us to enable their critical work and their businesses during these uncertain times. Upwork has both pioneered and benefited from the major paradigm shifts around remote work and hybrid workforces—fundamental changes that have shaped the new reality of work as we know it today. This sea change is illustrated by the fact that one-fourth of American workers are now working remote-first or mostly remote, while 71% of companies expect remote work to be part of their standard operations moving forward . This new work reality opens up a2 vast opportunity for Upwork to introduce ourselves to the 90% or more of companies and hiring managers who have not been aware of or considered Upwork and to bring them into the fold as customers. Nowhere has that opportunity been more apparent and central to our priorities than the late-September launch of our new brand campaign, “This Is How We Work Now.” Appearing across TV, online video, streaming audio, digital, and social media, the campaign reinforces Upwork’s belief that work should unleash human potential instead of limit it and emphasizes that now is the time to embrace the new ways of working that have emerged over the past few years. It targets mainstream prospects—clients and talent alike—who largely aren’t yet aware of Upwork but, like us, recognize that the world of work has changed forever. Our strong business position and resonant value proposition allow us to remain on offense, evident through both our new brand campaign as well as our amplification of benefits most valuable to our clients: flexibility in hiring, expert talent at their fingertips, operational agility, and bottom-line savings. Our solution satisfies the tight budgets that many organizations are implementing amid economic uncertainty—clients find that they can realize cost savings upwards of 50% by using Upwork compared with traditional staffing alternatives. By delivering highly skilled, diverse talent from more than 180 countries affordably and quickly, clients can have greater flexibility with their cost structure and reduce operating costs through talent innovation. As a result, we are helping companies improve their EBITDA and generate value-added growth while maintaining the optionality that has been shown by McKinsey to be vitally important in weathering—or even accelerating during—economic downturns. Notable brands that we welcomed as Enterprise Clients in the quarter include Anheuser-Busch InBev (AB InBev), Constellation Brands, Cushman & Wakefield, iCIMS, and Marriott International. These companies are leveraging our platform to deliver on their business plans; tap new sources of scalable, flexible remote talent; and retain a competitive advantage. 2 According to Upwork Future Workforce Report 2022 data. 1 GSV represents the total amount that clients spend on both our marketplace offerings and our managed services offering as well as additional fees we charge to talent for services. 2

Market makers like these new customers contributed to Enterprise Revenue growing a healthy 41% year-over-year to $12.5 million in the third quarter. Coupled with continued strong growth of clients spending $1 million or more, this underscores how our value proposition resonates with Enterprise Clients. We continue to invest in innovating the work marketplace with the goal of helping clients and talent start work more easily on the Upwork platform and return to Upwork time after time for a consistent and productive experience. Upwork delivers critical and differentiated value not just in matching clients and talent, but also in serving as the hub for seamless “back office” tasks for talent around invoicing and getting paid and, equally, contract management and payment activities for clients. We enhanced these core experiences in the third quarter, debuting improvements to our Contract Workroom that reduce friction and allow clients and talent to manage contracts, navigate all their contract actions, and more easily review weekly billings, earnings, contract terms, and feedback. Additionally, we made enhancements to our Enterprise Suite by enabling multi-approver, team-based approvals that support large-scale and complex workflows and adding more refined search functionality for faster access to our global pool of Expert-Vetted Talent who are ready and pre-approved to work with these companies. Project CatalogTM Consultations—made available across all 90+ categories of work during the third quarter—continue to drive effective connections and collaboration between clients and talent. Enhancements this quarter improve the experience, allowing them to confirm scope, skills required, feasibility, and timeline for a potential project, driving speed in starting work together, which can be 50% faster than on Talent Marketplace. These enhancements also enable customers to establish longer-term relationships that go beyond an initial project engagement. Ultimately, this drives elevated client spend on Project Catalog. In fact, 30-day spend by customers who use Consultations is nearly three times what customers who only purchase on Project Catalog spend. Lastly, thousands of talented professionals on our marketplace are adding profile badges that display and validate their expertise through our budding partnership with Credly, the market leader in digital workforce credentialing, enabling talent and clients to match faster and with more confidence. Equipped with access to a vast supply of talent and job posts and the technological capabilities to engage more effectively and efficiently, clients and talent are together defining the new reality of work, blazing the trail regardless of the economic uncertainty that may persist. To be sure, as we expected since our second-quarter earnings, our customers are not fully immune to that uncertainty, evidenced by the softness we continue to see in some metrics. Nonetheless, revenue impact in the third quarter from these conditions was in line with our previously-shared expectations. We have seen the softer client acquisition and retention trends that we observed in the second quarter stabilize in the third quarter, with the softness continuing to be more pronounced in Europe and with small- and medium-sized businesses. Our Enterprise Land team also saw elongated sales cycles due to the macroeconomic outlook for a handful of accounts. This, plus some operational growing pains, resulted in fewer Enterprise Clients signed in the third quarter than targeted. We are remedying the operational growing pains and believe the Enterprise opportunity remains as attractive as ever for Upwork. Additionally, we continue to manage our own business with discipline. Being prudent with resources has always been a guiding principle at Upwork, and as the economic outlook evolves, we have several measures underway, including evaluating budgets; adjusting hiring timing and prioritizing roles more aggressively; reviewing and reducing vendor spend; and ensuring we have a tight operating cadence around cost management with a high degree of visibility and internal partnership toward our goals. Due to the largely recurring and programmatic nature of the majority of customer activity on our platform, we are able to monitor for changes in behavior as they occur and be nimble in making adjustments to our plans as needed. This gives us further confidence in our ability to 3

manage the business responsibly through a dynamic environment. We still view this period of macroeconomic uncertainty as a critical time for us to be focused on expanding our position as a market leader and cementing new, integral ways of working across the work ecosystem. We see businesses continuing to turn to Upwork as the always-on source for highly skilled remote workers, regardless of their industry, whether their business need is project-based or ongoing, where they stand in their workforce transformation, or the current economic climate. We also know that Upwork fosters a deep, diverse, and highly skilled talent community across the globe. The world’s work marketplace remains the center of gravity for these work and career innovators to build trusted, lasting relationships and get more done together, and we will continue to innovate, evangelize, and scale it in the fourth quarter and beyond. 4

