1,008: Managing Change and Ensuring Stability | Erica Gessert, CFO, Upwork

Michael O’Grady’s finance strategic moment occurred in 2014 at higher-ed tech company Ellucian. Faced with transitioning from a traditional perpetual license model to a SaaS one, he identified the need for a unified approach across all business functions. Recognizing that the company’s executives had differing visions, he proposed skipping the annual budget process to focus on a 5-year integrated plan. This comprehensive strategy, developed with input from all departments, required significant investment but also was crucial for the company’s transformation. The plan’s success ultimately contributed to Ellucian’s acquisition by TPG for $3.5 billion, demonstrating the power of cohesive strategic financial planning. Read More   O’Grady’s journey to becoming a finance executive was far from linear. In his early years, he was uncertain about his career path. He had a passion for languages, which led him to work for Berlitz, the global language education company. Fluent in three languages, he found that his experience at Berlitz broadened his perspective and honed his communication skills. Still, something was missing. Increasingly, O’Grady found himself intrigued by the complexities of business and finance. He decided to pursue further education in the latter, where his analytical mind and problem-solving skills began to shine. His first major career step in finance was at a midsize manufacturing firm. Here, he encountered the realities of budget constraints and resource allocation, learning the critical importance of aligning financial goals with broader company strategies. By the time he joined Ellucian, O’Grady had built a wealth of diverse experiences that had shaped his financial acumen. His ability to integrate different departmental visions into a cohesive financial strategy helped not only to transform Ellucian’s business model but also to self-validate his growing ambitions to become a CFO.

Two-and-a-half years ago, CFO Tony Querciagrossa began a discussion with Dale Schwartz, founder of Pinstripes, that would eventually lead to Querciagrossa joining the experiential dining up-and-comer as CFO. Turn back the clock a little, and you would see that Pinstripes, aiming for a traditional IPO, had engaged Goldman Sachs to solidify its path toward benefiting from a permanent capital structure. However, the emergence of the omicron variant of you-know-what disrupted these plans, placing the firm’s IPO on hold as uncertainty loomed. Read More Despite the sudden challenges, Pinstripes pivoted swiftly to seize the opportunity presented by a changing financial landscape. Enter Banyan, a SPAC deeply invested in the industry and eager to collaborate. Querciagrossa joined the company just as the Banyan team was finalizing their business combination agreement—which would mark a pivotal moment in Pinstripes’s trajectory. With momentum building, Querciagrossa stepped into his role as CFO during the second phase of Banyan’s road show, where discussions revolved around securing vital capital for the company’s future. For the sake of perspective, it may be informative to note that Querciagrossa’s journey had begun at GE, where he honed his skills as a proactive finance executive amidst a culture that encouraged strategic thinking over reactive responses and prepared him well for his critical juncture with Pinstripes. His experience in navigating complex financial landscapes and fostering growth in dynamic environments would serve as a foundation for his leadership role at his new firm. Embracing the challenges presented by the SPAC route, Querciagrossa tells us, he nonetheless was fortunate to be able to achieve the the agility and foresight necessary to navigate turbulent market conditions and steer Pinstripes toward its next phase of growth.

On Location IMA24 (San Antonio, TX) the annual America's conference for the Institute of Management Accountants (IMA)  CFO Thought Leader Host Jack Sweeney speaks to Mike DePrisco, IMA President and CEO, about the evolving importance of certifications like the CMA (Certified Management Accountant) and the newly established FMAA (Financial and Managerial Accounting Associate) to support early-career individuals. DePrisco stressed the need for personalized professional development to cater to unique career motivations and the critical role of CFOs in promoting continuous learning. The IMA is focusing on stackable digital credentials in areas like AI and cybersecurity to help professionals specialize further. Additionally, the IMA plans geographic expansion, notably into Japan, and aims to strengthen partnerships with academic institutions and organizations. Dianna Steinbach, IMA SVP growth, highlights the opportunities for growth both domestically and internationally, with a strategic push into Japan due to its need for financial management and analysis (FP&A) resources.

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.

When she was an international studies major living abroad, Ashley Johnson tells us she met a U.S. ambassador whose unvarnished career advice subsequently led her to divert her career path away from the diplomatic corps of the U.S. foreign service. Johnson reflects, "I thought I was going into the State Department." However, a weekend spent with Ambassador Roy Huffington, immersed in discussions about the pivotal role of a strong economy, sparked a profound realization. "You cannot be an effective leader if you don't understand how to make a strong economy," the ambassador and renowned Texas oilman emphasized, leaving Ashley determined to delve into the world of business and finance. More encouragement followed when a friend from a study group introduced her to the intricacies of Wall Street, igniting her fascination with financial statements. "Financial statements tell a really interesting story," she notes, "and if you know how to read them, you're going to understand something about that company that maybe other people won't." Johnson routinely draws our attention to lessons and moments of insight, such as when she illustrates for us the origins of her unwavering commitment to thorough analysis. During a pivotal investment decision, her scrutiny of financial assumptions saved her firm from a potential catastrophic loss. "Look for those assumptions, question them again and again," she advises, emphasizing the critical role of meticulous examination in financial decision-making.

