CFO THOUGHT LEADER

We can’t help but cringe when a finance leader tells us that they don’t want to be known as “the CFO of ‘No’”—that shopworn characterization of CFOs who seem to enjoy giving thumbs down verdicts.   

So, we were pleased when CFO Jim Morgan of CallRail steered clear of the trite trope when he recently joined us as a return guest.

Nonetheless, we were still curious as to what has replaced the iconic “thumbs down” when it comes to finance leaders projecting their diligence onto the monitoring of risk and governance practices.

“I probably have it a little bit easier than most CFOs because one of our five culture statements is Mind the business—which is music to a CFO’s ears,” comments Morgan, who adds that the simple phrase is best voiced in a question.

“’Are we minding the business?’ is what I ask our team every day,” reports Morgan, as if prescribing for the CallRail corporate culture a regimen of essential vitamins and minerals.

Notes Morgan: “It’s naturally easy for me to be the culture carrier of this because I am able to leverage that business mentality as we focus on being a business partner to all of our different departments.”  

Also, the question’s emphasis on the “we” helps to amplify a business’s shared mission and achieve “buy in” when it comes to some prickly decisions.  

“It’s a nice sort of framework for using to sort of step back with folks and say, ‘Are we minding the business?’—as opposed to, say, just stating ‘I don’t think that’s a wise spend of dollars’ or ‘That doesn’t really follow our talent mandate,’” remarks Morgan, who again emphasizes that within CallRail, Mind the business is not just a popular phrase but also one that the company has codified.

Says Morgan: “Mind the business is how we ultimately achieve trade-offs and prioritizations across the business—it’s what we call a culture statement.” –Jack Sweeney 

When Ambereen Toubassy decided that it was time to start up her own hedge fund, it's likely that no one cast doubt on the experienced investor’s grand plan. That is, no one except Toubassy herself.  

After 7years as an investment banker with Goldman Sachs and a dozen running hedge funds, Toubassy says, she told herself, “Okay, this is a moment, I have a track record, I should start my own hedge fund.”

Thus with some freshly drafted marketing collateral in hand, she initiated the early round of discussions that would allow her to begin raising capital.  

“When I started doing this, I realized my that heart wasn’t in it—I told myself, ‘Okay, if your heart isn’t in this, you have no business asking other people to entrust you with their capital,’” recalls Toubassy, who notes that her outreach had put her in touch with a span of finance professionals from her Goldman Sachs years, including a number who had exited the investing world to take on a variety of operating roles—including CFO positions.

“What clicked for me and why I made the shift to operations was how much time CFOs spent in talking about the people with whom they were working,” reports Toubassy, who points out that while the guiding principle of her career had always been to “always be learning,” her discussions with CFOs made clear that there was more to learn.

Remarks Toubassy: “I'd always sort of had this inkling that when I was managing a portfolio and tickers, I didn't get as much of that people mentorship experience as I would have liked to have had.”

Today, after having served in multiple CFO roles, Toubassy keeps people top-of-mind when offering advice to new finance leaders.

For one thing, she advises, “Spend time gathering context and developing relationships with your peers and the business leaders for all of the other functions.”

Moreover, Toubassy exposes the people factor in CFO success from the perspective of output and input metrics.

“The financials are output metrics, and a CFO cannot influence them or change them because they're exactly that," remarks Toubassy. "To effect change, you need to understand and influence the inputs that go into the business.”

Perhaps not surprisingly, though, Toubassy quickly circles back to her relationship-building advice: “You need to spend time with the head of each of the business functions. You need to have a relationship with each of these people. You need to be able to sort of put yourself in their shoes and say, ‘How would that person effect change?’ And, over time, the output metrics that finance cares about will change.”

Meanwhile, Toubassy finds little or no irony in the title “chief finance officer.”

“We have this tendency to jump straight into the financials or outputs because that’s who we are," she says. "And, we are the chief financial officer.” –Jack Sweeney

When Darren Cooper was named CFO of Reveal Group of Melbourne, Australia, in 2019, there was no friendly board member or executive recruiter seeking kudos for having completed a successful a CFO search.

Instead, Cooper says, his twist of fate was due to a personal relationship that he had established with Reveal management after his prior company, Adcorp Holdings, had hired Reveal to provide it with services inside the intelligent automation realm.

Originally from South Africa, Cooper had been counted among the finance rank-and-file of a Johannesburg staffing company only 5 years earlier. Turn back the clock to those times, and you would find Cooper spearheading a number of the staffing company’s strategic IT projects when Adcorp entered talks to acquire the company.

