Reinventing Work in the Modern Enterprise Era: A Q&A With Upwork’s General Manager of Enterprise Zoë Diamadi

Over the last several years, a number of factors—including the pandemic, shifting labor market dynamics, macroeconomic uncertainties, and technological advancements—have prompted a significant reevaluation of what “work” looks like among enterprise leaders. To help drive the growth and success of our enterprise business, and deliver work solutions to our largest clients, we were pleased to welcome Zoë Diamadi as Upwork’s General Manager (GM) of Enterprise.

Zoë came to Upwork with over two decades of experience as a go-to-market leader, strategist, engineer, management consultant, and innovator at many companies across tech, talent, and B2B. Since joining in June of 2023, she has overseen and evolved Enterprise sales, product, engineering, and operations.

We spoke with Zoë about her critical role in helping enterprises navigate the changing global work environment and dynamic hiring climate, her reasons for joining Upwork, and how she plans to champion the delivery of a best-in-class Enterprise Suite offering to our largest customers.

You have extensive background in technology and business. How has your journey prepared you for your role as GM of Enterprise at Upwork?

My journey has been an evolution through various domains, from engineering to management consulting, and what I like to call “intrapreneurship.” I spent six years as GM of LinkedIn Elevate, building the leading employee advocacy solution for enterprises, as well as time spent in executive positions for LinkedIn’s B2B organization, helping scale its three enterprise business lines.

More recently, I served as an operating advisor at Bessemer Venture Partners. There, I guided portfolio companies on go-to-market topics spanning revenue growth, efficient scaling, and operational excellence for sales and post-sales functions.

These experiences have given me a holistic perspective on enterprises, their business strategies, and opportunities that drive growth. This journey has led me to my current role at Upwork.

I believe we are at a critical inflection point in the future of work, and frankly, "work" needs to catch up to the technologies that are now enabling it to happen. Upwork delivers an end-to-end offering that gives enterprise companies access to a wide breadth of highly skilled fractional to full-time professionals and workforce solutions, enabling them to achieve incredible business outcomes. I hope to help even more organizations discover, and scale with, the transformational value of Upwork.

What motivated you to join Upwork?

Aside from what I feel is the perfect career fit, on a more personal level, I grew up in a small rural place in Greece. Every day, I saw firsthand how many talented and hardworking people were limited by their geography and couldn’t access the opportunities they wanted and were qualified for. These people in my memories represent an untapped pool of highly skilled talent who could have a huge impact on companies. Additionally, these companies and jobs represent a huge economic opportunity for these people to lift themselves, their families, and their communities up.

That’s why I’m so passionate about Upwork—and why I joined.

What do you think are the biggest challenges for enterprises today?

Enterprise leaders across industries face many challenges, while the pressure to maintain and improve balance sheets is as heavy as ever. In our most recent research by the Upwork Research Institute, nearly 1 in 4 leaders told us their top strategic priority this year was maintaining current business operations. Another 30% told us their focus was on improving and finding efficiencies within their current strategy to remain competitive. 13% shared that their top strategic priority was reacting to the unprecedented macroeconomic shifts within their industry.

But the same research revealed an emerging group of leaders (23%) who said their focus was on finding areas to innovate and take risks this year, even with so much uncertainty around them. This emerging group sees the world of work differently—with optimism—and they are both reaping the performance benefits and also pioneering a new path forward in building a better way to work.

Our research of high-performing companies uncovered three common attributes. One stands out to me more than the others. Leaders are embracing the idea of flexible work models as a strategic imperative in navigating uncertainty. The push toward adaptable, scalable work arrangements—and flexible, contingent workforces—is increasingly becoming an essential pathway for enterprises to thrive amid challenges, enabling them to be responsive, resilient, cost-efficient, and competitive. And in today’s world of work, flexibility is fundamental.

Companies that embrace flexible workforces, I believe, will outpace their competitors; those that don’t adapt, will be left behind.

How do you see Upwork helping enterprises overcome these challenges?

Upwork is home to professionals who partner with companies to solve business problems big and small. Organizations everywhere have the ability to access specialized talent and tools they need to get critical work done through our Enterprise Suite. Our Enterprise Suite is our full-service enterprise solution, enabling companies to source and pay highly skilled professionals with ease, efficiency, cost effectiveness, and flexibility, without having to worry about quality of talent or operational complexities.

