CFO THOUGHT LEADER CFO THOUGHT LEADER

Beginning her career as an analyst, Carol Lee honed her technical skills both in pre-revenue start-ups and a multinational corporation with over $10 billion in revenue. These contrasting environments, she tells us, equipped her with a unique perspective on what it takes to be both scrappy and scalable.
Early in her career, Lee immersed herself in M&A activities, gaining insights from both the buy and sell sides. As an analyst, she was able to absorb vast amounts of financial information and build detailed models as she observed high-stakes negotiations from up close. These experiences were instrumental in understanding the end-to-end processes of M&A, from financial scrutiny to integration and synergy realization. This comprehensive view became invaluable to her as she emerged as a finance leader.
Lee’s tenure at 100-year-old Konica Minolta exposed her to large-scale operations and the intricacies of synchronized business processes. This period taught her the importance of structured, efficient workflows and the necessity of diverse go-to-market strategies. These insights became crucial when she transitioned to the fast-paced environment of Silicon Valley tech start-ups, where agility and rapid decision-making are essential.
In her first CFO role at GoodData, a VC-backed company, Lee embraced the chaos and speed of the start-up culture. Her ability to balance structured financial oversight with the need for flexibility and rapid experimentation became a hallmark of her leadership. This balance, coupled with a deep understanding of various business scales and sectors, defines Lee’s CFO mindset today.
Lee emphasizes the importance of communication, storytelling, and partnership in finance leadership. By integrating technical acumen with strategic foresight and a collaborative approach, she navigates the complexities of scaling businesses while fostering innovation and growth. 

 




CFO Thought Leader host Jack Sweeney and performance management guru Brett Knowles explore and highlight the takeaways from The 20 Leading CFOs of AI report, recently published by CFO Thought Leader. The conversation underscores the ethical challenges posed by AI and the critical role CFOs play in ensuring responsible governance. Notable examples like Krishna Rao of Anthropic and Colette Kress of Nvidia. As AI continues to revolutionize industries, CFOs are tasked with balancing innovation and ethical stewardship.

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.
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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.
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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.