1x Q4 and Full-Year 2022 Shareholder Letter 1

In 2022, in the face of a dynamic environment, Upwork made meaningful progress executing on our strategy to innovate, evangelize, and scale our work marketplace. We delivered innovative new products and features, including Project Catalog Consultations and Project Tiers, Upwork Academy, and our new Client Marketplace Plan for client pricing. We continued strengthening our Enterprise Suite and our investment in brand marketing delivered measurable results. Through these innovations and investments, we made it easier and more productive for clients and talent to connect and manage their work and relationships on Upwork. For the full-year 2022, Gross Services Volume (GSV) grew 16% year-over-year to reach $4.1 billion and revenue grew 23% year-over-year to reach $618 million. GAAP net loss was $(89.9) million and our adjusted EBITDA came in at $(4) million. In the fourth quarter of 2022, GSV grew 5% year-over-year to once again exceed $1 billion and revenue grew 18% year-over-year to reach $161.4 million. GAAP net loss was $(16.5) million and adjusted EBITDA reached $1.1 million. The fourth quarter demonstrated a continuation of the macroeconomic trends that we saw in the third quarter. We observed corporate caution during budgeting and planning cycles, leading to softer client acquisition and retention trends across our customer base. This behavior is consistent with our experience in past uncertain macroeconomic environments, in which we have typically seen companies moving through a sequence of phases. In the first phase, companies will reduce their costs and freeze hiring budgets as they grapple with uncertainty or the onset of macroeconomic weakness. This is when we may see a headwind from customers reducing overall budgets. As they move into the second phase, companies realign their cost structures in a more efficient manner and start to redeploy resources to solutions such as Upwork, where they have confidence they can deliver the best returns. This is when we have typically shifted from seeing a headwind to a tailwind. In the final phase, as the economy shows definitive signs of improvement, companies ramp up budgets and seek to aggressively hire, characteristically turning to our solution more than others because of the speed and flexibility we offer. This is when our momentum gathers further. Today we see many of our customers are in Dear Shareholders the first phase, realigning their budgets, with some moving into the second phase. Although this dynamic is creating near-term headwinds in our numbers, we have our eyes on the opportunity ahead of us. We are taking proactive steps to position Upwork for the full benefit the second and third phases can offer as we provide companies with rapid access to cost-effective, highly skilled, global talent and flexible solutions to meet their workforce needs. To capture the opportunity ahead of us, we continue to innovate to advance Upwork’s evolution from the largest global freelance marketplace to the world’s work marketplace. Earlier this week, we announced our end-to-end solution for full-time hiring. This is the next step in the journey we started in 2021 to expand our offerings to support all the ways our customers want to work on Upwork. With this launch, we are bringing to bear more than 20 years of worker classification expertise as well as existing and new technology solutions to enable our customers not only to form the trusted, long-term working relationships that Upwork is known for, but to do so via a complete set of full-time hiring solutions now available to all our customers—Enterprise Clients and Marketplace Clients alike. This strategic expansion affords both clients and talent further flexibility and choice in how they work together, and delivers a first-of-its-kind, end-to-end solution that enables businesses to easily, quickly, and cost-effectively find, vet, hire, and pay talent who are interested in full-time work from all around the world and offering more than 10,000 skills. Addressing global full-time work is a natural extension of our existing work marketplace and supports both our mission and the natural progression of work behaviors we see on Upwork today. Embarking on a brand awareness campaign to introduce ourselves to the many companies and hiring managers who have not been previously aware of Upwork has been an ongoing priority. Our goal has been to raise unaided awareness across a broad audience and ensure that companies and hiring managers understand our compelling value proposition. As companies are increasingly scrutinizing their internal resources and costs, we believe now is the right time to educate them about our solutions and the cost savings we can provide. We are pleased with 2

