CFO THOUGHT LEADER

Sam Monti was working in finance at Rockwell Automation when a conversation about charging customers for technical support took an unexpected turn. A salesman suggested collecting a fee for access to the company’s engineers. Monti had another idea: Why not make it a membership, like a country club?

The resulting subscription business generated $150 million in revenue in less than three years. For Monti, it was an early lesson in how rethinking a company’s operations could fundamentally change its economics.

More than two decades later, that experience has particular relevance at SolarWinds, where Monti is C...

At Greyson Clothiers, opening a new store can mean committing capital long before the first meaningful returns arrive. For CFO Neely Rosen, that gap between investment and payoff has become one of the defining challenges of helping a growing apparel company scale.

Greyson's business began in wholesale before expanding into e-commerce and company-owned retail stores. Its Detroit flagship, Rosen notes, has become one of its strongest performers. Now, following a capital raise in late 2024 and a NetSuite implementation, the company is preparing to introduce its own footwear line while expanding its retail presence.

The question...

For Anaplan CFO Hemant Kapadia, one of the more revealing measures of the company’s transformation isn’t revenue growth alone. It’s the fact that Anaplan has nearly the same number of employees it had when it was taken private in 2022—even as annual recurring revenue has grown from approximately $600 million toward $1.4 billion.

The company has also become materially more profitable, generating free cash flow margins in the mid-30s. That financial flexibility has helped fund a $500 million investment commitment spanning infrastructure, platform development, new applications, and artificial intelligence.

Yet Kapadia’s ambitions extend beyond Ana...

At SuiteWorld 2026, NetSuite’s founder outlines how AI is transforming business software—and what the shift means for CFOs.

When Evan Goldberg, founder and executive vice president of Oracle NetSuite, declares that ERP as we know it is over, the statement carries particular weight. Goldberg helped pioneer cloud-based enterprise software in 1998, challenging the conventional wisdom about how businesses should manage their financial and operational systems.

Nearly three decades later, he sees artificial intelligence driving an equally consequential transformation.

Speaking with CFO Thought Leader at SuiteWorld 2026 in Las Vegas, Goldberg described a future in whic...

When Steve Fox joined Every Man Jack in 2021, the men’s personal care brand had a new private equity owner and an ambitious growth agenda. Carlyle Group saw an opportunity: a widely distributed brand that had never invested heavily in marketing. The challenge was finding the operating leverage to fund that investment.

For Fox, the answer increasingly lies in technology.

At Every Man Jack, a company known for its outdoor-inspired grooming products, the finance team has remained at five employees even as transaction volume has tripled. Fox credits investments in technology and a growing emphasis on...

When Joe Iantosca arrived at Cyera as CFO, his first hire wasn't an accountant or an FP&A professional. It was a data engineer.

For Iantosca, the decision reflected a conviction formed over years of working inside technology companies: Finance cannot help steer a business without reliable access to the information driving it.

That conviction first took shape at Palantir, where he witnessed the impact of centralizing financial and operational data. At BetterCloud, where his responsibilities eventually expanded into the COO role, he carried the lesson further, connecting product, marketing, and business information into a...

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...

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 it...

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...

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 6...

How consumption models, AI, and rising complexity are reshaping the CFO mandate

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.or...

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. T...

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 appro...

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. brittany-david-jack

The change arrives after Cerwin spent 15 years insi...

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 un...

At Zapier, the rise of AI is changing more than the automation products customers build. It is reshaping how the company organizes, invests, prices its offerings, and thinks about its next stage of growth.

COO and CFO Ryan Roccon describes Zapier’s emerging role as the place where AI-built work actually runs. As tools such as Claude, Cursor, and ChatGPT make it increasingly easy to build applications and agents, he sees a different challenge emerging: keeping those automations reliable, observable, auditable, and cost effective once they enter production.

That challenge is influencing Zapier’s product and...

AI is rapidly changing not only what finance technology can do, but how CFOs should think about the technology stack itself.

