In the throes of the Great Recession, Erica Gessert faced one of her first tests of leadership. As the head of Investor Relations for Virgin Mobile, she found herself navigating the collapsing financial sector. Key banks that were integral to the company's operations began to crumble, and the economic landscape was fraught with uncertainty. Keeping investor concerns top of mind, Gessert was able to help steady Virgin Mobile and bring the path leading beyond the crisis into full view.

In the years ahead, Gessert’s career trajectory continued upward as she transitioned into various finance leadership roles. She spent a significant portion of her career at PayPal, where she honed her skills in analytics and strategic planning. Her ability to leverage data for decision-making allowed her to emerge as a strategy-minded finance executive capable of driving business growth and profitability.

In May 2022, Gessert was named CFO of Upwork. At the time, the company was grappling with profitability challenges despite the favorable tailwinds from the pandemic-induced shift to remote work. Drawing on her experience, Gessert initiated a series of strategic measures to stabilize the company's finances. Within just three quarters, she led Upwork to a turnaround, achieving 18% EBIT margins and positive cash flow.

A key aspect of Gessert’s strategy has been leveraging technology and data analytics to enhance customer acquisition and retention. She implemented predictive churn models and other analytical tools to gain deeper insights into customer behavior, significantly improving Upwork’s client growth.