CFO THOUGHT LEADER

In Episode 47 of Planning Aces, Jack Sweeney and resident thought leader Brett Knowles explore the evolving role of FP&A through the lens of three forward-looking CFOs. Dan Zhang (ClickUp), John Rettig (Bill), and Josh Schauer (insightsoftware) share how they’re driving enterprise agility, leveraging AI to eliminate inefficiencies, and rethinking capital allocation. From Zhang’s battle against “SaaS overload” to Rettig’s “prove-it mentality” and Schauer’s daily forecasting, each CFO reveals a distinct approach to enabling smarter, faster decision-making. Their insights offer a compelling look at how modern FP&A leaders are transforming strategy execution in real time.

Host Erik Zhou, CAO at Brex, sits down with Richie Mashiko, Fractional CFO, to unpack the financial complexities of running high-growth e-commerce and CPG brands. From measuring the right things to navigating ad spend, pricing strategies, and fragile supply chains amidst tariffs, Richie offers a unique operator’s perspective on what it takes to drive sustainable growth in today’s market.

Andrew Casey remembers a moment when colleagues truly looked to finance for leadership. At ServiceNow, a then‑$400 million company with little go‑to‑market infrastructure, the team faced a long list of missing elements: no functioning comp plan, no partner ecosystem, and no clear strategy for scaling sales. “Whenever people said they didn’t know how,” Casey recalls, “I started raising my hand and said, I don’t know either, but I know what we’re going to go do… and then we’re going to adjust as we go.” That willingness to lead through uncertainty became a turning point in his career.ServiceNow would grow from $400 million to $4.5 billion during his tenure, and colleagues still use the pricing and deal frameworks he created, he tells us. The experience cemented his approach: chase experiences, not titles, and transform finance into a partner that drives business outcomes.That mindset carried into his first CFO role at WalkMe in 2020, where, just two weeks in, COVID forced an immediate office shutdown. “We didn’t even have a work‑from‑home policy,” he tells us. The sudden disruption forced him to navigate crisis management, team alignment, and IPO preparation simultaneously.His journey through Sun Microsystems, Symantec, Oracle, HP, ServiceNow, and Lacework sharpened his ability to guide transformation and scale. Today, as CFO of Amplitude, Casey draws on those lessons to help a smaller public company grow with discipline. Each chapter—from being involved in 37 acquisitions at Oracle to steering turnarounds—reflects a career built on stepping into complexity, listening first, and leading change with confidence.

When Konstantin Dzhengozov turned down a corporate development role in the U.S., he wasn’t walking away from opportunity—he was running toward a different kind of growth. Having helped lead the FP&A function at a fast-scaling Bulgarian tech firm through its acquisition by a U.S. public company, Dzhengozov knew what came next if he stayed the course. But “the unknown… just felt right,” he tells us. So he stayed close to Bulgaria’s booming startup scene—and co-founded Payhawk.In the early days of Payhawk, Dzhengozov was a one-man finance team, juggling everything from chart of accounts and payroll to fundraising and compliance. “You kind of become a bottleneck at some point,” he tells us. “The sooner you realize that, the better.” His approach: build ahead of need. His first finance hire brought Big Four audit expertise. Next came senior hires in FP&A and tax as the company expanded across Europe and the U.S.Rather than compete as another card issuer, Payhawk positioned itself as a software company from the start, charging a subscription to solve real pain points Dzhengozov had faced firsthand: poor data visibility, lack of control, and disjointed processes. The company’s dual-revenue model and international-first mindset helped it raise $240 million and become Bulgaria’s first unicorn, he tells us.Today, Dzhengozov envisions AI helping CFOs compress decision cycles and model complex scenarios instantly. Still, he remains grounded in principle: “Finance should be enabling the business to grow,” not just reporting on it.

Dan Zhang, CFO of ClickUp, oversees diverse operations with a focus on integrating AI into productivity. She discusses how ClickUp's platform consolidates tools like project management and communication, revolutionizing work for over 4 million teams globally. Zhang highlights the explosive growth of ClickUp's AI capabilities and emphasizes a mindset of continuous evolution, viewing each day as a new beginning. She also reflects on her unique journey from journalism to finance, showcasing the blend of creativity and strategic vision in her approach to leadership.

Tim Vipond, Co-founder and CEO of the Corporate Finance Institute, shares his journey from tackling complex financial models in mining to revolutionizing finance education online. He emphasizes the importance of real-world skills alongside theoretical knowledge. Discussing the integration of AI into courses, he highlights how CFI tailors certifications to current job markets, ensuring nearly 3 million students are workforce-ready. Vipond advocates for continuous learning, showcasing success stories that demonstrate the value of adapting finance teams to today’s rapid changes.