the results thus far. With our “This Is How We Work Now” campaign, which we launched in September 2022, we have seen even greater progress increasing brand awareness than we expected. Since the September launch of our new campaign, unaided awareness has grown more than 30%, with unaided awareness among large businesses (1,000 employees or more), which represent the biggest segment in our total addressable market (TAM), growing by more than 140%. From the third quarter to the fourth quarter of 2022, ad recall, which measures the impact of brand campaign messaging on our chosen target audience, grew 45% among large businesses, and we saw 58% growth in top-of-mind awareness, which is a measurement of being the first brand mentioned in a category. Looking at the year ahead, we also recognize the macroeconomic climate has changed rapidly, and we are moving to reduce our brand working media spend by approximately 12% in 2023 compared to 2022. Given the strong focus on measurability and testing that we have deployed to date, we are able to make this reduction in costs while still driving the outcomes we are seeking with our investment and campaigns in 2023, targeting significant continued growth in unaided awareness as well as delivering insights into how this investment impacts our downstream metrics and overall marketing efficiency, as our campaigns evolve and our data sets mature. This approach is tailored to achieve our customer- and business-impacting goals while giving us more room to respond to new macroeconomic realities and continue to make strong data-informed decisions about this investment area in the future. In our Enterprise business, revenue grew 22% year-over-year in the fourth quarter. We continued to make progress in ramping our salesforce and educating our prospects and customers on the new features and enhancements we launched in the year, including flexible approval workflows, talent performance reports, and user activity reports. In the fourth quarter, we signed 26 new Enterprise Clients, as we saw the average length of the sales cycle extend by nearly 20% as corporations made changes to and delayed their budgeting and approval processes. This also resulted in an unprecedented increase in prospective customers pushing late stage deals into 2023 as they worked through these changes. Our new Enterprise Clients included high-quality companies like HTC, JLL, Maaco, Lucid Motors, and Sweetwater Sound, who have turned to Upwork to help them solve their workforce needs in this evolving work environment. The decision of these leading companies to source talent through Upwork is a testament to the real value we bring, through both the quality of talent on Upwork as well as the ease of use and cost efficiency we provide. 3 Generative AI & Upwork It has become abundantly clear in the past few months that knowledge work will be turbocharged by artificial intelligence (AI). Operating the largest work marketplace that connects businesses with independent talent from across the globe, we have seen many emergent trends in work over the last two decades and are excited to be at the forefront of these exhilarating changes with our customers. Upwork has always been the destination for technology pioneers looking for the critical human capital they seek—including for all stages of their AI and machine learning workflows. In fact, we have been working with a large AI research and development laboratory as our client for several years, providing them with the knowledge workers they need for many aspects of their work in model development and training, full stack development, natural language processing, script writing, technical writing and support, content curation and more. We are excited to continue serving organizations pioneering this exciting new technology. With the advent of AI, we can already see multiple classes of opportunities, including the opportunity for our talent to deliver better outcomes at higher speeds and lower costs to their clients through the deployment of AI, unlocking greater customer delight and even more demand for their services. We also see new job opportunities emerging—not just for those who supercharge their own work with AI—but also for new roles that are created for work directing, tuning, and retraining AI models. While this new era is still in its infancy, we have seen generative AI related searches increase 3900% when comparing the most recent four weeks against the first four weeks of the fourth quarter of 2022, with job posts related to generative AI services also growing more than 1400% in that same time period. We are moving quickly and thoughtfully to understand and address our customers’ greatest priorities. We have already updated our Talent Marketplace knowledge graph—the taxonomy that powers matching on Upwork—to reflect the exciting new roles in this space and added new Project Catalog categories to begin showcasing what’s available from Upwork talent in this area. We are just at the beginning of ushering in this new opportunity.

