When Tom Steer joined Sokin as CFO, he already knew the international payments company unusually well. As an investment banker at FT Partners, he had advised Sokin through a capital raise during a difficult period for fintech funding. He knew its leadership, its financial projections, and the ambitions behind its growth.

What he had yet to experience was the challenge of building a finance organization capable of keeping pace.

Sokin helps multinational businesses manage cross-border payments, currencies, and treasury operations across fragmented banking systems. Its infrastructure supports payments to 170 countries, while a growing embedded-finance offering allows other companies to bring Sokin’s capabilities to their own customers.

For Steer, the challenge is deciding where to place the next investment. North America has emerged as Sokin’s fastest-growing market, while embedded payments and AI-enabled treasury tools present additional opportunities. Each requires capital, talent, and organizational attention.

The assumptions behind those decisions can change quickly. An anticipated shortage of engineers, for example, became less pressing as AI improved productivity, shifting attention toward sales and partnerships.

Inside finance, Steer encountered a different constraint: a lean team trying to accomplish too much. Three months into the role, he and his finance director stepped away from their daily responsibilities to map the work ahead.

“We can’t get this done on our own,” he recalls.

Today, Steer is building systems and teams designed for substantially greater transaction volumes. His guiding question is less about what finance can accomplish today than whether its infrastructure will still work when the business doubles in size.

At Vensure Employer Solutions, completing an acquisition is only the beginning. The company has acquired roughly 120 businesses in eight years, and each new addition enters an integration process containing some 1,400 steps. For CFO and President Kara Childress, the challenge is not simply bringing more companies into the fold. It is making certain the organization can absorb them without multiplying its own inefficiencies.

That challenge has become familiar territory for Childress, whose career took an unusual turn when she left public accounting to join Vensure as COO. Having previously served as the company’s outside auditor, she knew its finances. Operations offered something different: an opportunity to remove roadblocks and help people perform better.

As Vensure expanded into global payroll, HR technology, and human capital management services, Childress’s responsibilities broadened to include finance and the presidency. Along the way, she confronted a finance organization whose regional and divisional structure was duplicating work.

The acquisition engine was not slowing down. The finance organization needed to change before further growth made its existing structure untenable.

“We need to think about this differently,” Childress recalls.

The resulting reorganization reduced duplication and positioned finance to support additional acquisitions without continually adding staff. Meanwhile, a dedicated integration accounting team now brings acquired businesses into a common reporting framework beginning in their first month.

Today, Vensure is also expanding its AI capabilities while Childress concentrates on client retention, organic growth, and sales investment.

For a company accustomed to acquiring businesses, the next test is making its growing organization work better.

When Perry Beberman arrived at what is now Bread Financial, the company had a balance sheet problem. It was carrying too much leverage, had insufficient capital, and needed a more disciplined approach to funding its lending business. For a finance executive who had spent decades navigating consumer credit cycles, the assignment was familiar territory. The scale of the transformation, however, would demand patience.

Today, Beberman points to a substantially different financial foundation. Bread has paid down more than 70% of its parent-company debt, built capital beyond established targets, and shifted direct-to-consumer deposits from less than 5% of funding in 2020 to more than half.

The changes have given Bread greater capacity to invest in technology, support growth, and return capital to shareholders.

Still, Beberman is quick to explain that financial discipline is not simply about strengthening a balance sheet. At Bread, whose products include co-branded credit cards, private-label cards, and installment lending, the daily challenge is balancing the ambitions of retail partners with the economics of consumer credit.

Retailers want more approvals. Credit executives must manage losses. Finance must determine where the returns justify the risk.

“They collide all the time,” Beberman says of those competing priorities.

For him, such disagreements are not organizational failures. They are essential to making better decisions.

That philosophy also shapes Bread’s adoption of AI, its continuing finance transformation, and its approach to capital allocation. Technology may accelerate analysis and automate routine work, but Beberman sees little reason to surrender judgment.

After nearly four decades in finance, his operating principle remains remarkably consistent: growth matters, but only when the economics support it.

In 2023, Hippo faced what CFO Guy Zeltser describes as perhaps the worst quarter in the insurance company’s history. The response was not to chase growth harder. Instead, leadership made a decision that would have seemed counterintuitive during the company’s earlier expansion: shrink part of the business.

Between 2023 and 2024, homeowners insurance premiums declined approximately 30% as Hippo recalibrated the risks it was willing to carry. For Zeltser, the decision marked a turning point in a broader transformation—one that would move the company toward profitability and a more diversified business model.

Today, Hippo supports more than 60 insurance programs, generating fees and commissions alongside underwriting and investment income. That mix matters. Fee revenue offers greater predictability, while improved underwriting performance gives the company confidence to retain additional insurance risk.

Zeltser’s approach reflects an unusual career path. Before McKinsey and corporate finance, he worked in his family’s toy business, where customer complaints and everyday transactions made the consequences of business decisions tangible.

At McKinsey, another lesson emerged: even a board-approved strategy could stall when short-term financial targets overwhelmed longer-term investment.

Both experiences inform his current agenda.

Hippo is also deploying AI across claims and finance operations. Zeltser reports that AI now handles more than 80% of initial loss notifications, while finance has shortened its quarterly reporting timeline.

With Hippo targeting a threefold or fourfold increase in profitability between 2026 and 2028, Zeltser faces a familiar tension: delivering quarterly results without sacrificing the investments required to build a larger business.

