In 2008, Beth Gaspich stood on the floor of the New York Stock Exchange, ringing the bell as RiskMetrics went public. What made the moment extraordinary was its timing—amid one of the most volatile markets in decades. The IPO decision, she tells us, came “down to the wire.” After months of preparing the S-1, long roadshows, and weekend work with auditors, leadership had to choose: delay indefinitely or seize a fleeting opening. They chose action, and the listing became a defining milestone in her career.

That experience shaped her conviction that preparation and clear communication are indispensable when markets are uncertain. It also foreshadowed the way she would later lead NICE through its own transformation. When she became CFO in 2016, NICE was largely an on-premise software company with roughly $1 billion in revenue. Today, she tells us, the firm is approaching $3 billion, with $2.2 billion in cloud revenue. “We don’t put boxes around people,” she notes, describing a culture where finance leaders are expected to help drive strategy, not just report results.

Her approach to AI investment echoes that belief. She explains that NICE’s AI and self-service ARR reached $238 million, growing 42% year-over-year. Rather than measure ROI only through headcount reduction, she emphasizes redeploying people to more strategic work. Internally, AI “champions” in each function track outcomes with KPIs. From ringing the NYSE bell to scaling a global AI platform, Gaspich’s journey illustrates how finance leaders can balance precision with boldness when transformation is on the line.

When David Obstler joined Datadog in 2018, the company’s co-founders had already built momentum with a product that observed modern cloud workloads. What struck Obstler was the alignment with a powerful long-term trend—the shift from legacy, on-premise systems to modern cloud applications. “It was a product that had a lot of product market fit in a really strong growing market,” he tells us.

From that foundation, Datadog scaled rapidly. Today, the platform serves more than 3,100 customers worldwide, including Samsung, Nasdaq, Shell, Autodesk, and Toyota. The company recently entered the S&P 500 after reporting more than $820 million in second-quarter revenue—a 28% year-over-year increase—alongside $200 million in free cash flow, Obstler tells us.

The CFO attributes the growth to Datadog’s unwavering commitment to product-led innovation. The company began in infrastructure monitoring and quickly expanded into logs, application monitoring, and security. “The company invests R&D at very high and consistent levels to continue to maintain and grow the platform,” Obstler tells us.

His own role centers on scaling the infrastructure needed to support expansion. That includes building global go-to-market operations and strengthening his team across financial planning, predictability, and business operations. “We’ve been investing behind this growth opportunity and doing it in a strong, prioritized way,” he tells us.

With new investments in AI, Datadog is preparing for its next chapter. For Obstler, disciplined prioritization and product-driven growth remain at the heart of how finance can fuel scale.

On her first day as CFO of UHY, Laura LaPeer asked a simple question: “Do you guys do Copilot?” She had grown accustomed to using Microsoft’s AI assistant for tasks ranging from summarizing documents to creating slides, and she wanted it in place immediately. The request, she tells us, reflected both her pragmatism and her view that technology should be leveraged quickly, but carefully, to support higher-value work.

That same instinct—to look beyond the surface of a task—has shaped her career. At an earlier company, LaPeer noticed that procurement and treasury were being handled transactionally. Purchase orders were checked for compliance, and cash was managed cyclically. By zooming out, she recognized the chance to turn these into strategic functions: evaluating vendor risks, aligning relationships with business goals, and putting idle cash to work. This shift, she tells us, allowed finance to deliver tangible impact.

Her time at ProQuest, where she witnessed growth through M&A, gave her a business lens she later carried into her CFO role at Plante Moran. Now at UHY, she applies the same perspective. With Summit Partners as a new investor, the firm is targeting $1 billion in revenue within five years, LaPeer tells us. Growth will come through both acquisitions and services such as outsourced accounting, valuation, and state and local tax.

To get there, she emphasizes unity. “One UHY,” she says, requires integrating regional groups, building the bench, and ensuring technology like Workday delivers consistent, firm-wide insights.

In 2018, Brex made a defining decision: rather than rely on middleware providers like Stripe or Marqeta, it built its own payments infrastructure from the ground up. That move, Ben Gammell tells us, gave the company a direct integration with MasterCard and the ability to issue corporate cards in “over 50 plus local currencies.” The choice, he explains, was born of necessity at the time but has since become a structural advantage, offering customers greater control and global reach.

That same principle of intentional investment extends to Brex’s software strategy. The company designs its expense management platform to meet the demands of sophisticated, high-growth businesses such as Arm and Anthropic. The result, Gammell tells us, is a solution that not only competes with legacy providers like Concur but also improves accessibility for smaller firms “with aspirations of being the next DoorDash or Coinbase.”

Partnerships further expand the ecosystem. Because Brex controls its processing stack internally, it can integrate with best-of-breed solutions—Navan in travel, Zip and Coupa in procurement—delivering the breadth that global enterprises require while keeping Brex at the center of the transaction.

Looking outward, the company recently began expanding into Europe. Gammell tells us the first priority is to better serve U.S. multinationals with operations abroad. Only later will Brex pursue wholly foreign clients. Still, he emphasizes discipline: the U.S. remains “the largest market by a country mile,” and maintaining focus there is key to balancing growth ambitions with profitability and investor confidence.