In this bonus episode of CFO Thought Leader, David Den Boer, CEO of Column Five and Darwin Analytics, joins Jack Sweeney to explore how AI is reshaping enterprise performance management—and why finance leaders may need to rethink long-held assumptions about EPM platforms, data systems and analytics.

Den Boer describes a market in which capabilities once associated with EPM are increasingly emerging from multiple directions. Large language models, data platforms, business intelligence tools and EP...

At Aledade, CFO Jessica Somers is helping finance navigate a business where investment decisions can take years to fully reveal their value.

The technology-driven, physician-led company works with more than 3,000 primary care practices and touches more than 3.6 million patients, using data and technology to support proactive, preventive care. Its value-based model also creates an unusual finance challenge: connecting better patient outcomes with healthcare savings and, ultimately, financial performance.

That long-term orientation shapes how Somers approaches capital allocation. Aledade has built its own technology platform rather than relying on another company’s roadmap, reflecting what Somers de...

For Jack Gordon, the CFO role at Harri increasingly extends beyond finance—and into the mechanics of how an AI-powered business scales.

Harri, a workforce operating system focused on hospitality, has evolved from a point solution into a broader platform spanning talent acquisition, workforce management, and employee engagement. Gordon says the company’s opportunity rests partly on years of data accumulated across mission-critical workflows, an advantage that becomes increasingly important as AI reshapes workforce technology.

That evolution is also reshaping Gordon’s finance agenda. As Harri rolls out its AI platform, understanding the changing unit econom...

When Martin Uhrik compared the margins of two visual-effects brands at Technicolor, one appeared far more profitable than the other. Uhrik tells us the reported difference prompted him to investigate. One brand showed project results only to the direct-margin level, rather than revealing fully absorbed profitability.

Uhrik says he asked the business-unit CEO why the company was not showing creatives “the true state of the business.” The response was resistance: management feared that exposing weaker bottom-line results could cost the premium brand its talent and luster.

Uhrik insisted. According to him, the business began showing crea...

Shortly after Dan Barzily became CFO of Tipalti, a go-to-market transformation altered the company’s working-capital profile. One quarter later, Barzily tells us, the company missed its forecast across multiple parts of the P&L.

The surprise reached back to a subject he had barely considered since his university accounting class. “It really hit me,” Barzily recalls. “I’m now the CFO, and I’m in charge of those things.”

Until his appointment, Barzily says, he had never expected to become a CFO. He studied engineering, where he developed skills in analytics, accuracy, modeling, forecasting, and making ass...

Jonathan Ma recalls being at his parents’ home in Nebraska one Saturday when his Morgan Stanley boss called with advice: pursue an opportunity at Sutter Health. After nearly 15 years, the mentor believed the retiring treasurer’s position could be Ma’s next step.

Ma tells us he had not considered the opportunity. Although he knew Sutter Health’s mission and some of its people, he says the call “planted” the seed. His mentor had seen something in him that he had not yet recognized.

That moment echoed the way Ma describes his development at Morgan Stanley. He...

Six weeks before Lehman Brothers went under, Shiv Verma tells us, he joined a hedge fund as the world felt like it was falling apart. After building structured-credit and CLO models at J.P. Morgan from 2006 to 2008, Verma says he helped buy back assets originated at par for five cents on the dollar.

A mentor there supplied a rule Verma still carries: “The best trade you ever make is often the trade you don’t make.”

For Robinhood’s CFO, the line offers a double meaning—and a little fun. In the interview, however, Verma applies it...

Ross Grainger remembers an early chapter of his career when finance was only one part of the job.

After stepping outside a traditional finance path to own and operate a Mako auto-body franchise, Grainger tells us he learned what it meant to “act like an owner.” That sometimes meant cleaning toilets, learning to paint cars, welding, doing body work, handling customer service, and making outside sales calls. But the experience also taught him another lesson: even if a leader can do everything, “you shouldn’t do those things forever” if they pull you away from where you can provid...

