Upwork at Goldman Sachs Conference: Strategic AI Expansion

On Thursday, 11 September 2025, Upwork Inc. (NASDAQ:UPWK) took center stage at the Goldman Sachs Communicopia + Technology Conference 2025. CFO Erica Gessert provided a strategic overview, highlighting Upwork’s robust Q2 performance and its future growth plans, while acknowledging challenges in the macro environment. Key focuses included leveraging AI, expanding into the enterprise market, and enhancing service offerings to drive growth.

Key Takeaways

• Upwork reported a "breakout quarter" in Q2, driven by AI and enterprise market expansion.
• The company aims to achieve a 35% adjusted EBITDA margin while continuing revenue growth.
• AI-driven improvements generated $80 million of GSV in Q2.
• Upwork’s strategic acquisitions aim to capture a larger share of the $650 billion enterprise contingent labor market.
• Future growth is expected from AI integration and increased take rates.

Financial Results

• Q2 was highlighted as a breakout quarter, with growth rates 10% to 15% higher than traditional staffing agencies.
• Adjusted EBITDA margin reached 29.3%, with a long-term target of 35%.
• Connect revenue grew by 20% in Q2.
• Business Plus GSV saw a 190% increase quarter over quarter.

Operational Updates

• Upwork’s strategic priorities include growing the AI category, which saw a 30% growth in Q2.
• AI implementations on the platform include automated job post creation and talent interviewing.
• The company acquired BubTea and Ascend to expand its enterprise solutions.

Future Outlook

• Upwork anticipates resuming GSV and revenue growth, particularly from enterprise requisitions in the latter half of 2026.
• The company plans to increase its take rate, currently around 19.5%, by offering premium services.

Q&A Highlights

• Initial concerns about AI’s impact have shifted to viewing it as an opportunity for market expansion.
• Despite an uneven macro environment, Upwork is focusing on larger projects and enterprise client growth.
• Capital allocation priorities include organic growth investments and strategic M&A.

Readers are encouraged to refer to the full transcript for a detailed account of Upwork’s strategic plans and financial performance.

Full transcript - Goldman Sachs Communicopia + Technology Conference 2025:

Eric, Interviewer: We’re just at time. I think we’re going to kick on with our next fireside chat. It’s my pleasure to welcome the team from Upwork to the conference and have a fireside chat with Erica Gessert, CFO. Erica, thanks so much for being part of the conference.

Erica Gessert, CFO, Upwork: Thanks for having us, Eric. Delighted to be here.

Eric, Interviewer: Okay, let me do a little bit of background and then we’ll get into the conversation. The first thing to say, Prabhu, before we start, Upwork Inc. would like to remind you to join the fireside chat today. They will make forward-looking statements, which involve risks and uncertainties that may cause actual results to differ materially from those statements. For discussion of the material risks that could affect the company’s actual results, please refer to the risk factors section of Upwork Inc.’s most recent quarterly report on Form 10-Q and other SEC filings. The company will also discuss both GAAP and non-GAAP financial measures. Statements made today are effective only today and will not be updated to reflect subsequent events or circumstances that may arise. Erica Gessert is the Chief Financial Officer at Upwork Inc., where she oversees Upwork Inc.’s global finance team and operations.

She has more than 20 years of finance operations, analytics, and investor relations experience supporting technology companies. Prior to joining Upwork Inc., Erica served in a number of senior executive roles for PayPal, most recently Chief Transformation Officer reporting to the CEO, and she held finance and investor relations roles at Sprint and Virgin Mobile USA.

Erica Gessert, CFO, Upwork: Yes.

Eric, Interviewer: There we go. Okay. We can just do follow-up questions on that, or we can talk about our career trajectories. That’s amazing. Okay. Erica, you know I always like to start with just giving you the floor a little bit to level set. For those who are a little bit less familiar with the company or just even coming out of Q2 earnings, how are you framing for investors where the company sits today and sort of the journey you’ve been on?

