CFO THOUGHT LEADER

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.

How consumption models, AI, and rising complexity are reshaping the CFO mandateRevenue 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.“You can’t have probably right revenue.” — Sam ChungKey TakeawaysConsumption 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.Explore the Salesforce CFO ResearchThe conversation draws on Salesforce research examining the growing complexity of revenue models, the expanding mandate of finance leaders, and the adoption of AI and agents across the enterprise.Among the findings discussed: 65% of finance leaders report managing more than one revenue model, 71% say their companies are selling through more channels than a year ago, and 87% expect to add more consumption-based products.Explore the Salesforce CFO report at Salesforce.com/CFO-report.

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 StillwellAI 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.

For years, Middleby executives arriving at investor conferences faced a storytelling problem: 30 minutes wasn’t much time to explain three different businesses, each with its own brands, markets, investments, and stage of development.Today, CFO Brittany Cerwin has a different story to tell.Over the past 18 months, Middleby separated its food-processing business into a standalone public company and sold 51% of its residential kitchen business to private equity firm 26North. What remains is a more commercially focused Middleby—and, Cerwin says, a clearer capital allocation story. The change arrives after Cerwin spent 15 years inside the company, moving from financial analyst through controllership and chief accounting responsibilities while Middleby continued acquiring businesses and building its platform. Early on, she deliberately sought work that would keep her from being siloed. That breadth now meets a narrower portfolio.Middleby’s first capital priority, Cerwin explains, is investing in core operations, followed by returning value to shareholders, with acquisitions occupying a more opportunistic third position. Meanwhile, operational excellence—lean manufacturing, SKU rationalization, product teardowns, and margin improvement—has moved squarely onto the agenda.Perhaps the bigger shift is one of visibility. Middleby wants closer connections to customers, equipment, and service networks while expanding IoT capabilities and using AI to support both customer-facing platforms and internal finance work.