CFO THOUGHT LEADER

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.

In high school, Gary Vecchiarelli received day-old copies of Investor’s Business Daily from a business teacher. Stock prices still appeared in fractions, and the teacher told him that he would know he had made it when he rang the bell on Wall Street.
Vecchiarelli tells us that the remark stayed with him for decades. He later rang the Nasdaq bell—an experience made more meaningful because his family knew the story. Long before that moment, however, he had begun ordering boxes of annual reports and reading financial statements he did not yet fully understand. He was drawn to CFOs who carried financial responsibility while dealing with Wall Street.
That early interest eventually became a career defined by complex businesses and difficult financing choices. At CleanSpark, Vecchiarelli recalls confronting one such decision during a Bitcoin bear market. Debt was prohibitively expensive, and an at-the-market equity program was effectively the company’s only source of growth capital.
According to Vecchiarelli, CleanSpark faced an opportunity that required issuing shares at approximately $2.50. The decision was painful, but the capital funded land and power that the company now expects to convert into billions of dollars of shareholder value.
The experience gave Vecchiarelli a lasting appreciation for “optionality.” He tells us that CleanSpark can now consider high-yield debt, convertible securities, equity, and borrowing against its Bitcoin holdings. That range matters because, as he puts it, markets can be “real fickle.”
For Vecchiarelli, strategic finance is not simply raising and spending money. It means connecting execution, valuation, and capital so that today’s difficult decision creates more choices tomorrow.

What does it take for a CFO to restore credibility?
Every finance leader eventually encounters a defining moment when confidence has been shaken—whether by slowing growth, a financial crisis, or years of eroding investor trust. In those moments, success depends on more than financial expertise. It requires disciplined execution, transparent leadership, and the ability to deliver on commitments when every decision is under scrutiny.
In this special compilation episode of CFO Thought Leader, we revisit three conversations that reveal how credibility is earned—and, when necessary, rebuilt.
Aidan Viggiano, CFO of Twilio, reflects on stepping into the role during a period of sweeping change. With growth slowing and difficult decisions ahead, she shares why rebuilding confidence began with one simple principle: do what you said you would do.
Eric Brown, now CFO and COO of Cohesity, takes us back to the near-existential crisis at MicroStrategy, where he and the leadership team were forced to stabilize the business, make painful decisions, and lead through extraordinary uncertainty. His story underscores the critical partnership between a CEO and CFO when an organization's future is on the line.
Finally, Paul Lundstrom, now CFO of Copeland, looks back on his tenure at Flex and earlier leadership at Aerojet Rocketdyne, explaining how stronger financial controls, operational discipline, and consistent execution can gradually restore investor confidence and reshape how the market values a company.
Together, these conversations form The Credibility Playbook—a practical look at how exceptional CFOs navigate some of the most challenging moments in corporate leadership and emerge with something every organization depends on: trust.

Mark Khavkin often finds his best ideas somewhere near the Golden Gate Bridge.
The Rula CFO tells us that he bikes from San Francisco across the bridge and into Marin County—not to compete, but to clear his mind, enjoy the view, and stop for a latte in Sausalito. “A lot of times great ideas come somewhere just before or after the bridge,” Khavkin says.
That preference for space and perspective also appears in how he leads. Compared with a decade ago, Khavkin says that he has become more comfortable trusting people to reach the right result, even when their path differs from the one he might have chosen. Rather than intervening with detailed instructions, he now tries to provide context. “I’m less prescriptive than I was ten years ago,” he tells us.
The shift does not mean avoiding hard decisions. At Rula, Khavkin says that new investments require clearly defined checkpoints and agreement—made in advance—about when the company will increase its commitment or stop an initiative. Once teams, careers, and expectations form around an experiment, he explains, ending it becomes difficult at a human level.
The same discipline shapes his view of AI. Khavkin cautions finance leaders against evaluating the technology primarily through cost savings. According to Khavkin, the greater opportunity is enabling people to perform higher-level work, make decisions faster, and access more organizational context.
For Khavkin, leadership is not about directing every turn. It is about creating the conditions for others to navigate—then knowing when to provide context, when to challenge assumptions, and when to let the road produce the answer.