Erica Gessert, CFO, Upwork: Thanks. For those who don’t know Upwork, we are the world’s largest AI and human-powered work platform. Companies of all sizes, up to Fortune 100, all the way to solo entrepreneurs, come to our platform in order to find talent to get work done. We are the largest at-scale company of our kind, and we’re unique in that we are a true tech-enabled platform to enable work. We had what I would call a truly breakout quarter in Q2. We’ve consistently outperformed the rest of the companies in our industry, which is the human and capital industry, so staffing companies. Over the past several years, we’ve consistently had our kind of growth rates be 10% to 15% higher than the other staffing agencies in our industry. In Q2, we really outperformed every single metric, financial metric, top and bottom line. It’s been a really exciting time for us.

Eric, Interviewer: We’re building off of that. The company has been dealing with significant macro volatility for quite a long period of time. You have this Q2, you put up these excellent results. Talk a little bit about the momentum building in the business that’s within your control as you look out to the second half of the year and 2026, because there are a lot of things you guys are building as a company that are within your control and also operating in what continues to be a volatile macro environment.

Erica Gessert, CFO, Upwork: Yeah, look, I think the macro environment isn’t doing anyone any favors, and the uncertainty, if anything, is getting stronger, not weaker. What we’ve been doing really over the past couple of years is putting ourselves in a position to be macro-agnostic. The human capital industry does tend to have impacts from the macro. If you look at the BLS data and kind of all the chaos there, the labor market is volatile, to say the least. We’ve been able to really divide ourselves from that. Over the past few years, our kind of GSV, which is our volume-related metric, has been relatively flat compared to, like I said, negative double digits in the rest of the staffing industry. We’ve been taking share, but we have now, what we’re saying is bent the GSV curve, and we are now poised to resume GSV and revenue growth.

We actually said at the end of last year that we would enter 2025 and have a relatively flat kind of volume-related year as we retooled and prepared ourselves for growth in 2026. We are now well ahead of that plan, and we are poised to start showing GSV growth now, GSV both revenue and GSV growth now and into 2026.

Eric, Interviewer: Okay. With that in mind, one of the things I know we’ve spoken about on public earnings calls is striking a balance between top-line growth and continuing to make progress on the margins. When you layer out your strategic priorities and we think about the macro environment, what you just said, what do you remind investors about the priorities between revenue growth and margin trajectory?

Erica Gessert, CFO, Upwork: Thanks for bringing up our margin growth. Over the past couple of years, we’ve gone from when I came into the business, we were relatively flat margins. There were really 0% margins. Last quarter, we posted 29.3% adjusted EBITDA margin. A really fantastic margin trajectory. At the same time, what we did was, of course we’ve made adjustments to sales and marketing and other things, but we’ve also narrowed our R&D portfolio and really focused on three strategic priorities that have enabled us to both grow margins and prepare ourselves to resume GSV and revenue growth. We’re doing it all. The three strategic priorities that we’ve focused on are really focused on expanding our access to relative pockets of TAM. First and foremost, of course, is the growth of the AI category itself, which is a great tailwind for us. We think about that in two ways.

Number one is the growth of the AI category itself, which actually reached an inflection point for us in Q2 in that the growth rate of that category increased. In Q1, the AI category, our fastest growing category in the platform, grew 25%. In Q2, it grew 30%. We actually see that growth rate continuing to accelerate. That’s a real tailwind for us. The other enabling factor of kind of the AI-ification of the overall work industry is the implementation of AI on our platform. We have what we call UMA, which is Upwork’s mindful AI companion on our platform. If you think about the hiring process in general, it is what has been historically friction-filled, right?

People come onto the platform, a client comes on, a business comes on, they write a job description, they post that job, talent comes on, they have to write job proposals, they post those, the client has to review them, read them all, and then interview talent. All of that is now taken care of by AI. UMA writes the job post, UMA writes the job proposals, UMA can now interview the talent and recommend talent to the client. Coming soon, we will also have UMA start to create milestones for projects and project manage projects. All of those things are being completely enabled by AI and reducing friction. What we saw in Q2 is that about $80 million of GSV is now driven by these improvements on the platform, and that is just set to increase.