Revenue models are becoming more complex—and for finance leaders, the consequences extend well beyond how a company bills its customers. As businesses combine subscriptions, consumption-based pricing, and other models, CFOs face new questions around predictability, visibility, cash flow, and the infrastructure needed to manage revenue from beginning to end.

Salesforce Chief Customer Officer Sam Chung brings an unusually broad perspective to these challenges. Over more than two decades at Salesforce, his roles have spanned revenue operations, finance and strategy, CFO of Salesforce.org, enterprise transformation, and customer leadership. In this conversation, Chung explores why CFOs must move further into operations, product, and technology; how AI and agents are changing the economics of finance; and why greater automation does not diminish the need for financial controls, precision, and human accountability.

• Consumption changes the finance equation. Usage-based revenue can strengthen the connection between what customers pay and the value they receive—but it also reduces predictability. Finance needs greater visibility into usage, billing, collections, and ultimately cash flow.
• The CFO is moving upstream. Today’s finance leaders cannot simply report the financial consequences of decisions made elsewhere. Increasingly, they need to participate in product, pricing, innovation, and operating conversations as those decisions are being made.
• AI needs an economic baseline. Rather than beginning with sweeping transformation, Chung advocates starting with use cases where companies already understand their operating metrics. Establishing a baseline makes it possible to determine whether AI is actually improving productivity, quality, and ROI.
• “Probably right” isn’t good enough for revenue. AI models can be probabilistic, while critical finance processes demand precision. The challenge is determining where AI can create value while maintaining the controls and deterministic outcomes that finance requires.
• Agents don’t transfer accountability. AI agents may increasingly perform work once handled by people, but responsibility remains with finance leadership. Controls, visibility, and oversight must evolve to encompass work performed by humans and agents alike.

When Tami Wilson-Ciranna joined Curative in April 2020, the assignment came with what now looks like a spectacularly optimistic assumption: three months.

“I met with Fred on a Tuesday and I started on Thursday,” she recalls. Curative was helping respond to COVID-19, and Wilson-Ciranna—who had retired and become bored—figured she would help with the pandemic. Three months became three years. Curative ultimately administered 36 million COVID tests.

Then came the harder question: What was phase two?

Curative wanted to remain in health care, but its leaders concluded that influencing care meant becoming the payer. The result was an employer health plan built around zero deductibles and zero copays, with members encouraged to complete an early baseline visit and engage in preventive care. Curative rolled roughly $500 million into starting the insurance business.

For Wilson-Ciranna, now president and CFO, the experiment is increasingly about what the data says. Medical loss ratios, provider costs, network economics, member behavior and wellness programs all come under scrutiny. Assumptions are expendable: Curative originally thought one health plan would suffice; market feedback convinced it to offer three.credentialing that Wilson-Ciranna says went from six months to 24–48 hours.

Perhaps that helps explain her operating philosophy: build, measure, fix—and keep moving. For the coming year, that means supporting Curative’s capital needs, expanding its provider network, entering additional states and adding members.

When Pegasystems began building its cloud business, the economics were hardly what investors would expect from a mature software company. Cloud gross margin was below 30%, recalls CFO and COO Ken Stillwell. The destination was roughly 80%. Getting there, however, required accepting that the path would not be straight.

At one point, Pega deliberately stepped backward on margin to make investments needed to scale the operation. “It put us probably off our margin targets by a year or two,” Stillwell says. “But it was a necessary investment for us to continue to scale.” Today, he says, cloud gross margin is approximately 80%.

That willingness to examine economics without losing sight of the customer runs through Stillwell’s thinking about Pega today. Growth comes largely from expanding existing customer relationships, making adoption—and the transaction volumes that follow—an important early signal. Stillwell looks for patterns across verticals, regions and customer cohorts to understand where expansion is taking hold. 1218 Ken Stillwell

AI introduces another economic puzzle. Pega chose not to build its model around maximizing token consumption. Stillwell argues that customers should use AI where it actually fits the work, selecting the appropriate model—or no AI at all—rather than treating consumption as the objective.

It is an approach consistent with the Rule of 40 discipline Stillwell helped spread throughout Pega: growth matters, but so do the economics behind it.

For the coming year, his priority is less about predicting every turn than preparing Pega to absorb them: staying agile, managing change and, as Stillwell puts it, remaining “calm and process focused” when the seas get rough.

CFO careers are often described through titles, companies, and accomplishments. But another force can quietly shape the journey: place.

In this themed episode of CFO Thought Leader, five finance leaders reveal how geography influenced the opportunities they encountered, the relationships they built, and the choices they made.

Mike Brower explains how Wyoming’s close-knit business community allowed relationships to carry him across industries and into new finance roles. Boston Red Sox CFO Tim Zue recalls an unconventional path through MIT, Bain, and the Boston public schools before an email to the Red Sox opened an unexpected door at Fenway Park. Gregg Clevenger describes leaving the demands of international investment banking for Rochester, New York—a move that became both a career and personal reset. Dallas Clement reflects on arriving in Atlanta for what might have been another career stop, only to repeatedly choose to stay with Cox Enterprises as other possibilities emerged. And Michael Bannon recounts expecting his move into an operating role to happen in the Bay Area before an opportunity in London redirected both his career and his family.

Together, their stories suggest that geography is more than background. Sometimes where a career unfolds helps determine what that career becomes.