Cal Brouilette recalls a sleepless night in Houston, speaking at 3 a.m. with someone from Blackstone about a purchase-and-sale agreement and transition-service agreements. It concerned a power-plant portfolio sale at Direct Energy, a Centrica subsidiary, that Brouilette places in 2013.

According to Brouilette, the assignment arrived in late September, when the CEO wanted the portfolio sold and announced before year-end. That left at most 120 days. Brouilette says he was managing finance and accounting, functioning as a business-unit CFO and loading up on MBA classes at Rice because his job had seemed stable.

The new assignment changed...

Jamie Schroeder’s finance career began on the shop floor at Ford Motor Company. As part of Ford’s rotational development program, Schroeder tells us, he spent a month working in the paint shop at an assembly plant outside Cleveland. The experience was designed around “learning the business and getting your hands on the business” so that finance could become an informed partner to operations.

That operating mindset followed Schroeder to Scotts Miracle-Gro, where unfamiliar assignments became a recurring source of development. According to Schroeder, he was repeatedly placed in situations involving ambiguity, collaboration, and the need to “crea...

At Timken, it was generally known that Phil Fracassa knew he would become CFO after the company separated its steel business. But first, he tells us, the board gave him a different assignment: lead the project management office and set both resulting companies up for success.

The separation followed pressure from an activist investor and extensive board consideration of strategy, stakeholder impact, operating performance, capital allocation, risk, and long-term shareholder value, according to Fracassa. Once the decision was made, his team had just under a year to carve out a business that had been part of Timken...

Matt Ostrower remembers losing sleep over a decision that carried consequences for employees, lenders, and shareholders.

At Site Centers, Ostrower tells us, the management team was confronting two challenges. Investor fears about the internet’s impact on retail real estate were depressing stock and bond valuations. Then Hurricane Maria struck Puerto Rico, leaving a portfolio of company assets out of commission for months.

The immediate pressure was to reopen properties and navigate the crisis. But Ostrower says the team forced itself to “pull back” and consider how the company could emerge positioned for growth.

Work...

Andrew Korn tracks growth first. EliseAI had surpassed $200 million in annual recurring revenue when he spoke with us, and Korn tells us the company had maintained year-over-year growth above 100% throughout his four and a half years there—“correlation, not causation,” he adds.

That growth gives finance a clear assignment. According to Korn, EliseAI monitors gross margins and burn while ensuring its spending remains prudent and directed toward investments capable of moving the business forward.

The company operates in housing and healthcare, two industries Korn describes as representing about 40% of U.S. GDP combined. He tells us bot...

In April 2020, Laura Miller stepped into her first CFO role at Pampered Chef. According to Miller, she was pregnant with her second child, working with a new CEO and joining an executive team that had never worked together in the building before the pandemic sent everyone home.

Demand was anything but predictable. Miller tells us that Pampered Chef’s independent consultants could hold parties online while consumers, confined to their homes, purchased kitchen equipment and looked for ways to earn money. That summer brought a business boom—and immediate pressure on working capital, supply chains and forecasting.

In the early months of Francisco Partners, Samantha Greenberg sat in a room on folding chairs with the firm’s cofounders and one other colleague, planning the business.

According to Greenberg, the private equity firm was pursuing an idea that many considered impossible in the late 1990s: executing leveraged buyouts of technology companies. Greenberg tells us she was drawn to the vision because it challenged the belief that technology businesses could not be predictable or capitalized with debt.

During the firm’s first year, Greenberg says, the team closed its first fund. She helped build oper...

What happens when a company has money—but its CFO cannot reach it?

Over one extraordinary weekend, finance leaders found themselves confronting a threat few had anticipated: cash locked inside a failing bank, payroll approaching, and no certainty about what Monday would bring.

This episode brings together the experiences of Ben Gammell, Larry Roseman, Dan Murphy, Stacy Tumarkin, and Sarah Spoja. Their stories capture the crisis from different vantage points—from companies scrambling to protect their own liquidity to finance teams helping customers regain access to theirs.

The discussion is less about the coll...