Eric, Interviewer: Okay. You talked, and it’s been an interesting journey we’ve been on. You and I have talked about this before, but the initial reaction to AI was quite as a potential negative impact on the company. I think people have slowly come around to seeing some of the TAM expansion opportunities tied to AI. Has the definition of what you guys are looking at from a broader market opportunity and how you define the future of work changed as a result of what you’ve learned, especially in the last couple of quarters?

Erica Gessert, CFO, Upwork: Yeah, absolutely. Look, I mean, you know, people, I think, especially when I came on a couple of years ago, it’s sort of the old Oscar Wilde quote, you know, the rumors of my demise have been greatly exaggerated. I think that people thought of AI as a real threat to work overall. What we’ve seen is a very different story. We’ve seen, number one, the growth of the AI category itself, as I said, has been a real tailwind. We also see AI truly augmenting other categories on the platform that aren’t classically thought of as AI categories. The implementation of coding enablement products, you know, kind of AI products are actually helping our talent get work done faster and just increasing their portfolio of work.

We’re seeing other categories like video and animation, contract law, other things like that that people thought would actually be disrupted by AI actually start to be accelerated by AI. This is a real benefit for us. I think another phenomenon that people need to start to kind of understand better is the fact that as AI starts to enable work, it’s not full jobs that are going away, right? It is partial jobs. Human in the loop and the need for people to enable these AI solutions is going to continue. What that means is that for companies like us that are offering contingent labor solutions, that can actually be a tailwind for us.

Eric, Interviewer: Yeah, okay, understood. We did touch a little bit earlier on the macro environment overall, and it’s been interesting the way you guys have talked about a whole host of demand signals you’ve seen over the last 6 to 12 months, elements of what drives client growth, what drives client spend. Can you just level set on what you’re seeing in the macro environment and bring it back to how it informs client growth, client spend, and then differences across types of clients even, which you’ve talked about before?

Erica Gessert, CFO, Upwork: Yeah, sure. I mean, we’ve consistently seen the macro environment, as we know, is uneven and will be for some time. I think, like I said, we have created a set of priorities, and I’ve only touched on a few of them so far, but a set of priorities that is really enabling us to perform regardless of the macro environment. We will and are going to resume growth very presently, despite the unevenness of macro. What we see from our clients is, at the very top of the funnel, we continue to see pressure from, you know, kind of new client demand growth. At the same time, what we’re seeing is that our projects are getting bigger and bigger on the platform.

Our customers are coming and trying to look for contingent labor solutions to enable, you know, both, you know, AI solutions as well as, you know, all of the 130 categories of work on our platform. The places where we may see sudden substitution of AI is at the very smallest, most transactional types of work. Now that’s about 5% of the GSV in our platform. The rest of the GSV in our platform, bigger jobs, kind of larger, more complex jobs are simply being AI-enabled, and we’re seeing kind of wallet growth there.

Eric, Interviewer: Okay, understood. I do want to get into some of those strategic priorities because this is a technology conference. We’ll turn to AI next. I’m sort of contractually obligated, I think, to bring that up. You’ve been at the forefront of trying to push AI into elements of all parts of your platform. Talk about where the AI integration into the freelancer and the business sides of your platform sit today and how you think that might scale in the future and what it might mean for growth.

Erica Gessert, CFO, Upwork: In Q2, what we saw was the very early implementations of kind of AI-enabled platform are driving about $80 million of GSV, and that’s just the very beginning. What we see is both on the freelancer side, so freelancers adopting AI tools, and we actually have a subscription product today called Freelancer Plus that offers kind of an Upwork ChatGPT-like product to access to our freelancers. There’s an opportunity for us to offer preferred access of AI tools to help freelancers enable their work even to an even greater degree in new subscription products, and that’s just going to be a growth mechanism for us. Another very important area of growth for us is a product that we call Business Plus on the marketplace. That product is a premium take-rate product. It’s in the very early innings of adoption.

