The CEO of Upwork Reveals the #1 Key to Success in Work & Life

You know a big function of what we do at Upwork is, you know, connecting businesses from the Fortune 100, you know, companies like Microsoft, Airbnb, Cloudflare, all the way down to your local mom and pop company. We connect them with the most in-demand talent in the world. And of course, that's a large part of matchmaking. That's really where we're kind of finding the exact match for not just the company, but the hiring manager, the project, the specific issue that they're trying to solve and going into our tremendous talent pool to find that person. So, there are a lot of analogies to dating sites and kind of matchmaking services generally. And certainly, we always try to pull from the best to figure out how we do that matching better and better every day for our customers.

You know, I think one thing that makes dating sites an interesting analogy for us is, you know, unlike e-commerce where someone can come into a website and kind of browse a bunch of products and then you know many people could order that same product, you know, they have thousands of that product on inventory. In the world of dating sites and the world of Upwork, every person is unique. There's no two people are the same. There's no two, you know, orders you could make of the same thing through our platform. And so we really look at how dating sites kind of bring forward the uniqueness, the specialness of every person and find those very specific attributes that become part of the matching algorithm to get the right person to that individual.

We were founded about 20 years ago really through two very good childhood friends who grew up in Greece and one of them moved to the US and he really wanted to work with his good old friend from Greece who was still back in that country and yet he found in the early 2000s it was not easy to do this and in fact his employer was pushing back and saying well we don't know this person and how do we trust them and how do we know they're doing real work for us and that really led him and his friend to start ODesk which was basically a way to connect remote talent together with a trusted kind of paradigm where there were things like screen captures hourly work guarantees on both sides and all the infrastructure to make remote work safe secure and appetizing for both businesses and talent so that was the early story of our business we've gone through a ton of chapters since then merged with our arch rival Elance and become Upwork in 2015 but really this is a business that's I think at the beginning of the next huge journey and I'm sure we'll talk about that. But AI is changing everything to do with work and we are certainly at the forefront of that both with our product and for our customers.

You know, I've been an entrepreneur since I was a really little kid. And the story there was I grew up in this small town in Massachusetts, a blue collar community. Everyone knew everyone. And when I was 6 years old, my older brother was paralyzed from the neck down very suddenly. He's fine today, but he got this rare autoimmune disease called Guillain-Barré syndrome and suddenly was in the hospital for six months. And there I was, this little kid loving and idolizing my brother and trying to figure out what can I do for him? How can I make his life better when he's in this situation? And I got this idea because he was a huge car nut that when he got out of the hospital, I wanted him to come home in a stretch limousine. Like this was the thing I wanted to do with his friends inside this big surprise, this big moment. And yet my allowance wasn't going to cover that. Like I had no way to fund that type of car rental. So, I got started collecting bottles and cans, turning them in to the recycling center, getting 5 cents each, and thousands of cans later, I had enough money to pay for the surprise limo trip for him home. But what I really got from that wasn't just like the joy of seeing him in that experience. I realized how powerful it was to have earned money as like a little kid, to be able to actually do something with it that really made someone else's life better. And that led me to go on and get a paper. I was probably the youngest in my town to do that, to start a small business called Hayden's House Cleaning. I went around the neighborhood doing chores for people. I went on and started a summer camp for local kids. Like all of these things were important to me, but the throughline was that early experience where I saw the good that I could do as an entrepreneur and seeing my parents who were nonprofit people and were working in communities around the world. We moved to Nepal when I was 11. We lived in Kathmandu and they taught me the importance of not just doing work but doing work with a purpose, doing work that really has a positive impact on people's lives which is what they dedicated their lives to and so that whole experience led me to want to be in business and create new things, create new products but do it in a way that really tied back to personal impact, human impact and that's really one of the big reasons I'm at Upwork today.

You know, about a year after we had moved to Nepal, I remember my first trip back to the US. So, I was 12 years old. I got off the airplane. Within a few hours, I found myself in a US supermarket, you know, probably a Stop & Shop in Massachusetts. And I'll never forget the kind of wonder that I had walking down the aisles and seeing 12 brands of toothpaste, you know, 55 stereotypes, like all of this abundance that previously I had just taken for granted growing up in the US. But now having been overseas for a while and seeing obviously such a different level of access and opportunity in common, I realized as Americans, we are so privileged and we have so much access and things that we just take for granted the rest of the world would, you know, literally move night and day and like do anything to access. So that was a huge wakeup call for me really seeing that disparity and understanding firsthand the privilege of being an American. It felt like I was born with a lottery ticket because of that and starting to figure out how can I help others in the world have access to this incredible opportunity that we have here in the US.

