Speakers

Hayden Brown is president and CEO of Upwork, the world’s human and AI-powered work marketplace, where Fortune 100 companies through small businesses and highly skilled independent professionals from 180 countries connect and work together. Hayden joined Upwork in 2011 as a product manager and held roles running Upwork’s marketplace business, as chief product officer, and as chief marketing officer before being named CEO in January 2020.

Hayden is driven by her passion for delivering on Upwork’s purpose to create opportunity in every era of work. Under her leadership, Upwork has vastly expanded its product portfolio, and today, she is animated about leveraging cutting-edge technology, including AI, to make work easier and more delightful for businesses and professionals alike. Most recently, she oversaw the introduction of Uma, Upwork's Mindful AI, a powerful AI work companion designed to help businesses and freelancers every step of the way across the Upwork experience.

During her time with the company, Upwork has grown from $10 million to more than $750 million in annual revenue, and from $100 million to more than $4 billion in annual client spend. Upwork’s workforce, now numbering more than 2000 team members, has always been made up of approximately 75% freelancers working remotely from around the world on the Upwork platform.

After receiving an AB in politics at Princeton, Hayden started her career at McKinsey and Company as a business analyst, where she fell in love with tech. She joined Microsoft’s online strategy team and later the company’s corporate strategy group, before starting the corporate development function at LivePerson, and eventually joining Upwork (then oDesk). She has been named to Forbes’ Future of Work 50 and SIA’s Staffing 100 North America lists, and was at the helm when Upwork was named one of TIME’s Most Influential Companies as well as one of Fast Company’s Most Innovative Companies.

When she’s not working remotely from somewhere new, she resides in the San Francisco Bay Area with her husband and two children.‍

Erica Gessert is Chief Financial Officer at Upwork, where she oversees Upwork’s global finance team and operations.

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

Erica studied economics and philosophy at Reed College.

Andrew Rabinovich is Chief Technology Officer and head of artificial intelligence (AI) & machine learning (ML) at Upwork, where he leads all aspects of the company’s transformation to compete in the age of AI.

Andrew has been studying machine learning with an emphasis in computer vision and multimodal AI for over 20 years. He has authored more than 100 peer-reviewed publications and patents. Andrew worked for years in R&D leadership positions at Google. In 2015, he joined the preeminent AR company Magic Leap as head of AI, focused on perception and human-centered AI for mixed and augmented reality. In 2020, Andrew co-founded Headroom, an AI-powered video conferencing platform. In 2023, Headroom was acquired by Upwork, with Andrew and the Headroom team joining the company.

Andrew holds a Ph.D. in computer science from University of California San Diego.

Dave Bottoms leads Upwork's Marketplace organization, a global team responsible for the core Talent Marketplace, search & discovery, ads & monetization, core mobile experiences, as well as new product innovation. Functional oversight includes Product Management, Product and Growth Marketing, Engineering, and UX - Design and Creative.

Dave brings more than 20 years of experience in Silicon Valley 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 the Homepage, News, Sports and other core media experience.

Dave holds a BA in English Literature from Denison University.

Peter Sanborn is Vice President, Strategy, Corporate Development and Partnerships at Upwork, where he oversees Upwork’s corporate strategy, M&A and investing activities as well as business development and channel partnerships. Peter has nearly 20 years of experience across strategy, M&A, investing and finance roles.

Prior to joining Upwork he was a General Partner of Arbor Ventures, focusing on early and growth-stage investments globally across fintech, payments and commerce enablement. Before Arbor, Peter served as Vice President, Head of Corporate Development at PayPal and Managing Partner of PayPal Ventures. Previously, Peter held strategy, M&A, finance and investor relations roles at HSBC in Hong Kong and Mexico City.

Peter holds a BA in Economics and International Studies from Northwestern University.

Ernesto Lamaina is the General Manager of Lifted, an Upwork company dedicated to helping enterprises source, engage, and manage contingent talent across every contract type—independent contractors, staff augmentation, Employer of Record, and managed services.

At Lifted, Ernesto leads strategy, product, and operations for the business, driving innovation in workforce solutions that combine technology, compliance, and talent access to meet the evolving needs of global enterprise clients.

Before launching Lifted, Ernesto led Upwork’s global enterprise and managed services business, building the foundation for the company’s expansion into the broader contingent workforce market. Earlier in his career, he served as CEO of Adia, a digital staffing platform connecting talent with temporary work opportunities worldwide.

Ernesto holds a Master’s degree in Business and Finance from Università Carlo Cattaneo – LIUC.