We actually saw GSV growth of 190% quarter over quarter in Q2, and that is at the very early phases. Customers who adopt Business Plus, which is going to have, it’s a premium take-rate product, so it’s double the take-rate on the client side of our normal pricing. Some of our new AI-enablement products, UMA Project Management, other tools like that that will help work get done on platform are going to be part of this Business Plus product. Beyond that, the really interesting future for us is the opportunity for AI agentic work to happen on the platform. What we see is a future where freelancers alongside AI agents are getting work done on the platform. For us, we can charge a take-rate on the work regardless of whether it’s done by a human or machine or both.

Eric, Interviewer: Okay. One follow-up question that’s been talked a lot about at this conference is how companies are deploying AI internally. I know it’s not as much about external and growth and some of the topics we probably will go deeper on, but just are there any examples you can give or ways you want investors to think about the way you’re driving productivity gains or efficiency gains in your own company as a result of AI?

Erica Gessert, CFO, Upwork: Yeah, absolutely. I mean, I think everyone is implementing, you know, kind of AI tools on the backend. Obviously, we’ve, you know, been implementing tools to, you know, increase productivity around coding. We’ve seen about a 25% increase in productivity from our kind of engineering ranks through some of these AI implementations. I’m also seeing some nice benefits within my own organization in terms of starting to implement some of our kind of the LLM models that our teams have built to create natural language search in our own metadata in order to enable more, you know, faster and more rapid analytics internally. There are lots and lots of opportunities there. What we see with these AI implementations, and I think a lot of CFOs are similar in this way, as really productivity improvers, right? I’ve never been at a tech company where the roadmap was completely subscribed.

I think that’s similar for everyone, right? We have roadmaps that we want to execute on, and we are starting to execute faster and seeing faster throughput. It’s really more of a productivity play.

Eric, Interviewer: Okay. You mentioned Business Plus, but I want to maybe go further up the funnel and talk more broadly about Enterprise. You’ve seen a lot of good growth out of the Enterprise. You’re building a lot of Enterprise solutions. Talk a little bit about repositioning the company for the larger enterprises over the long term on the client side.

Erica Gessert, CFO, Upwork: We’ve had some incredibly exciting announcements around our Enterprise business just in the past couple of months. When we reported earnings in August, we announced two acquisitions of a company called BubTea, which is a workforce management platform, and a company called Ascend, which offers a full suite of kind of workforce solutions, staffing solutions. This is a true game changer for us. If you think about our Enterprise business as it’s been in the evolution over the past several years, we have always been the expert and the best in the industry at offering IC talent, independent contractor talent. That’s really only about 10% of very large enterprise wallet spend. We have this tremendous slate of very top-tier marquee enterprise companies in our list of clients.

Up to now, because we were largely offering this IC lit contractual labor, we were only able to access about 10% of the spend. With the addition of BubTea and Ascend, we have access to the full suite of contingent labor products across staffing solutions, employer of record, agent of record, and really the full slate of contingent labor. Now the full wallet of enterprise spend is open to us. I’ll tell you, since we announced our new Lifted entity just about three weeks ago, we’re getting a tremendous number of inbounds, not just interest from our internal customers, but actually RFP requests coming in from other companies out there. It’s a super exciting time for our business.

Eric, Interviewer: Let me just follow up on that. You bought the two companies, you’re integrating them, you’re repositioning. How should investors think about the pathway towards the enterprise solutions being built out, deployed, and you could see the full impact of it from a growth standpoint?

Erica Gessert, CFO, Upwork: Yeah, absolutely. Look, we are, of course, going after now very large kind of contracts. These are really tens, if not hundred million dollar contracts that we’re working, that we’re going after. We’ve been very thoughtful about making sure that people understand that there will be a few quarters of both integration work as well as working through the kind of discussions and negotiations of these contracts. We expect the major GSV and revenue growth coming from these requisitions to start to manifest in the back half of 2026. That said, like I said, we said at the end of last year that we expect to resume both revenue and GSV growth on both the marketplace and the enterprise as we enter 2026, and we’re still well on that track.