You know, I'll share this lesson with you. I don't know how appealing it will be to people, but actually it was such an incredible experience to be 21, 22 years old and asked to go in and work with some of the biggest companies in the world on core strategic problems that they were struggling with that they did not have answers to. And that was exactly why they were we were there as a firm and why I was being asked to do analysis or research or prepare a presentation that summarized various things. And what I really saw from that is it demystified business and business leadership for me. It made me see that even the people at the top, the most admired and successful people in the world, they too have questions. There's things where they need help. There's things that they don't understand or don't know how to do and could benefit even from someone straight out of college coming in and providing some information or perspective that they needed. So I think for me that really opened up this idea that anyone can be successful in business. We can all have a shot at it and there's nothing especially unique about people who are already very successful like they got there through hard lessons learned but also are still learning every day and that journey is never done.

Culture is everything. You know, I was at Microsoft at a time when there was that famous cartoon of like the different divisions pointing guns at each other because it was just very fraught internally and there was a lot of internal competition and yet I was privileged enough to join a team that was nothing like that. We had this small team that was kind of this ninja force first working on M&A and strategy for the online business which was this new thing at the time and then going on and working on the biggest corporate strategy deals in the company's history including things like the 40 plus billion dollar acquisition bid on Yahoo, the investment in Facebook, etc. And I saw that the culture of our team which was so different than the broader culture of Microsoft was really a huge motivator for me and a reason I stayed and did that work and just loved it and grew so much. Whereas once I realized I wanted to go into product management and do something else with my career, I knew going into the rest of Microsoft at that time in that culture was just not appealing at all. And so I've carried that with me in thinking about how do I build at Upwork the right culture that really attracts and retains, that gets the best out of people and is not political, is not discordant internally but really has us all moving in the same direction.

We have a value called build and break fearlessly. And we have a number of company values. We have five total values, but this one is the one that I think really animates our culture and our reason of being the most because we're a company that's built to break the status quo to create possibilities for people and businesses that did not exist before and would not exist without our platform. So, we need to be fearless every day examining what needs to change not just in the ecosystem outside and where we're trying to influence stakeholders, customers, etc., but how do we need to build and break our own culture or our own ways of working or our own practices to actually achieve these goals for our customers? So this value for us cuts very deep and shows up in all aspects of our work and is I think the thing that keeps us innovating at the edge of the comfort zone and pioneering our space in a way we could not do if we weren't so anchored on this value.

There's so many. I mean, we just had a huge announcement on Tuesday, which was around this new business unit and a brand we launched called Lifted, and we created this business through two acquisitions plus our own existing enterprise business put together in this new structure. And I will say this is probably the biggest build and break fearlessly moment that we've had because this required us not just to do acquisitions or change our product or change our sales strategy. It actually caused us to restructure our business and create this unit and completely change our operating model in order to be able to serve our customers the way we knew they needed to be served. And so this one I think is a great example of how we went deep inside and not just outside in terms of how we apply this value and really did the hard work to set us up for this next great chapter.

Yeah. So, I joined the company in 2011 actually as a product manager. I found the head of product at the time was willing to take that bet on me transitioning from strategy and M&A and this other part of my career into actually being a builder. And then I grew up to be the head of product and then ran marketing before becoming CEO five and a half years ago. But what I saw with being in product was this was such an amazing throughline between really understanding customer needs very deeply and then being analytical and focused about how to action those needs and also being very creative in terms of solutioning design, product development. And then of course closing that feedback loop by seeing what happens when you ship those products, how customers engage with it, how they respond and then using that of course to come back to the beginning of the process all over again. So, I loved how I got to be so front and center with customers, understanding their problems, and then applying them directly into changes in our business to address those problems.

This happened really naturally for our platform actually. We started with a really strong foothold in technical work. So we had a lot of Eastern European talent and others around the world doing web and mobile software and application design all of that work kind of in the early 2000s. And then you're right, we also had this very stronghold with design and creative work. But what we saw is customers would come in, they'd have something in mind like build a website, but that was not something that just a designer or a developer could do in isolation. They needed design, development, marketing, they needed the full spectrum of skills to execute these bigger projects. So very naturally, they started looking for and finding talent on our platform that drove that flywheel where now we have over 130 categories of work, 250,000 AI specialists globally. And the composition of our marketplace continues to shape shift based on client demands, which is an amazing aspect of our marketplace.

We stay focused on solving our own customers problems. And of course, we look at what others in the marketplace in the ecosystem are doing, but we have such a unique solution that actually no one has replicated. There's no one that does what we do. We do complex large project work. We have deep relationships being fostered between clients and talent on our marketplace. This is not small transactional stuff or throw it over the wall to somebody talented. So, our distinct value proposition and market positioning is something that we see as a huge asset that we can continue to expand on with things like our AI features and what we're doing there with things like this enterprise expansion, what we're doing there. And we see ourselves bringing to the market solutions that no one else has and frankly are really disrupting some of the legacy players who've been around for a long time but aren't tech enabled, don't have marketplaces, don't have the set of talent and other capabilities that we have.