The resulting deal swung open a number of new doors for Cooper, who became a key player in the restructuring of the staffing company’s South African operations. Adcorp, in turn, promoted Cooper into a group financial manager role before asking him to relocate to Australia to serve as the region’s finance leader.

It wasn’t long before Cooper’s purview spanned all of Adcorp’s Asia-Pacific operations, a charge that eventually led to him developing relationships with a variety of technology services providers—one of which was Reveal Group. –Jack Sweeney

Gillian Sheeran’s was perhaps 17 years into an illustrious finance career and on her second CFO tour of duty when she finally met the limits of her CFO superpowers.

These powers had first guided her into a CFO role at the tender age of 32, where during her tenure she would help to turn a 200-employee IT consulting firm into a global business with 850 workers and eight offices in six countries. Next, she added a turnaround chapter to her CFO resume when she helped to design and implement new processes allowing a company to return to profitability within only 9 months.  

It was such stirring feats and results-oriented outcomes that led a mentor impressed by her resume to comment, “You’re going to have to take half of this stuff out because nobody is going to believe that you did all of this in such a short period of time.”

To help us better understand the career mind-set that once guided her thinking, Sheeran issues a mock impression of herself: “I work incredibly hard because that’s what I do—I work smart, and I work hard, and I go in and achieve, and I never fail.”

To which she adds: “I thought I was invincible because I used to be able to sleep.”

She explains: “Monday to Friday, I might have slept 4 hours—or some nights, even worked straight through—but I could always sleep on the weekend. But now, with kids, I could no longer sleep on weekends.”

Of course, we know that more than sleep—or the lack of it—is responsible for altering Sheeran’s career mind-set. It was during her turnaround CFO chapter that Sheeran, then the mother of a 2-year-old and a 9-month-old—encountered experiences that she had never run into before.

Sheeran recalls: “I ran into a wall—and I never run into walls.”

There were days, Sheeran tells us, when she found herself unable to answer emails. This is a frank admission that Sheeran uses to expose what now appears to be a turning point in her career.

“The experience made me redefine who I was and how I was going to do my job going forward—and unfortunately I had to learn by failing,” explains Sheeran, who would step down as CFO and vacate the professional world for a period of 2 years, during which the pandemic arrived.

Along the way, as Sheeran’s oldest child reached school age, she and her husband agreed that her home front status need not be a long-term plan.

Reports Sheeran “I may be a great CFO, but I’m not great when I’m home with the kids all day.”

Last January, as she began evaluating opportunities for returning to the C-suite, Sheeran listed market potential, fast growth, and smart people as the most requisite characteristics of a business that she would like to join.

In addition, she wanted a workforce culture and set of values that she could “get behind,” before adding yet one more business characteristic to her wish list: “flexibility.”

Comments Sheeran: “I really wondered whether I was pushing the boat too far.”

In July 2022, Sheeran was named CFO of Pricefx, a fast-growing pricing software company that she credits with having checked every box on her list.

Indeed, flexibility soon turned out to be a very important box when the date of Sheeran’s daughter’s first day of school in late August ended up being scheduled to coincide with a Pricefx strategy meeting—which quickly landed elsewhere on the calendar.   

Remarks Sheeran: “We believe in family, and it’s not just lip service.” –Jack Sweeney 

If, as the old maxim suggests, “life” is what happens to us while we are busy making other plans, Adil Syed’s other plans most likely did not include Snap Inc—or at least they didn’t when he first headed east to attend business school.

Having spent the previous 3 years at Redpoint Ventures helping to raise capital for such tech gladiators as Stripe and Zendesk and 5 more at Goldman Sachs as a financial analyst, Syed was ready to have a typical business school experience in which he’d spend his days going to class and nights attending gatherings with classmates.

Sure enough, this was how Year 1 of Syed’s business school experience unfolded. It was during his second year, that he stepped into a role that would arguably become the most consequential of his finance career.

“I was the first summer intern at Snapchat, which at the time had only about 100 or so engineers and appeared to me to be such unique place that eventually I decided to join them full-time,” recalls Syed, who notes that the opportunity to work for the Venice, California-based company was worth all of the complications that it brought.

“My second year of business school consisted of me working full-time in Venice while flying back and forth to complete my classes and graduate as best I could,” reports Syed, whose professional life suddenly faced a challenge unlike any that it had yet encountered.