Lisa Cummins Dulchinos, CFO of Ayar Labs, shares her journey bridging deep tech and finance. She discusses how her team, filled with tech experts, simplifies complex innovations like TeraPHY, a chip that enhances data transfer with lasers. Dulchinos emphasizes the long-term cost savings despite higher upfront costs, making the tech relatable. From navigating emotional intelligence in leadership to the transformative power of storytelling, she highlights essential skills for finance leaders in a rapidly evolving landscape.

When Kevin Wall first stepped into industry from public accounting, it wasn’t by accident—it was through a client he already knew well. The company, in the midst of an ERP conversion and preparing to go public, saw in Wall someone who understood both their numbers and their needs. “They were familiar with me. I was familiar with them,” he tells us.That early pivot from audit into operational finance set the tone for a career defined by depth over speed. Wall spent 13 years at Alcatel-Lucent and a decade at FIS, climbing steadily while broadening his remit from general accounting to pricing, FP&A, and global finance operations. His longevity at these firms, he tells us, allowed him to “move and see new things under one roof” while growing his leadership footprint.Today, as CFO of Stax Payments, Wall is again stepping into transformation. The company, which serves over 40,000 SMBs and processes more than $20 billion in volume annually, is preparing to launch its own end-to-end processing engine. Wall’s priorities reflect a blend of commercial focus and operational precision: “It’s the top of the funnel,” he says, referencing lead generation, “and speed to revenue.”A self-described servant leader, Wall believes in “clearing obstacles” so teams can grow. That mindset also drove a past strategic move—reorganizing finance functions like billing and AP to other departments. It was a bold step, but one grounded in clarity: “Let’s really define what we want finance to be,” Wall tells us.

When Josh Schauer joined Longview, a Toronto-based software company, he had no idea that a transformative chapter of his career was just a few years away. In 2020, Longview was acquired by insightsoftware—a turning point that brought both uncertainty and opportunity. “It’s kind of equal parts fear and optimism,” he tells us. “You wonder: Am I going to have a job coming out of this?”But his then-CFO advocated for him, making clear to the acquiring company, “they can’t lose you.” That moment, Schauer tells us, “swung the pendulum to the opportunistic side.”Rather than move on, Schauer leaned in—ultimately rising to become CFO of insightsoftware five years later. Today, he leads finance for a company that has completed 31 acquisitions and delivers AI-powered tools for CFOs—tools Schauer uses himself.Early in his career, a mentor CFO gave Schauer full ownership of budgeting, board reporting, and strategic analysis. That experience shaped his belief that finance is “a strategic operating partner.” It’s a mindset that drives his approach today, from implementing daily agile forecasting to integrating AI across functions.“We are an AI-first organization,” he explains, with AI liaisons and company-wide training supporting adoption. Though measuring ROI can be tricky, he sees clear returns in efficiency and insight.Still, he keeps people at the center: “Is the team taken care of? Do they feel engaged?” For a CFO who’s navigated acquisitions and transformation, Schauer tells us, team satisfaction remains one of his top priorities.

When Nathan Winters led a supply chain team earlier in his career, he noticed something that would shape his leadership style: “The credibility you get by the operating leaders when they see you out in the field… is incredibly important.” Whether visiting customers, walking a manufacturing floor, or sitting in on operating meetings, Winters found that physical presence fostered trust—and that trust gave finance a real seat at the table.Today, as CFO of Zebra Technologies, Winters continues to emphasize business partnership grounded in proximity to operations. In the four years since he stepped into the CFO seat, Zebra has weathered post-COVID surges, global supply chain disruptions, and enterprise restructuring. The company’s product footprint—often “hidden in plain sight,” from grocery checkout scanners to hospital wristbands—has expanded to include robotics and machine vision, Winters tells us.He’s also broadened his own remit, taking on IT and cybersecurity leadership, including oversight of both the CIO and CISO. In that time, Zebra has reduced China-based production from 80% to 30% and introduced new AI capabilities like “Zebra Companion” to automate shelf management for retailers. Internally, Zebra launched a private LLM instance—“Z-GPT”—to streamline tasks from expense report queries to sales presentations.“Your job isn’t to just close the books,” Winters tells us. “If you’re not analyzing… finding new ways to think about things… you’re getting passed up.” At Zebra, finance is not just a control function—it’s a strategic force embedded in every operational stride.