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 into full view the path leading beyond the crisis.
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.
Read MoreIn May 2022, Gessert was named CFO of Upwork. At the time, the company was grappling with profitability challenges despite 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 a few quarters, she has led Upwork to a turnaround, achieving 18% EBITA 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 has implemented predictive churn models and other analytical tools to gain deeper insights into customer behavior, significantly improving Upwork’s client growth.
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CFOTL: Tell us about Upwork … what does this company do, and what are its offerings today?
Gessert: Upwork is the world’s work marketplace. We are the largest online marketplace for companies seeking to find independent professionals and for professionals trying to find work. No one has our sizing scale, as we do over $4 billion on our platform every year. We serve a very large and growing client base of about 872,000 on our platform, helping all to fulfill their essential work needs.
Read MoreWe went public about 5 years ago. We raised about $360 million in convertible debt in August 2020 and have $100 million to $150 million in cash, so we have a very strong balance sheet. The other really important point to understand about our business is that when I came on about a year ago, we were actually not profitable as a business. I think that the company made decisions to invest in the benefits to the business of the shift to remote and other things like that when there were tailwinds because we were and are all about connecting businesses and professionals to get work done remotely. This was the case during the pandemic, certainly, but not necessarily so to the same extent afterward. So, with interest rates being where they are and with the kind of nervousness in the market last year, it was really important that we move to profitability—which we’ve done very, very rapidly. We gained 20 points of EBITA down margin in just three quarters last year and have just recorded 18% EBITA margins in the first quarter of this year, so now we’re cash flow–positive. We’re going to be regrowing our cash balances each and every year, and this has so far actually enabled us to buy back about $100 million worth of stock. jb
“When it comes to developing new ways of working and new ways of getting things done, full-time employees tend to be a lot slower than our talent base of active freelancers. So, we’re now very focused on making sure that our talent base is the most AI-enabled talent base in the world. With regard to advice, it’s three things: Trust your instincts. Build a great network. Hire the best.” –Erica Gessert, CFO, Upwork
Upwork | www.upwork.com | San Francisco, CA