TTV Global Corp

Driving Innovation With AI: A Q&A With Upwork’s Head of AI & Machine Learning Andrew Rabinovich


Generative AI continues to develop and advance, and is reshaping the work landscape. The transformative impact the technology is having on professionals and industries alike is only now beginning to be seen. AI is supercharging productivity and efficiency and helping to get mission-critical work done.

Upwork is on a journey to become the preeminent destination for AI-powered talent and work, and we are thrilled to welcome Andrew Rabinovich to our team. Andrew is one of the world’s leading scientists in deep learning and computer vision research, and he leads our artificial intelligence (AI) and machine learning (ML) team.

Andrew came to Upwork with two decades of experience in AI/ML, having spent seven years at Google and five as the head of AI at Magic Leap. Most recently, he co-founded and served as the CEO of Headroom, an AI-powered video conferencing platform that Upwork acquired at the end of 2023.

We spoke with Andrew about his decision to join Upwork, how he’s thinking about AI’s impact on the work category, and why he plans to infuse every interaction on Upwork with human-centered AI.

After spending two decades in the AI/ML space, you could have worked at almost any company you liked. What led you to choose Upwork?

The work category as a whole is rife with opportunity for technology like artificial intelligence to reshape the industry. I envision a state in which businesses and independent professionals can incorporate AI seamlessly into their workflows and scale their productivity exponentially.

In my previous role leading Headroom, we were building a future of work platform. The idea was to make people more effective and productive in their collaboration via AI-powered videoconferencing. My role with Upwork is very much an extension of my previous work and I’m excited to take my years of knowledge in the AI space and bring them to an already thriving marketplace.

Upwork is the world’s largest work marketplace, which I think presents a unique advantage. It’s a self-contained labor market for independent talent that is backed by more than two decades of data and insights from a full range of hiring and work behaviors. That’s millions of data points that can be used to create human-centered AI that will help power all the connections happening across the Upwork marketplace. Through AI, we can make collaboration between businesses, established and startups alike, and professionals even better.

AI will truly unlock work for people and businesses, making it seamless. We will no longer need to worry about mundane “busywork” but will be able to truly focus on work that requires human ingenuity and creativity … creative work!

You used the term “human-centered AI” rather than generative AI. Why is that? What’s the distinction there?

Humans are a crucial part of the future of AI. When we say “human-centered” we are referring to creating AI systems that amplify and augment rather than displace human abilities. Human-centered AI seeks to preserve human agency in a way that ensures artificial intelligence meets our needs while also operating collaboratively, delivering equitable outcomes, and respecting privacy.

What are you excited about building at Upwork?

To put it simply, I want to power every interaction on Upwork with AI. I want to make us—from our core product all the way down to our infrastructure and data—faster, more efficient, and more productive. Ultimately, this will help us continue to improve the services we provide to the professionals and businesses that use Upwork.

When I joined Upwork, I quickly saw that our perennial focus is driving innovation on behalf of our customers. I think a lot of that innovation will come from continuing to embed AI into the core Upwork marketplace.

AI isn’t new to Upwork; the team has already yielded some exciting product developments like proposal tips, Upwork Chat Pro, and job post generator. I want to guide the team in continuing to improve on these products and make the experience for clients and talent more intuitive and even more seamless.

Two specific areas I would call out are search & discovery, and using our platform as a companion. Successfully matching freelancers looking for work to clients looking for help lies at the heart of the core problems we solve for customers, and AI has the ability to further enhance the relevance and speed of these matches.

We can also build upon Upwork Chat Pro and create an even more powerful work companion that is backed by decades of data. For example, the work companion of the future will work alongside you on projects and can proactively talk strategy and understand what you need before you ask. I envision a world in which artificial intelligence—and generative AI in particular—makes the ways we interact and work together more human, creative, productive, and secure.

A final point I’ll make is that I believe we should empower talent with access to the best AI tools, apps, and resources so the professionals using our marketplace can be more productive, earn more, and deliver better outcomes for clients. The right AI tools—and know-how—drive positive feedback loops. Our goal is to ensure that, no matter the project, Upwork will be the best place for talent to discover and understand how to use the ideal tools for their work.

What do you think will separate the companies that win in the current age of AI?

Companies that are going to win this age of AI have what I think of as a moat—a way of producing lots of new data. In the past, many forms of generative AI were trained on open source data domains like Wikipedia or Stack Overflow.

Algorithms used to be the moat, or the secret sauce, because while everyone worked on the same public data, the company that created the best algorithms won. The industry is quickly changing and now everyone publishes their algorithms publicly, so it’s less important. Today, the data is what really matters and will make the difference.

Upwork is in a prime position to be successful because of the tremendous amount of data we have as the leading independent marketplace for over two decades. I’m excited about our ability to continue connecting businesses with freelancers and getting more projects completed, at even greater speeds and more efficiently than ever.

Lightning round! What’s your favorite AI-related movie?

Her! The movie is from about 10 years ago and stars Joaquin Phoenix. I thought it offered a very thought-provoking exploration of human-AI relationships, presenting a more nuanced and realistic portrayal of what the future could look like. It’s not perfect and it’s just a movie, but I thought it was ahead of its time.

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

Embrace a mindset of lifelong learning and adaptability. This is especially crucial in the rapidly changing field of AI, where staying abreast of the latest developments is so important. I’m often solving problems that don’t have obvious answers. Continuous learning not only keeps my skills sharp but also positions me to navigate the dynamic landscape of technology effectively.

Finally, what is one thing you can’t live without?

I would list two things: music and curiosity. You’ll often catch me with my headphones on while I work. And curiosity drives my personal growth and intellectual development. It acts as a catalyst to discover new ideas, perspectives, and possibilities. Without curiosity, the motivation to learn and adapt diminishes, hindering one’s ability to navigate an ever-changing world.