Eric, Interviewer: Okay, interesting. Your take rate has continued to move higher and been a tailwind for the company, and advertising in particular has been a bright spot for the company. Talk a little bit about what you’ve built that has had an impact on take rate for the business, looking backwards first, and what are your broad messages to investors about how take rate might evolve on the go forward?

Erica Gessert, CFO, Upwork: Yeah, you know, if you look at our take rate compared to the rest of the industry, we are at the low end today. Our take rate on the marketplace is about 18.5%. Our total take rate is around 19.5%. That really is kind of the lowest. If you look across the industry, staffing industry is going to be around about, call it 30%. Others in the industry are closer to the mid to high 20s. The bias of our take rate is up. We are very, very thoughtful about making sure that we are pricing to value as we continue to grow take rate. People should expect that both GSV and take rate will be growth drivers for us as we enter 2026 and beyond. We have a number of levers that are pushing that. As you mentioned, our ads products continue to grow.

We have a currency called Connect, which is what our freelancers use to bid on jobs. Our Connect revenue continues to grow, grew 20% in Q2 and is continuing on that pathway. We also have our subscription products, like I said, Freelancer Plus. We have also started to just recently, in May of this year, announced or kind of revised our Ts and Cs on the freelancer side to have a variable fee on the freelancer side, anywhere from 0% to 15%, where it had been a 10% flat fee. The purpose of doing that is really to use the supply and demand dynamics on the platform to drive both take rate and GSV. If you think about the way that our kind of categories work, we have some categories with very, very large supply where we can increase take rate.

Other categories with lower supply where we may decrease take rate to grow GSV. We started experimenting with that in May with very, very nice successful results. We are really in the first inning of that work. We see that as a major driver, both of take rate and of GSV going into 2026. Lastly, of course, is our Business Plus product, which is very early days. We see higher spend from the customers who adopt that product. Actually, about 35% of Business Plus users are new to the platform. We haven’t even started to market it yet. A lot of exciting things to come there from a take rate driver point of view.

Eric, Interviewer: One question I do get from investors from time to time is there’s an acknowledgement of that gap in take rate. How do you think about a take rate that’s lower than the industry being a competitive advantage to some degree, as opposed to closing a gap where you feel there’s some economic value that’s being added from a platform standpoint that should be realized? How do you think about that gap? Have you talked about that as a team?

Erica Gessert, CFO, Upwork: Yeah, no, I mean, I think it’s an interesting question. That’s why we’re so focused on pricing the value. I mean, the reality is that as we build out the value prop, if you look at the Business Plus product, what we offer there is access to the top talent on the platform, curation of talent, net 30 billing. We’re actually offering even more features, the ability to build teams more easily, and gather groups of freelancers in order to execute on bigger products. This is opening up more of the kind of medium business TAM for us. As long as we continue on that pathway to pricing to value, we see no reason that it can’t continue to be both a competitive advantage and a growth driver for us.

Eric, Interviewer: Okay, you’ve talked about it a little bit, but beyond core marketplace, I think the other area that’s increasingly getting some focus is what you can build and scale on the value-added services side on a multi-year view. Just thematically bring together how the company thinks about value-added services and sort of what that might do to the platform over the next three to five years.

Erica Gessert, CFO, Upwork: Yeah, sure. I mean, look, I think there’s a tremendous amount of opportunity on the value-added services side that we are just in the very early phases of thinking through and tapping into. We’ve already started, we launched a micro-lending product for freelancers. We can do the same on the client side. There’s really a lot more to come there that we’re, honestly, just at the beginning of our journey on.

