1135: Where Strategy Meets Finance in the Ad-Tech Revolution | Clayton Kossl, CFO, Basis Technologies

On his first day in investment banking, Clayton Kossl was “thrown right into the cauldron.” With few senior professionals in the small aerospace and defense group, junior bankers like him were expected to face company owners directly. “You had to understand the businesses inside and out,” he tells us. The experience forced him to blend analytical depth with the interpersonal agility needed to earn trust in every room.That mix of skills—numbers and nuance—became a through line in Kossl’s career. At ZocDoc, he joined a Strategic Finance team that partnered closely with the CEO and CFO, taking ownership of decisions that rippled across the fast-growing health-tech firm. The role taught him that financial modeling and relationship-building could coexist—and that influence often came from understanding how leaders think, not just how spreadsheets add up.Later, when Kossl joined Paintzen as one of roughly a dozen employees, those lessons proved vital. He rebuilt systems from scratch, partnered daily with the CEO and COO, and touched nearly every function of the business. “Someone had to do it,” he recalls. His ability to translate operational chaos into financial clarity helped guide Paintzen through its expansion and eventual sale to PPG Industries.Across these chapters, Kossl’s story reveals a consistent pattern: using strategy to tell better stories. Whether advising founders or steering finance in ad-tech today, he views storytelling not as spin, but as structure—the way finance can make complexity understandable and transformation achievable.

“InvoiceCloud is not just payments,” Chris Sands tells us. Sitting inside the company’s finance organization, he sees a platform built to change habits—helping businesses shift customers from paper invoices and mailed checks to fully digital transactions. The success metric, he adds, is simple: “Do more of their customers stop receiving paper invoices, stop mailing in checks, and do both of those things digitally?”That clear yardstick reflects how Sands thinks about growth. He describes a foundation rooted in existing customers even as the broader economy accelerates toward digital payment adoption. Utilities and insurers remain core markets, yet new verticals, such as consumer finance, beckon. Each expansion, he notes, must rest on data that confirms user behavior is truly changing.Inside finance, Sands has built what he calls a Strategic Finance function to mirror that discipline. The group handles special projects and, increasingly, AI initiatives—efforts he says once fell entirely within FP&A. Now they stand on their own “leg of the stool,” amplifying how finance supports innovation.That mindset extends beyond the department. Sands helped stand up an AI Ops team—an internal SWAT group that guides employees exploring AI tools. Instead of experimenting in isolation, staff can bring use cases to the team for help. For Sands, finance’s role is to stay analytical amid the excitement: “We can add more value … by helping the rest of the org with [AI] and using our finance skill set to understand where the best opportunities to create business value exist.”

In this episode of Planning Aces, host Jack Sweeney and resident thought leader Brett Knowles explore how finance leaders are approaching AI’s early returns—balancing efficiency, experimentation, and human judgment. CFO Craig Foster of Pax8 discusses how AI enablement is driving measurable productivity gains. CFO David Obstler of Datadog reflects on finding ROI amid rapid innovation and market demand. And CFO Ben Gammell of Brex shares why forecasting still requires human intuition despite data-driven progress. Together, their insights reveal a spectrum of FP&A strategies defining the modern CFO’s mindset toward AI adoption and business transformation.Brett Knowles’ Key TakeawaysBrett Knowles observes that finance leaders are positioning themselves along a broad continuum—from bold experimentation to cautious skepticism—when it comes to AI in planning. He notes a shift in tone: CFOs are now openly discussing productivity gains and cost efficiency rather than avoiding them. Knowles cautions against overreliance on ROI metrics, emphasizing instead disciplined cost management, pragmatic experimentation, and the evolving role of finance in navigating technology-driven transformation.

When Kimberlee Duval arrived at Cymbiotika, the wellness company was preparing a leap few bootstrapped brands attempt—moving from direct-to-consumer to retail shelves. “Our two owners, Charlene and Shahab, have done everything direct,” she tells us. “They wanted to build an organization for the long term.” That resolve led the company to take on debt rather than private-equity money to fund its Sprouts launch in 2024. The risk paid off: Sprouts highlighted Cymbiotika’s success in its quarterly earnings release, proof that intentional growth can outperform speed.Now, with products heading to 1,988 Target stores, Duval’s finance team is focused on scaling without losing clarity. “We restructured the finance function to align with that growth strategy,” she tells us, pointing to centralized operations in NetSuite, expanded FP&A and cost accounting capabilities, and the creation of clear SOPs. Technology, she believes, is the enabler that keeps teams lean and insights sharp.“There’s no reason to segregate between the groups,” she explains, describing her cross-channel approach to e-commerce and retail finance. AI tools and automated workflows now handle much of the transactional load, freeing her people to focus on analysis and collaboration.At the heart of her leadership philosophy is unity. “We’re a team … with a common purpose and a common goal,” Duval tells us. That ethos—pairing disciplined systems with shared intent—continues to shape Cymbiotika’s transformation from a digital wellness brand into a multichannel movement for intentional living.

When Steve Sutter joined Celigo five years ago, he stepped into a company positioned not as another SaaS app but as what he calls “the infrastructure, the piping, the plumbing” of business automation. Celigo, he tells us, moves data between systems like Salesforce, NetSuite, and Snowflake so companies can “create very sophisticated business processes” without the friction of disconnected silos.For Sutter, the real work of finance begins behind that plumbing. “As CFO, you have to build a sustainable business model,” he tells us, one rooted in clear unit economics—how each dollar of new recurring revenue is earned and what it costs to deliver value. That analytical discipline, he explains, gives finance a vantage point “no one else has,” allowing it to balance engineering ambition with go-to-market execution.Working inside a privately held, fast-growth environment, Sutter views resource allocation as both art and accountability. Sometimes, he says, companies must “invest in sales and marketing at an excessive rate” to gain traction—but the test is whether the model still makes mathematical sense. He partners closely with the CRO and CMO to watch metrics like the quota-to-OTE ratio and pipeline efficiency, adjusting as conditions change.Even at scale, Sutter keeps a simple mantra: acknowledge failure quickly. “As soon as you’ve acknowledged failure,” he tells us, “you can move on to something that will likely be successful.” It’s a principle that keeps Celigo’s growth disciplined—and its automation ambitions grounded in financial logic.

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.”