We are making strong progress addressing the internal Enterprise sales operational growing pains we experienced last quarter. Our efforts to close the gap on them have started to fuel improvements in top-of-funnel activity late in the fourth quarter, and we expect to see our sales reps’ productivity normalize as we move into 2023. Barring further deterioration of the macroeconomic environment, even with the elongated sales cycles we have experienced recently, we expect to be back on track with our Land team at full productivity and performance by the third quarter of 2023. We see a clear path to reaccelerate our momentum in Enterprise and believe the Enterprise opportunity remains as attractive as ever for Upwork. In 2023, we are proceeding in a balanced and nimble manner and focusing on the things that we can control while being ready to make the most of opportunities that may arise. For example, in December, we made a significant change to our organizational structure, moving from purely functional to a business unit composition. With this new organizational framework, we have been able to strategically reallocate resources from a broader, more fragmented portfolio of investments that at times represented incremental opportunities, to a more concentrated set of resources in all of our key business unit areas, each helmed by a leader laser-focused on delivering customer and business outcomes with attractive growth and return opportunities. As a result, we have set ourselves up for the future with increased efficiency, agility, and accountability throughout the organization. We remain committed to achieving our goal of adjusted EBITDA profitability in 2023 and aim to increase our adjusted EBITDA margin by a few hundred basis points per year as we progress toward our previously communicated long-term target of an adjusted EBITDA margin of 30-35%. A critical part of our strategy is to remain disciplined with regards to our cost management, and we are focused on increasing our operating leverage, targeting 2023 revenue growth in excess of operating expense growth. We are entering 2023 on offense, ready to capture the opportunity ahead of us. With our leading, cost-effective solutions, we are uniquely positioned to meet customers where they are, and benefit as customers learn about and turn to Upwork for their full range of talent and work needs. We remain steadfast in our long-term vision and will continue to innovate, evangelize, and scale Upwork as the world’s work marketplace in 2023 and beyond. 4 Career Innovator: Jacqueline DeStefano-Tangorra After graduating with a bachelor’s degree in accounting, a master’s degree in business administration, and becoming a licensed certified public accountant in New York at age 23, Jacqueline DeStefano-Tangorra secured a position at a Big Four accounting firm in 2015. “I had what many would consider to be a dream job at a prestigious firm, but after seven years, I knew something was missing,” DeStefano-Tangorra said. Throughout her tenure at the Big Four accounting firm, DeStefano-Tangorra held various roles that increased in responsibility—from financial auditor to project manager to product owner, and finally becoming a lead business intelligence consultant. “I enjoyed the challenge of serving a diverse portfolio of businesses and industries, but I craved more opportunities to serve clients in a way that better aligned with my creativity and core values—including personal flexibility and gaining financial freedom.” “When the pandemic hit, like many of us, I grew keenly aware of the value of time. I pursued upskilling opportunities that would enable me to pivot my career—then I found Upwork, and everything changed,” DeStefano-Tangorra said. In just two years on the platform, her earnings surpassed her salary. “This platform has changed my life. Upwork provides endless opportunities to meet and work alongside some truly incredible clients. As a result, I have built long-lasting relationships with enterprise companies, franchise owners, and small businesses, allowing me to create a trusted brand and scale my business. Upwork allows me to live the life that I want, and I am proud to be a part of Upwork and all that it represents." Jacqueline DeStefano-Tangorra

Q4’22 Business Highlights Innovating the Work Marketplace Throughout 2022, we focused our product innovation on making it easy for clients and talent to match and start working together quickly; ensuring a high-quality, delightful experience; and establishing trusted, repeat relationships. These three guiding principles work together to create a flywheel that enhances our market-leading two-sided marketplace and drives our customers’ success as well as our own, making Upwork the go-to platform for clients and talent to get work done together. As we mentioned earlier, this week we launched a new end-to-end solution that makes full-time hiring easily available to all customers for the first time. This is an evolution for our company as we bring together all of the different ways to work in one place, making it simple and seamless to convert working relationships from freelance or fractional to full-time as needed. This helps take the complexity and stress out of embarking on any type of project or work endeavor, at any time, with anyone—almost anywhere around the world—while saving both time and many of the potentially exorbitant costs resulting from making a bad full-time hire. The cohesive solution leverages both new capabilities and our longstanding expertise to enable our customers to discover, trial, hire, and pay (or be hired and paid for) full-time opportunities on Upwork, including a mutually beneficial way for clients and global talent to trial a contract-to-hire working relationship before they commit to a long-term, full-time engagement. 5 Career Innovator: Rehan Hussain Full-stack developer Rehan Hussain’s father came to the United States from Pakistan with a few hundred dollars in his pocket. Last month, Hussain surpassed $1 million in earnings on Upwork. “My father came to America chasing his dream for a better life,” Hussain said. “He worked his way up from delivering pizza to eventually owning his own restaurants and did everything he could in order to provide for his three children and ensure they got an educational opportunity.” After graduating from Syracuse, Hussain worked as a developer in a corporate role for a few months before he decided to strike out on his own. Inspired by his father’s ability to make bold moves, Hussain always knew he wanted to be an entrepreneur and saw the opportunities that working on his own would offer. “Fast forward to today, and my annual earnings on Upwork are at least three times what I probably would have been making if I had stuck with that traditional role,” Hussain said. With a baby on the way, he and his wife are grateful for the opportunities Upwork offers. "My father taught me the value of tenacity and hard work, and I proudly bring those traits to the table every day in my career as a freelance engineer. I always dreamed of being a father, and come August, when my wife is due, I’ll have all of the flexibility, financial stability and freedom I could want—as well as the opportunity for my child to grow up seeing that anything is possible.” Rehan Hussain