Q3’22 Business Highlights Innovating the Work Marketplace In the third quarter we continued to innovate the work marketplace and execute against our three-pronged product strategy of: 1) making it easy for clients and talent to get started on the Upwork platform, 2) ensuring they have a delightful experience when completing their first job, and 3) establishing Upwork as the place clients and talent come back to again and again for work. We redesigned the Contract Workroom to make it easier for all Upwork users to manage their work agreements. All transactions on the platform will now use this Contract Workroom. When customers now click on an active contract, they will see a refreshed user interface that will help them easily navigate all their contract actions; find their recent files, weekly billings, and earnings; and easily surface their contract terms and feedback, allowing for a much more seamless and streamlined experience. As mentioned earlier, talent on our marketplace have the ability to add profile badges that display and validate their expertise through our partnership with Credly. Credly works with leading organizations that share our focus on unleashing the potential of the workforce via digital credentials. This partnership allows talent to import their Credly certification badges into their Upwork profile, giving them more credibility when clients seek out certain skill sets, as well as enables talent and clients to connect faster and with more confidence. On the heels of Consultations and Project Tiers (that give talent the ability to add a custom title or description to each “tier” of service they offer), Career Innovator: Kate L. Harrison With a bachelor’s degree from Vassar College, a master’s degree from Yale, and a law degree from Pace Law School, Expert-Vetted marketing strategist Kate L. Harrison has a storied career, deep expertise, and unlimited opportunities. Yet Upwork is her favorite place to meet and work with new clients. “I was working with nonprofits and tech companies, doing work I love, but everything was very local,” Kate said. “I saw the opportunity to freelance on Upwork, and it immediately provided me with access to interesting clients all around the country exactly at the moment when they are actively looking for support.” Today, Kate works with a mix of Fortune 500 clients, leading nonprofits, and tech startups through the platform. “I never have to pay for Google Ads. I don’t drive traffic to my website. I just point people to my Upwork profile. It’s great!” she noted. “Another benefit of Upwork is that it has helped me build my own talent bench of specialists who I can bring in as needed to help support my clients. My clients love the end-to-end branding and marketing services we are able to provide—usually at a fraction of the cost of doing things in-house. “A lot of my Upwork project clients turn into long-term relationships. We all love the easy billing and tracking that is baked into the system. The platform makes it all seamless.” 5

which we implemented in the second quarter, we continued to innovate Project Catalog to make it easier for talent and clients to connect. Through upgrades to the platform’s interface, talent can now more clearly highlight and communicate the services they offer through their Project Catalog posts, which allows clients to know exactly what they are ordering and how much it will cost up front. We continued to see strong performance of Consultations in the third quarter, with the average 30-day spend of customers who use Consultations nearly three times that of customers who only buy on Project Catalog.3 We rolled out a new Rate Calculator across Upwork to help first-time talent establish the rates for their work and assist existing talent when thinking about changing their rates. The Rate Calculator allows talent to input monthly expense inputs and the amount of hours talent would like to work every month, to help talent easily calculate the minimum rate they may want to charge their clients. Talent can then compare this rate to the rate of other professionals on Upwork with roughly similar skill sets and services. In addition, we added project management and product management categories to Talent ScoutTM. Talent Scout recruiters are now able to help match clients with the project management or product management professionals they seek by providing a list of qualified talent based on the client’s needs. These product and project managers are pre-vetted and available for jobs of at least 30 days in length. To continue serving Enterprise customers with the powerful tools they need, we made several enhancements throughout the quarter. First, we introduced powerful new search, approval, and reporting and intelligence tools for our Enterprise Suite. Within search, we enhanced functionality to help Enterprise Clients find the top talent they need, when they need it, as smoothly as possible. This enhanced search functionality will help Enterprise Clients find talent with emerging and niche expertise more easily, identify more specific and informative terms for their talent search with help from auto-suggest, and discover talent who are more closely aligned with their Career Innovator: Shantanu Jain “I was in my second semester of my MBA program when COVID hit and we all went home,” said Shantanu Jain, a data analyst based in Indore, India. “It forced me to rethink everything. I borrowed $15 so I could create an Upwork account and send proposals. Four days later, I earned my first $100 project.” Shantanu continued accepting projects on Upwork throughout the pandemic, increasing his earnings and his skill set each time. When graduation finally approached in May 2021, a fintech company offered him an annual salary that was about double the average annual salary for a data analyst in his region. His family considered it a dream job. “I saw an ocean of opportunities with Upwork, and the full-time opportunity to me felt like a small pond. I turned it down. I chose the ocean. It’s now two years later, and I’ve surpassed $100,000 in earnings through Upwork, earning triple the amount that company offered to pay me each year. That was the best $15 I ever spent, as it probably would have taken me nine or 10 years to achieve the same earnings without Upwork.” “Upwork has enabled me and many like me to live our dream. Because of Upwork, I’m able to live close to my parents, rather than 500 kilometers away working for a local company. On top of that, I feel like I am adding value, which provides not just a sense of fulfillment, but drives me to learn and do more and be my best each day.” 3 This is based on the 30 days after the client’s first spend on Project Catalog or a Consultation. 6