In high school, Gary Vecchiarelli received day-old copies of Investor’s Business Daily from a business teacher. Stock prices still appeared in fractions, and the teacher told him that he would know he had made it when he rang the bell on Wall Street.

Vecchiarelli tells us that the remark stayed with him for decades. He later rang the Nasdaq bell—an experience made more meaningful because his family knew the story. Long before that moment, however, he had begun ordering boxes of annual reports and reading financial statements he did not yet fully understand. He was draw...

What does it take for a CFO to restore credibility?

Every finance leader eventually encounters a defining moment when confidence has been shaken—whether by slowing growth, a financial crisis, or years of eroding investor trust. In those moments, success depends on more than financial expertise. It requires disciplined execution, transparent leadership, and the ability to deliver on commitments when every decision is under scrutiny.

In this special compilation episode of CFO Thought Leader, we revisit three conversations that reveal how credibility is earned—and, when necessary, rebuilt.

Aidan Viggiano, CFO of Twilio, refl...

Mark Khavkin often finds his best ideas somewhere near the Golden Gate Bridge.

The Rula CFO tells us that he bikes from San Francisco across the bridge and into Marin County—not to compete, but to clear his mind, enjoy the view, and stop for a latte in Sausalito. “A lot of times great ideas come somewhere just before or after the bridge,” Khavkin says.

That preference for space and perspective also appears in how he leads. Compared with a decade ago, Khavkin says that he has become more comfortable trusting people to reach the right...

John Kinzer still remembers sitting in a closed meeting at MCI, presenting revenue results, when something unexpected caught his attention. It wasn’t the numbers he was reporting—it was the questions coming from the FP&A team. Listening to their discussion, he realized, “I also want to see that side of it,” Kinzer tells us. That moment led him from revenue reporting into business planning, where a manager helped shape the analytical skills that would define his career.

Looking back, Kinzer tells us those early experiences proved invaluable. Long-distance telephone plans behaved much like today’s subscripti...

When Shane Hostetter arrived at Chemours in 2024, he stepped into a company facing liquidity challenges while also pursuing important long-term growth opportunities. His goal was not to replace decades of institutional knowledge but to complement it. Chemours CEO Denise brought nearly forty years of experience with DuPont and Chemours, while Hostetter brought an external perspective. Combining those viewpoints, he tells us, helped create “the best of both worlds.”

That approach reflects much of Hostetter’s broader leadership philosophy. Rather than viewing finance solely through the lens of reporting, he focuses on building a stronger foundation for future growth...

Three accomplished CFOs. Three candid conversations. One revealing look at how finance leaders think about acquisitions before the headlines ever appear.

In this special CFO Thought Leader edition, we revisit conversations with Jonathan Carr, former CFO of Armis, James Redfern, CFO of Reltio, and Toby Driver, CFO of IdeaGen. Each discusses acquisitions from a different vantage point—planning, integration, organizational readiness, and the people challenges that ultimately determine whether a transaction creates lasting value.

What makes these discussions especially compelling is their timing. Carr and Redfern shared their perspectives months before their companies were acquired. Se...

Sinohe Terrero still remembers the timing. He joined Envoy in January, only to see the workplace transformed just two months later as offices around the world shut down because of COVID. The company had been building products for offices, but suddenly, almost no one was going to the office, Terrero tells us.

That abrupt shift forced Envoy to rethink its future. The company quickly introduced a product called Protect to help organizations safely welcome employees and visitors back into their facilities. From there, it expanded into desk management, room scheduling, deliveries, analytics, and ultimately a broader suite...

Taking a Company Public: What CFOs Know

What does it really take to prepare a company for life as a public company?

In this special CFO Thought Leader compilation, we revisit three conversations with finance leaders who helped guide some of the technology industry's most recognizable companies through the IPO journey. Rather than focusing on the transaction itself, these CFOs share what happened behind the scenes—the operational changes, leadership decisions, and financial discipline required long before the opening bell rang.

John Kinzer, former CFO of HubSpot, explains how preparing for an IPO re...