In this episode of Controllers Classified, host Erik Zhou is joined by Eugene Spevakov, Treasurer and Head of Corporate FP&A at 6sense. The conversation begins by tracing Eugene’s path, highlighting his start in civil engineering and his transition into treasury and corporate finance. The episode then dives deep into the primary responsibilities of a treasury function: cash and risk management (aka, you need to be able to move money from point A to point B safely). Eugene spends time explaining what both mean and best practices associated (tip: prioritize cash preservation, liquidity, then yield). As a part of that, he reflects on the SVB collapse a year ago, and how that galvanized a lot of companies to take a hard look at their cash and risk management processes. The conversation pivots to Eugene’s focus areas and accomplishments at 6sense. He shares how he built the company’s first official treasury function, executed a senior secured credit facility, and designed an investment portfolio to optimize yield and reduce banking fees. As a part of this, he spends a few minutes on the macro environment, including the end of the ZIRP era and the influence of geopolitics. His primary point? Manage the risk you can control, and scenario plan for what you can’t. This is a “don’t miss” episode for finance leaders looking to build effective cash and risk management strategies.

CFO Jorge Stevenson’s finance career journey begins in Santiago, Chile, where both his parents were leaders within the business community and instilled in him the importance of finance when it comes to  achieving business success. Jorge’s formal business education began with an MBA from Duke University, where he honed his finance. His professional journey includes pivotal roles at a number of different organizations. At Goldman Sachs, he gained exposure to mergers and acquisitions, financial planning, and board-level responsibilities. His tenure at Prudential further solidified his strategic thinking capabilities, working on mergers and acquisitions across Latin America, Europe, and Africa.

In the early years of Scott Henderson’s career, the dotcom bubble burst, leaving the tech industry in turmoil and many young professionals uncertain about their futures. Despite this chaotic climate, Henderson decided to take a calculated risk by joining another dotcom venture. This time, the company was a modest enterprise with 300 employees and $25 million in revenue. At the time, it was known as Salesforce.com. Henderson’s gamble paid off handsomely. As Salesforce grew from a promising start-up into a global tech giant, Henderson’s role within the company expanded significantly. He ascended through the ranks, eventually managing a team of 600 people across 13 countries. During his tenure, he played a pivotal role in integrating major acquisitions like MuleSoft and Tableau, helping to navigate the complexities of these integrations while driving corporate planning and strategic initiatives. In 2022, Henderson took on a new challenge as CFO of DISQO, a brand experience platform company. Stepping into DISQO, he was greeted by a smaller team and the economic headwinds of a post-pandemic world. Henderson immediately set about understanding the company’s structure, focusing on areas for improvement and leveraging his extensive experience to bolster DISQO’s finance operations. One of his key initiatives was to enhance Revenue Operations (RevOps), positioning it as the crucial link between the front and back offices. This strategic focus helped DISQO to navigate economic uncertainties while preparing for durable growth. Under Henderson’s guidance, DISQO transformed its finance function into a strategic partner, enabling better decision-making and fostering a culture of continuous improvement. Henderson’s career journey, marked by calculated risks and strategic foresight, underscores the importance of adaptability and vision in the ever-evolving tech landscape.

Efraín Pérez Agosto began his career on the lively casino floors of Puerto Rico, where his fascination with the gaming industry was first sparked. Starting with a succession of jobs, he quickly showcased his analytical prowess and passion for finance. In search of broader horizons, Agosto relocated to the U.S. when his casino owner set down roots in Indiana. This move marked a pivotal chapter in his career, as he balanced work while completing his undergraduate degree stateside before going on to pursue an MBA. The Indiana operation offered Agosto invaluable experience in the American gaming market. His ability to dissect complex data and drive strategic initiatives began to set him apart. During this period, Agosto tells us, his pursuit of an MBA expanded his strategic thinking and prepared him for more significant challenges ahead. Upon graduating, Agosto joined Caesars Entertainment, where he soon found himself on a fast track to becoming a casino controller. After 4 years with Caesars, it was then on to MGM Resorts International, which was seeking to field a finance team for its new National Harbor resort in Maryland. Agosto headed east, where over the next 5 years he steadily advanced up MGM’s finance ladder. Eventually having beefed up his FP&A resume, he subsequently landed inside the National Harbor’s CFO office. Although his leadership there was notably tested by both the COVID-19 pandemic and a significant cyberattack, his proactive and resilient approach was able to help to safeguard the business. Today, Agosto focuses on driving growth initiatives and navigating labor market challenges, positioning him as a transformative finance leader in the gaming industry.