We connect enterprises with on-demand independent professionals who can quickly and effectively plug in to support everything from accounting and web design to business planning and large language model training. That’s all underpinned by the right mix of account management, human recruiter involvement, compliance, and classification solutions.

Hiring talent through our Enterprise Suite provides the flexibility to scale up and down quickly in response to fluctuating workloads. Companies can adapt rapidly to changing market conditions while reducing burnout and maintaining a lean and efficient team. This allows companies to reduce fixed labor costs (increasing optionality) and embrace a more agile workforce that provides faster speed-to-market for projects and large-scale initiatives.

Enterprise companies often struggle to adapt quickly and at scale. Independent talent on Upwork master new skills and tools faster, and can help big, slow-moving companies keep pace and even stay ahead. The world’s most innovative companies including Microsoft, Airbnb, and Nasdaq are using Upwork every day for mission-critical work in programmatic ways across their business.

Take for instance the success of Michael Contreras, founder & president of Ensemble Consultancy. He’s maintained a competitive edge by leveraging Upwork Enterprise working with companies like NASA, the CDC, Health and Human Services, and the National Geospatial Intelligence Agency.

What are your priorities as we head into 2024?

Our platform shapes who gets work done, increases how much of it gets done, and improves how well it gets done. A key priority since I’ve joined and for the immediate and long-term future is to continue to innovate and deliver a best-in-class Enterprise Suite offering.

I am dedicated to driving technology and talent forward within our Enterprise Suite. This involves leveraging cutting-edge technologies like generative AI, providing added capabilities to ensure Upwork is a true extension of talent teams, seamlessly accessing and hiring expert-vetted talent in a single workspace, and most importantly, ensuring frictionless connectivity across the entire workforce ecosystem.

Our commitment to developing groundbreaking features and nurturing top-tier talent will allow us to remain at the forefront of the industry, meeting and exceeding the evolving demands of our enterprise partners.

What are you most proud of in your first few months at Upwork?

From enhanced customization and support, including an improved dashboard experience, to new approval workflows, self-serve reports, and Payroll billing enhancements, we continue to provide companies with a way to scale a winning strategy. In fact, we are seeing existing Enterprise Suite customers maintain and expand their usage of Upwork due to these enhancements.

Additionally, I’m thrilled that we recently announced a global recognition of the New Product Innovation Award from industry analyst firm Frost & Sullivan, which highlights improvements and enhancements to Enterprise Suite. We strive to continue offering and innovating a reliable and quality product that is relevant and critical to the successes of modern enterprises—and we’re excited that we’ll be able to share even more news on that front very soon.

Lightning round! What's your go-to productivity hack when facing a busy day?

Focus, focus, focus. It’s important to cut through the noise and have a relentless focus on priorities. To do this, I zero in on the two tasks that truly matter for the day. By concentrating on these priorities and letting go of peripheral distractions, I ensure that my energy and attention are channeled into what matters most, fostering a day that genuinely makes an impact. It's not about doing more; it's about doing what counts.

What’s the best piece of career advice you’ve ever been given?

The most valuable career advice I've received is simple but profound: "Opportunities often disguise themselves." It's crucial to recognize that not every chance presents itself in an obvious or conventional way. Sometimes, the most transformative prospects are camouflaged as challenges or unconventional paths. This advice has guided me to stay open-minded, embrace ambiguity, and be proactive in seeking potential where others might not see it.

And finally, if you could have a dinner party with three business leaders (dead or alive), who would they be?

I would invite a trio of visionaries who have left a lasting mark on their respective industries. First, the iconic Steve Jobs—his innovative spirit and relentless pursuit of excellence have inspired countless. Joining him would be Barry Diller, a trailblazer in media and technology, whose fearless approach to business has reshaped the landscape. Lastly, Reed Hastings, a disruptor in the realm of entertainment and co-founder of Netflix, whose ability to foresee industry shifts is nothing short of remarkable. Together, their insights and experiences would undoubtedly make for a compelling and enlightening evening.