It's a great question. I mean, we talk to customers every single day. We're on the phone, on Zoom, in person. I do an AI customer council every month where I gather customers who are focused on AI and are using our platform for AI and talk to them about what's current and on their minds. So, we have a ton of these channels for getting that feedback. But you're right, David. One of the things I think is critical about a product manager and about a product company is we can't just build what we're asked to build. We have to go beyond that and have a bigger vision for where we're headed that customers may not even fully grapple with yet. They might not even be there yet, but we've got to be building that vision and making it real for them. So, we also do a lot internally in terms of putting stakes in the ground around how we see the market evolving in the next few years where things like AI will transform our opportunity, visioning that out, and then building a roadmap that is giving incremental wins to customers along the way. So, they're seeing those benefits. We're not waiting until that big reveal, but we're building towards something that once we get there, everyone will look back and go, 'This is totally different. This is totally transformational.'

I think clarity is probably the most important thing if I look back and at every step of the way I really focused on bringing clarity to hard problems that we didn't know how to solve or hadn't resolved yet. Also bringing clarity to what's the actual situation in the business because as a leader we have to start with a clear and shared narrative of what's the market and what's our situation in the market and what's the problem to be solved or the job to be done. Then we have to articulate that vision of what could it be? What are we driving towards? Where are we trying to get to? And then the third thing is executing that plan, building and mobilizing the plan and the people to get there. So for me, it's always started with clarity. If we don't know what problem we're solving or we don't know who we're solving it for, we can do all these other steps and they will not move the needle on our ultimate goals.

So in January of 2023, basically two months after ChatGPT had started to land on the scene, we sat as a leadership team and had a discussion about what did AI mean for our business. So, if we remember at that time, two months in, tons of open questions, plenty of healthy skepticism. There was a raging debate within our own team of should we try to act on these new technologies? Should we be incorporating them into the roadmap that we just built for that year? We just finished that whole planning process or do we wait and see? And there were advocates on both sides. That was a moment where I felt it was critical to step in and really have a strong voice and clarity around my view, which was this technology will change everything. We have to be a first mover, not a last mover here. We can't wait to see what others are doing. And the only way we're going to be successful is if we get our hands dirty and start to learn by doing. Now, at the same time, we couldn't just throw out our whole roadmap and start over again because we had a ton of goals to achieve. We knew a bunch of problems we needed to solve with existing capabilities. So what we did was isolate a small team to basically go off-site essentially in our virtual mode and just focus on the question how would we build Upwork today and what would it look like if we built it premised on an AI foundation and that work and that team came back with some incredible insights, huge inspirations for us from a vision standpoint in terms of putting stakes in the ground of where we were going in the medium term and then we gradually pulled pieces of that into the roadmap and started to build chunks of that idea as part of our AI strategy. But that was a defining moment for us in terms of making that pivot and really committing to something that at the time, there was still a lot of question marks about.

I think I faced a lot of tests over the many years not just leading this business but also just rising up through a number of roles and there was one formative experience for sure that happened during the outbreak of the Ukraine war started in February of 2022 where I think for me that was actually for our business a significant crisis. We had 10 to 12% of our talent globally in the war-torn region, we had 12% of our own team internally that we work with also in that region. So we had internal exposure, we had customer exposure, our revenue was at risk like all of these things and most importantly I was faced with the ethical question to some extent of do we continue to operate in Russia and Belarus or not and there were advocates from our customers on both sides, advocates internally on both sides. Ultimately, we were the first company in our space that made the decision to suspend operations in Russia and Belarus. And that was an agonizing decision. Through that, I think I really learned and felt that adage that it's lonely at the top because there was no one who could tell me with any intelligence like what really needed to happen. And only I had the information perspective to make that really tough decision for our customers who were directly impacted. Our platform is a lifeline for so many of them. And so turning it off in a certain market is extremely risky and goes against our value system. At the same time, we knew we couldn't operate and deliver our brand value and our purpose in these markets given sanctions and changing conditions on the ground that just made it untenable. So this was a very difficult choice. But I think going through that and realizing the full responsibility that I had to our customers and making that decision with clarity early on so that they could all make their own decisions going from there and we could continue to operate effectively as a team was essential. So I think it's been moments like those, David, that really tested us and our leadership and our cultural fabric and me in terms of making a bold and clear decision early. And I've always seen that those types of decision-making moments play out better when you can be clear and move fast and make a good decision versus wait and wait for more information, etc.

