Dave Bottoms leads Upwork’s Marketplace organization, a global team responsible for the core Talent Marketplace, search and discovery, ads and monetization, core mobile experiences, as well as new product innovation and analytics.
Dave brings more than 20 years of Silicon Valley experience to Upwork. He joined the company in 2022 from Meta, where he led the Ads Manager Platform and Experiences team, responsible for the flagship enterprise product used by millions of small businesses and global advertisers to drive valuable business outcomes across Facebook and Instagram. Prior to Meta, Dave led the self-service customer growth team at Dropbox and multiple product teams at Yahoo!, including those for the Homepage, News, Sports, and other core media experiences.
Upwork began over two decades ago by pioneering a better way of working, helping businesses find more flexibility and connecting talent with more opportunities.
Upwork, a 20-year-old platform, is undergoing significant transformation under your leadership. What are the challenges and opportunities in driving innovation in such a well-established company?
It’s an exciting time to be at Upwork as we’re both driving a transformation across our products and platform, as well as leveraging AI tools to change how we work and build new capabilities and workflows. In many ways, we are a mature, public company who’s operated through various incarnations and adoption cycles, but the new age of advanced machine learning and generative AI has been a tremendous boon to innovation and product solutions we’re able to deliver to our customers.
As with any major technological shift and especially during this period of AI expansion, challenges and opportunities emerge as new capabilities are born. At Upwork, we see AI as a force-multiplier for our platform and for the talented professionals who use it not only to augment work for clients – whether that’s coding, marketing, research or design – but also in getting started on that work faster. It’s also an accelerant for the businesses on our marketplace that are finding talent to drive to their true business outcomes more quickly.
One challenge is ensuring that the integration of AI into our products addresses real and substantial customer problems. We’re not just building or adding new features for the sake of providing something “new,” but truly leveraging the power of various AI models to drive increased efficiency and solutions for the freelancers and businesses that use our platform everyday. Fortunately, we are in an advantageous position to drive these outcomes with AI tools because of the tremendous amount of high-quality signal –from real-time behavioral data to rich, historical data – that we have amassed from a diverse range of specific work delivery that goes back many years. We’re using this data to train our custom large language models (LLMs), power many of our latest product experiences, and deliver the best work outcomes for our customers.
With your extensive experience at Meta, Dropbox and Yahoo, how has your approach to product management evolved? What lessons have you carried forward to your current role at Upwork?
My approach to product management has evolved to emphasize a balance between user-centric design and scalable innovation. There aren’t many places better than Meta for learning how to build products at scale and for a diverse range of users – Facebook and Instagram have billions of active daily users! In my role leading product for the Ads Manager Platform and Experiences team, I learned how to manage global, cross-functional teams building products that cater to both small and medium-sized businesses as well as large global agencies supporting Fortune 100 enterprises.
Additionally, my experiences at Dropbox and Yahoo were crucial in helping me develop a deep understanding of product-led growth mechanics for SaaS solutions, as well as content personalization and how to balance “big bets” across a portfolio of consumer media products. Both roles required a holistic understanding of product strategy and development from new product concept prototyping to launch and driving consumer adoption. I learned how to ship products and manage the teams that built those products.
Now at Upwork, I have the benefit of drawing on the last 15-years of Product Management experience to guide and steer innovation at a company that is reshaping the future of work. Without a doubt, the biggest challenge is how freelance talent and small to mid-sized companies grapple with how best to embrace and adopt the AI technology wave.
Across my previous experiences, I’ve seen some seismic technological shifts like the one we’re now seeing with AI –from the rise of social media to the shift to smartphones and the need for products to be mobile-first. While big technological shifts can mean big changes, at its core product development continues to be about doing one thing consistently well – solving customer problems. With the rise of AI, technological advancements are providing a huge opportunity to reinvent Upwork products so that businesses and talent work better together and produce stronger results. We’re starting to realize some early wins with our recent release of Uma, Upwork’s Mindful AI.
How do you balance making small, medium, and big bets in AI product development, especially given the rapid evolution of AI technologies? Could you share an example of how this strategy has been implemented at Upwork?