Eric, Interviewer: Okay, understood. We talked a little bit earlier about the progress you’ve made on margins. Just one last one here on the cost side. Anything to highlight about the way in which you anchor investors to think about long-term margin potential for the business relative to where you are today?

Erica Gessert, CFO, Upwork: Yeah, I mean, we’ve made tremendous strides on our margin journey. You know, this year I think we’re going to increase our adjusted EBITDA margin 6 points year over year, and we’re incredibly proud of that. We’ve also been able to do that while investing to resume growth in our business. I kind of feel like we’ve been able to do it all. Most of our growth investments that we’ve really kind of initiated over the past couple of years are really showing green shoots right now. Business Plus, our ads and monetization strategies, our enterprise business, all showing growth potential. You will see us start to slow our margin journey because we do want to both grow our margins, continue on that journey, but also, you know, also grow our top line.

You’ll see us as we go into 2026, continue to increase margin, but probably at a slower rate. You know, we reiterated our kind of longer-term goal of 35% adjusted EBITDA margin, no change there. We see that very much within our grasp while also growing top line.

Eric, Interviewer: Okay, building on the margin dynamic, and you talked about it either growth investments or M&A or some of the choices you face as a management team, what are the priorities for capital allocation within the company, and what might change or how have they changed over the last 12-18 months?

Erica Gessert, CFO, Upwork: Yeah, I mean, I don’t know that they’ve changed all that much. We have a very kind of focused set of organic growth investments that we are making, and they are the AI investments that I articulated, the growth of the enterprise, and then our ads and monetization strategies. Beyond that, we’ve had a very successful M&A track record, right? We’ve done four acquisitions in the last three years, two of which were AI tech and talent acquisitions, first Headroom, then Objective AI, both of which have been really the drivers behind our successes of our AI implementations on the platform. Most recently, our two enterprise acquisitions of Ascend and BubTea. We’re super pleased. These have been inexpensive. Ascend and BubTea cost us about a quarter of free cash flow to acquire those two businesses, and they’re going to really be huge growth drivers for our business.

We will continue to look at opportunities for smart, high-yield M&A. Beyond that, we’ll continue to buy back stock and return capital to shareholders as we’ve been doing. We just last week announced our third $100 million stock buyback in two years, and we’re going to continue with that portfolio.

Eric, Interviewer: I know we only have a few minutes left together, but just bring it all together in terms of we’ve talked a lot during this conversation about the strategic priorities, the growth initiatives, elements of margin and capital. If you had to frame what the two or three biggest priorities for the company on the execution side and the roadmap are going forward, what are you guys most focused about? What are you most excited about as a team?

Erica Gessert, CFO, Upwork: I mean, I think I’ve sort of said it all. The opportunities with ongoing implementation of AI on the platform are enormous for us. The fact that we’re seeing this inflection of that category and the growth rate starting to just accelerate is super exciting for us. That’s really only the beginning. Continuing to evolve UMA to become more and more agentic and really help to execute work on the platform and seeing humans and AI side by side executing work is really the future. To be honest, we’re really one of the only platforms out there who are poised to be able to take advantage of this because our DNA is technology. If you think about all the other kind of contingent labor staffing solutions out there, these are very, very old tech stacks that simply don’t have the capability to ingest this kind of technology that we do.

This is enormous for us. Of course, the enterprise TAM, our GSV in enterprise is about $300 million today. The TAM of that enterprise contingent labor business is $650 billion. Accessing that is huge. Third and final, I guess, is our ads and monetization business and Business Plus, which is really our entry into kind of the TAM in the medium business segment. Lots of exciting things to come. I think we’re really, we are in a reflection point in this business. I hope people keep watching.

Eric, Interviewer: Yeah, really interesting stuff. I know we’ll talk in the interim, but hopefully you’ll come back next year and we’ll have this conversation all over again. We’ll check in on all of these things that you’re building and scaling inside the company. Erica, thanks so much for coming to the conference. Please join me in thanking Upwork for being part of the conference this year.

Erica Gessert, CFO, Upwork: Thanks, Eric.

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