I spent a lot of time myself just using these different tools. I'm a big ChatGPT user. I experiment with Gemini a lot. But I haven't had as much success with that. And I look at and test out category specific tools. So I'm not a developer, but I will watch tons of videos of how people are using tools like Cursor, v0. Of course, I talk to our own team all the time about this because we are using those tools internally, but as things come out, I'm constantly reading, experimenting, watching, and participating in keeping my own AI skills sharp because I have to roll that model out for my team. No one in my company is going to believe that I'm serious about AI unless I'm showing up using these tools, pushing on them where they're not using the tools, etc. Of course, we also have some programmatic things in place. We started an AI certification program where we have a bunch of initiatives that are really focused on targeting and unlocking this value, but personally, I feel I need to champion this both by doing and showing up with our teams to really advocate for our AI adoption.

Totally. And we've seen everything internally. We've always had this cohort of early adopters who were leaning in, advocating. We've bought two AI companies in the last two years. So that's brought in a lot of super forward-leaning AI talent, including our head of AI who came in from one of those acquisitions. But you're right, there's also a long tail of other people who've been worried or skeptical or feel like maybe they don't have permission to use these tools. So we make it a constant habit. Every week we're talking in our weekly mini all-hands meeting. We're talking about and showcasing how people internally are using these tools. We've created workshops and webinars and now really communicated to everyone that the expectation is they are using these tools. So it has taken in some places the snowball needed to start rolling before speeding up but now it feels like it's moving really fast in terms of executing on this opportunity and getting everyone in the company involved in it.

It's my top priority. It has been so important because you're right, there's skepticism, there's fear, people worry even in our company about their jobs being replaced by AI. I mean, this is a widespread phenomenon. So, I have had to be very clear and it's one of those things like repeat, repeat, repeat until people are sick of hearing it. And I'm sick of hearing myself say it, but repeat what our goals are and really reassure people as well as push them and challenge them in terms of where we're going. And this is, I think, essential for every leader. It's not going to happen in the business without each of us really leaning in and driving this change.

I used to be very naive on this topic. When I was 22 at McKinsey or Microsoft, I was thinking it doesn't matter that I'm a woman. Like, that's not going to hold me back. No one's going to penalize me for that. And of course, in the last 20 years, I've seen tons of instances where I'm underestimated. I'm looked over. I'm mansplained to constantly just because people think oh she can't know what she's doing or she can't take this on. So of course I've experienced that throughout my career. I think the thing that has been really interesting as the CEO I've really realized that in our culture there's kind of two types of women leaders who are stereotyped. There's

I am neither the soft and fuzzy mom nor the cold-hearted jerk. I bring genuine warmth and care for my team and customers, but I'm also hard-driving, decisive, bold, and analytical. People struggle to see both sides, so I need to communicate and educate my team and stakeholders about who I am and what I stand for, because the stereotypes for women leaders don't apply to me.

Unfortunately, many capable women hold themselves back from the next step because they feel they need to do a little more, prove themselves more, or learn more before taking the job they want. A piece of advice I give is: if you're thinking about doing that thing, don't do three things first. Go do it now. You're ready. That's what a lot of men do—they don't wait for the perfect profile. As women, we can push ourselves on that because our culture doesn't always foster it.

About three-quarters of our workforce today is freelancers, and that's been true since we were a small startup. More companies are shifting toward a smaller core of full-time employees and a larger group of contingent freelance and third-party vendors. Leaders need to move from thinking in FTE units to thinking in skills, projects, or efforts. Once you break down the work that way, you might not need a team of 10; maybe four or five specialists can focus on that project. It's a different mindset about the unit of work and how to scope it.

We start with the goal and the timeframe. Is it something that will endure beyond that? We also look at compliance and how much control and direction are needed versus more autonomous work. But for us, every question starts with the premise: why can't we do it with freelance talent? That's our default. People have to justify adding headcount.

The first thing is to avoid mistaking a remote-forward workforce for never getting together in person. Our model combines fully remote members with strong cadences of in-person gatherings for building social context and relationships. Remote teams must have in-person touch points. Then you need clear remote work practices, like cameras on for every meeting. We also have weekly half-hour touch points to build culture and share what's happening across the business. Every company has to find what works for them.

Two things have helped us. First, in-person relationship building—dinners, hikes—builds psychological safety so people can have conflict and feel it's okay. They know it's coming from positive intent. Second, you can't have just one dimension of communication. When there's conflict, we agree to resolve it quickly—phone call or in-person meeting immediately—so it doesn't fester. Never let a conflict roll into the next week; resolve it by Friday.