CFO THOUGHT LEADER

Matt Ostrower remembers losing sleep over a decision that carried consequences for employees, lenders, and shareholders.
At Site Centers, Ostrower tells us, the management team was confronting two challenges. Investor fears about the internet’s impact on retail real estate were depressing stock and bond valuations. Then Hurricane Maria struck Puerto Rico, leaving a portfolio of company assets out of commission for months.
The immediate pressure was to reopen properties and navigate the crisis. But Ostrower says the team forced itself to “pull back” and consider how the company could emerge positioned for growth.
Working with CEO David Lukes and capital markets leader Conor Fennerty, Ostrower says the team developed an answer that had not been executed repeatedly elsewhere: Separate the portfolio, create a liquid pool of assets for public-market investors, and establish a remaining company positioned for greater growth.
Because the approach was untested, Ostrower says the team had no certainty about how investors would respond. “I had sleepless nights for months,” he tells us, describing the market’s acceptance as an “existential question” for the company.
According to Ostrower, investors ultimately embraced the decision, and the strategy received positive press. He says it allowed the company to realize value in one place while setting up another company for growth.
For Ostrower, some of finance’s strongest strategic moments emerge during crises, when leaders are tempted to pursue whatever is most expedient. His experience suggests another possibility: Use the pressure to step back, ask harder questions, and make the decision that addresses not only the immediate disruption but also the company that must exist afterward.

Andrew Korn tracks growth first. EliseAI had surpassed $200 million in annual recurring revenue when he spoke with us, and Korn tells us the company had maintained year-over-year growth above 100% throughout his four and a half years there—“correlation, not causation,” he adds.
That growth gives finance a clear assignment. According to Korn, EliseAI monitors gross margins and burn while ensuring its spending remains prudent and directed toward investments capable of moving the business forward.
The company operates in housing and healthcare, two industries Korn describes as representing about 40% of U.S. GDP combined. He tells us both depend heavily on labor while contending with regulation and legacy technology. The result is overwhelmed teams, administrative work, and consumers waiting too long or paying too much for essential services.
EliseAI enters primarily through the communication layer. According to Korn, its technology handles communications and repetitive work around the clock while providing accurate, compliant answers to renters, residents, prospects, and patients.
But awareness of AI has also created a different challenge. Korn says customers increasingly arrive interested in the technology, yet EliseAI must ensure they understand what they are adopting. The objective is not AI “just for AI’s sake” or something a company can place on its website.
Instead, Korn tells us, AI must improve operations, performance, and business capabilities in tangible ways. EliseAI therefore tracks leases, occupancy, rent collection, maintenance requests, resident renewals, patient calls, and scheduled appointments.
For Korn, the technology earns its place when customers can recognize its impact in the work being completed and the results being produced.

In April 2020, Laura Miller stepped into her first CFO role at Pampered Chef. According to Miller, she was pregnant with her second child, working with a new CEO and joining an executive team that had never worked together in the building before the pandemic sent everyone home.
Demand was anything but predictable. Miller tells us that Pampered Chef’s independent consultants could hold parties online while consumers, confined to their homes, purchased kitchen equipment and looked for ways to earn money. That summer brought a business boom—and immediate pressure on working capital, supply chains and forecasting.
Miller says the company quickly replaced its rolling forecast with a daily forecast. One of her first CFO assignments was determining what would happen if the warehouse could not remain open as an essential business. Finance modeled scenarios “from zero to quadruple” while weighing when to continue accepting orders, when to stop, and how to manage back orders without overwhelming the business.
The professional challenge unfolded alongside a personal one: Miller tells us that she had her baby in June. Navigating both made the period “the fastest crash course into being a CFO.”
The experience also overturned much of her preparation. Miller says she had spent “16, 18 months prepping and planning to be a CFO,” yet none of the issues she had anticipated became her greatest challenges after taking the role.
Her lesson emerges from that collision between preparation and reality: the CFO’s work is not simply executing a carefully developed plan. Sometimes it means rebuilding the forecast daily, considering outcomes at opposite extremes and learning the role while the conditions surrounding it continue to change.

In the early months of Francisco Partners, Samantha Greenberg sat in a room on folding chairs with the firm’s cofounders and one other colleague, planning the business.
According to Greenberg, the private equity firm was pursuing an idea that many considered impossible in the late 1990s: executing leveraged buyouts of technology companies. Greenberg tells us she was drawn to the vision because it challenged the belief that technology businesses could not be predictable or capitalized with debt.
During the firm’s first year, Greenberg says, the team closed its first fund. She helped build operating processes, worked on the first transactions, and participated in fundraising—experiences that she says made her a better operator years later.
That builder’s instinct eventually pulled Greenberg away from investing. After 18 years as a technology investor, she had come to appreciate the discipline of “separating signal from noise,” surfacing insights, and allocating capital. But Greenberg tells us that running her own hedge fund revealed something more personal: She found operating more engaging than investing because it gave her “a seat at delivering the value creation.”
She became a CFO in 2021 and deliberately chose an earlier-stage company instead of a more mature organization. According to Greenberg, the decision allowed her to develop the skills she lacked—leading finance transformation, implementing systems, driving operational maturity, and running an accounting department.
The transition also challenged an investing instinct. Investors can wait for the “fat pitches,” Greenberg explains, but rapidly scaling companies cannot wait for every decision to be perfect. Her operating lesson is more immediate: “Velocity matters too.”

What happens when a company has money—but its CFO cannot reach it?
Over one extraordinary weekend, finance leaders found themselves confronting a threat few had anticipated: cash locked inside a failing bank, payroll approaching, and no certainty about what Monday would bring.
This episode brings together the experiences of Ben Gammell, Larry Roseman, Dan Murphy, Stacy Tumarkin, and Sarah Spoja. Their stories capture the crisis from different vantage points—from companies scrambling to protect their own liquidity to finance teams helping customers regain access to theirs.
The discussion is less about the collapse of a particular bank than about how CFOs respond when ordinary financial controls suddenly prove insufficient. It explores the decisions made under pressure, the communication required to steady employees and leadership teams, and the treasury practices reconsidered afterward.
The larger lesson is one CFOs understand well: resilience isn’t built during a crisis. It is built long before the crisis begins.