AI product development requires a strategic blend of experimentation, scalability, and long-term vision. One core framework that I use in product planning that has been helpful in developing AI products at Upwork is what I like to call a VC-approach to product development, where I’m balancing a wide-range of portfolio products. About 40% of what my team is working on is big rocks or big bets that can have a very large impact on the business, but also are bigger risk items and take a considerable amount of time. The remaining 60% is split in half on near term items that I have high confidence the team will execute against the plan on, but likely won’t have a major ROI for the business and the other 30% is product work that keeps the lights on like fixing bugs. AI at Upwork is a big bet for us. It’s difficult from a development perspective requiring a high level of expertise, but the benefits can be massive and so we’ve allocated a healthy portion of our product focus to this area of work over the last year.
We launched job post generator, which is now powered by Uma, Upwork’s Mindful AI, towards the end of last year as an example of a “big bet” product that came about through a process of experimentation from our in-house product incubation team, Upwork Labs, and scaled into a viable solution. With the rise of generative AI last year, the team explored a myriad ways to help our customers take advantage of the opportunity the new technology presented. We knew that clients often encountered the obstacle of starting with a blank page when describing their work needs. As such, we set out to determine how we could use generative AI to overcome this challenge. Last year, we announced a major expansion of our AI offerings including the launch of job post generator, which is an AI-powered generator of a job post that helps clients get a job post drafted in seconds.
How does Uma, Upwork’s Mindful AI, differentiate itself from other AI solutions on the market, particularly in terms of enhancing the hiring and matching process for businesses and freelancers?
AI models are only as powerful as the data that they are trained on. Uma is built on top of industry-leading large language models (LLMs) and customized with Upwork platform data, and it’s this customization that differentiates it from other AI solutions in our industry. Today, Uma powers a number of key experiences in the hiring and matching process that are critical to clients and freelancers discovering each other, getting started, and completing more high-quality work. We’re able to enhance these work actions because we have access to 20+ years of data, trillions of tokens of specific and highly relevant data from our two-sided marketplace that encompass a wide range of work interactions. Uma learns off these data points to serve as a constant, intelligent companion for our customers, helping businesses and freelancers every step of the way across the entire Upwork experience.
With features like Best Match insights and Upwork Chat Pro, how is Uma specifically tailored to help freelancers stand out and secure more projects? What feedback have you received from freelancers during the beta phase?
Powered by Uma, Best Match insights help businesses find the best potential person for their job quickly by identifying relevant insights like top proposals, client reviews, and skill alignment with a job post. From the freelancer’s POV, it specifically highlights projects that closely align with a freelancer’s skills and preferences therefore increasing their chances of being noticed by potential clients and finding work that best fits their expertise. With Upwork Chat Pro, Upwork’s work companion powered by Uma, freelancers have a dedicated chat app that helps them solve challenging tasks, boost productivity, and do their best work.
We’re excited about the progression of these key experiences and found that during early releases freelancers reported increased visibility and more targeted project matches, leading to higher engagement and success on our platform. Just this past quarter, daily active users of Upwork Chat Pro grew 68% quarter-over-quarter, and we’re seeing freelance professionals starting to land more work and earn more as a result.
How do you envision the future of work evolving over the next decade, particularly with the integration of AI and emerging technologies?
It’s hard not to see a future, at least in the near term, where AI becomes more and more embedded in our day-to-day work and lives. Businesses and professionals will continue to incorporate AI into their workflows and this will lead to increased productivity. It’s important to note that humans remain a crucial component of this future. As AI increasingly handles routine tasks and provides valuable insights on command, professionals will become faster, more efficient, and be able to do more. Jobs and skills will naturally evolve, as they do in most technological shifts. While some jobs may change or fade, many others will emerge, compelling humans to adapt. We are already seeing many traditional roles being transformed by automation, necessitating upskilling or reskilling, while new opportunities are arising in areas that complement AI, such as data annotation, curation, and AI security, to name a few. Humans will increasingly focus on tasks requiring emotional intelligence, creativity, critical thinking, and complex problem-solving—areas where human ingenuity excels. With AI taking on routine tasks, we will have the latitude to tackle more intricate, strategic, and pressing challenges within our organizations. It’s an exciting future and I’m proud to be at a company that is leaning in and leading at the forefront of its industry when it comes to AI.
Thank you for the great interview, readers who wish to learn more should visit Upwork.
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