When Damon Lee reflects on his first conversations with C.H. Robinson’s CEO, he recalls how natural the alignment felt. “We spoke the same language. We were finishing each other’s sentences,” Lee tells us. For a finance leader whose ambition had long been to step into the CFO chair, the clarity of vision he encountered at Robinson made the opportunity stand out.

Lee emphasizes that Robinson’s longevity mattered. “A company that survived and thrived for 120 years—that’s special in its own right,” he tells us. The business, rooted in logistics services, relies on people as its core differentiator. “Our people really make the difference with our customers,” he adds, underscoring why the culture resonated with him.

What sealed the decision, however, was the simplicity of the CEO’s plan. “We’re going to outgrow the market, we’re going to expand our operating margins, we’re going to do both,” Lee recounts. Complexity, in his view, often derails execution. A straightforward mandate with conviction behind it gave him confidence that transformation was possible.

The CEO, Lee notes, wanted more than a traditional finance executive. He wanted someone who could “show up like a CEO,” bring lean discipline, and act as a true partner in reshaping the company. For Lee, this aligned perfectly with the operational mindset that had guided his career.

After more than a year in the role, he reflects simply: “We’re winning in the marketplace. We’re winning in the eyes of investors. So certainly it was the right move for me, no doubt.”

When Holly Grey first examined Horizon3.ai, she saw more than a cybersecurity startup. She saw a technology that could change the way companies safeguard themselves. Traditional pen tests, she tells us, are human-driven, vary widely by auditor, and usually happen just once a year. Horizon3.ai, by contrast, “started out as a technology alternative to pen testing.” Its platform can be deployed “within minutes, not hours or weeks or months,” Grey tells us, and has already executed “over 100,000 pen tests.”

The system identifies exposures, connects them to known threat actors, and—most critically—prioritizes which vulnerabilities to fix. It integrates directly with tools like Jira, creates tickets, and confirms results after remediation. “Even as a CFO, I want to know we’re not exposed,” Grey explains. That value proposition has already attracted more than 4,000 customers, she tells us.

Her decision to join Horizon3.ai was equally deliberate. Grey noticed two respected colleagues had recently come aboard, including the CRO. That relationship, she says, is vital: “I need to know that I can trust that CRO implicitly.” After doing her own diligence, Grey was convinced of the company’s momentum: “It’s hard to grow over 100% year over year, and do that multiple years, without having product market fit.”

The timing was fortuitous. Just as the company raised $100 million in Series D funding, its VP of Finance resigned. Horizon3.ai was ready to appoint its first CFO. “Here I am,” Grey tells us, “and I could not be happier in terms of joining.”

At 30, Jay Peir stepped into the CFO role at SunPower, a high-efficiency solar cell manufacturer. The appointment came after leading M&A and venture investments at Cypress Semiconductor, where SunPower was the largest portfolio company. “I had my first CFO experience at the age of 30,” Peir tells us, recalling how corporate development responsibilities opened the door to finance leadership.

That early leap reflected a broader pattern in his career: moving fluidly between finance and strategy. With dual engineering degrees from Stanford, Peir began in economic consulting before earning his MBA amid the rise and fall of the dot-com era. His background in technology and data analysis, he tells us, formed “my first chapter” and prepared him for navigating growth in fast-moving sectors.

A decade at Tableau deepened those lessons. When revenue slowed and the company’s stock “dropped about 50% in one day,” Peir was tasked with helping lead a shift to subscription. He emphasizes that success required aligning stakeholders across sales, marketing, and finance, ensuring teams could both understand and articulate changes to customers. “There’s both internal and external change management,” he tells us, noting the importance of investor communication as well.

Today, as Head of Strategy at Pigment, CFO Peir applies these experiences to scaling an AI-native planning platform. Pigment’s tools unify financial and operational planning, enabling companies to act on data with speed and flexibility. The company’s AI roadmap includes predictive analytics and autonomous agents, helping finance teams drive variance analysis, expense tracking, and forecasting more efficiently, Peir tells us.

When Craig Foster talks about artificial intelligence, he begins with scale. Pax8, the enterprise marketplace where he serves as CFO, connects vendors like Microsoft and CrowdStrike with 43,000 managed service providers. Those MSPs, he tells us, serve between 700,000 and 800,000 small and midsize businesses worldwide.

Against that backdrop, Foster describes how AI is reshaping both internal operations and external opportunities. Inside Pax8, teams are experimenting across functions—from customer support to accounting—to automate what was once manual. The company, he tells us, has set a target “to do 20% more with 20% less,” relying on AI tools that are already available. Efficiency gains are not hypothetical; they are part of the current planning cycle.

Externally, Foster sees what he calls “agentic marketplaces” emerging—ecosystems where AI modules act as labor components. Vendors are already building such agents, and Pax8 is designing its own. “We’re a marketplace,” he tells us, “so we need to incorporate those different… AI components and enable our downstream clients for efficiency.” He believes this wave, unlike earlier technology cycles, is reaching SMBs with unusual speed.

The finance leader is also watching economics evolve in real time. Data aggregated across Pax8’s network shows strong interest, but pricing remains unsettled. Foster compares today’s uncertainty to the early days of API marketplaces, when usage-based models became standard. The question now, he tells us, is how to split value between provider and customer—whether by consumption, per interaction, or shared outcomes. “That’s probably the biggest challenge in industry right now,” Foster says.