Katrina spent eight years at Upwork across three roles: operations, product acquisition, and search. She learned that marketplaces often neglect freelancer investment, that different job categories need different strategies, and that incentives shape behavior in ways that ripple through the entire platform.
Chapters
You know, I'd love to learn a little bit more about what you were working on there and, you know, maybe some of the challenges of it as a marketplace. Yeah.
And I had multiple tours of duty, if you wanna call them that, at Upwork. So I can kind of, and I think each of them sort of taught me a key lesson. So when I first started, I was on the operations team and my goal was, my job was marketplace talent strategy. And so we had really, like many marketplaces do, underinvested in the talent side. We had really invested a lot in the client side. The client is where a lot of the revenue comes in. And we were sort of in a position where, where they opened up a role to say, how should we think about our strategy on the talent side? How should we acquire? How much should we spend for that? How much should we, how should we retain and grow talent? And how do we kind of measure our success in all of those ways? And so the, I think the, It was a really interesting problem, really challenging problem, one that actually like I continued to come back to for throughout my 8 years there. I think the, the most interesting piece and the biggest takeaway for me was how different things look in different kind of sub-marketplaces. So in particular at Upwork, we have different categories of work. So design, for example, being an example, web development, writing, customer service. Customer service is sort of the opposite of logo design. So customer service, it's You get one job maybe every 6 months or 12 months, and you make actually not that much per hour, but a lot overall because you work so many hours a week. On logo design, you might be taking on 50 jobs in one month, or I mean, 50 is a lot, probably more like between 10 and 20 jobs in one month. And so it's very different. The customer experience is really different. How the clients interact with you is different. How the talent interact is different. And so that lends was part of the first, kind of my first job at Upwork. My second big job was around product acquisition, product in particular, and then I expanded to own all of acquisition, marketing, and product. So it was paid performance, it was SEO, organic, as well as the experience, the landing pages and everything else. And I think the biggest lesson for me in that role was the, how much you can do when you work together across these different functions. I really had an appreciation and continue to bring with me that appreciation for if there's a problem for the business, we should solve it together with all of the different groups involved, operations, marketing, finance, product, you know, data science, all of the things that we have at our disposal in order to really solve the problem. So that was, spent several years kind of working on acquisition, top of the funnel. And then my last kind of tour of duty at Upwork was around search and market design and pricing. And so that was I thought that one extremely interesting. Many search engines within Upwork, there's kind of the job search engine, there's the talent search engine, there's also other recommendations and ranking places for both. And so the most interesting thing I thought was just the power of incentives and how whenever you do something, there's always not just a first-order effect, but a second-order effect, just because of how people interact with each other. But the power of incentives to really solve problems in marketplace design to make sure that we are creating the best possible scenario for all parties involved. That was a huge, I think, a huge takeaway for me in that role.