“We had a billion dollars of venture funding in the bank,” he remembers, “and the app was growing like we had never seen before. Yet there was no real business model. There was no financial rigor. There was no forecast to tell us how to sell and monetize the app.” Over the next several years, Syed would serve in a series of finance, strategy, and operations roles at the company.

Less than 2 years after his arrival at the company, Snap went public and increased its market value by nearly $9 billion on its first day of trading. More than 200 million shares—the entire size of the offering—changed hands over the course of the day making the Snap IPO a big day on the tech industry’s calendar of Wall Street milestones.

The historic IPO would fall roughly midway into Syed’s Snap career chapter and provide set of experiences that Syed says offered as many finance leadership lessons after the IPO as he had learned before. “This was a start-up that went from 100 employees in 2015 to 3,000-plus by 2019—It challenged my perspective on how to grow and scale systems, processes, and people,” he explains.

“Ultimately, performance has to be coached, managed, and mentored, and there has to be a partnership,” observes Syed, who believes that while he originally performed poorly as a finance partner, along the way he learned how partnership depends on finance becoming part of the “operating fabric” of the business.

Concludes Syed: “I learned that the hard way. I probably failed more than I succeeded at first, but then hopefully I finally got it right.” –Jack Sweeney

It was after Ross Muken had been gainfully roaming the corridors of equity research for more than a dozen years that the acquisition of his firm administered a dose of operations insight that began to feed his aspirations to become a CFO.  

At the time, Muken was a top research analyst for ISI Group, an independent, research-driven trading firm that had begun to attract the attention of a number of the investment banking world’s largest banks—including Evercore, which in August 2014 acquired ISI and its 28 research analysts covering 345 companies in 10 major industry sectors.

“It was through this process that I saw what needs to happen when you integrate two businesses and need to drive cost synergies and margin expansion,” recalls Muken, who that point was helping to spearhead the firm’s healthcare and life sciences realm, an area of research that was enjoying some added luster due to a recent boom in biotech.  

Along the way, Muken says, it became apparent that the 20-plus-percent operating margins that management was targeting for the newly merged entity would be a bigger challenge than expected.

“It couldn’t just be the cost side of the equation—what was going to get us there was new revenue streams,” remarks Muken, who reports that the firm began evaluating possibilities in a number of untapped “adjacent markets” before formulating a strategic investment inside the equity capital markets business.  

“We had committed to the Street that we’d meet these margin targets, so putting in additional costs didn’t feel great, but our view was to be tactical and take some cost out but then reinvest those dollars to achieve higher margins,” comments Muken, who doesn’t hesitate to share the outcome.    

“This paid back tenfold, and we were able to build a very large revenue base with better margins in this new business, which allowed us to get to our margin targets without shrinking headcount,” says Muken, who today credits the tactical move with more than margin expansion.

He explains: “We had to take a strategy that made sense on paper and then have it make sense to shareholders from a numbers standpoint—and it was because of this experience that I decided to move to the operations side of things.” –Jack Sweeney

Brett & Jack discuss how hiring challenges have led certain organizations to be more tolerant of poor employee behaviors – a development that could be putting growing numbers of businesses at risk. Meanwhile, Brett points out that new hires continue to fetch bigger salaries creating an imbalance with existing employee salaries. Also, performance is not driven by talent alone. Brett says product issues are sometimes thought to be talent issues leading management to put in motion a string of misguided remedies.

This episode features the workforce insights and commentary of CFO Asil Syed of Rippling, CFO Ambereen Toubassy of Airtable, CFO Bryan Morris of Demandbase.

Inside the world of trade associations, the135-year-old American Coatings Association’s has never wavered in its dedication to advancing the needs of professionals inside the paints and coatings industry.

However, ACA members—like those of many associations these days—are becoming increasingly demanding when it comes to the value that they receive in exchange for their dues.

“In the old days, belonging to an industry association was a badge of prestige, and it was something that people felt that they just had to do if they were part of an industry,” comments Ilana Esterrich, who was named ACA’s CFO in 2019 after having served as chief administrative officer for a Washington think tank and spent the previous decade among the financial planning rank-and-file of Thomson Reuters and General Mills Corp.

Upon her arrival, Esterrich was told that to better address the escalating demands of ACA’s membership, she needed to clean house—beginning with the accounting department, which seemed to be a province populated by known underperformers.  

“I came in thinking that this was going to be a turnaround situation, and it was—but not in the way that I think management thought that it was going to be,” reports Esterrich, who after assessing the “skills and wills” of her accounting team members rendered a verdict of “not guilty” on all counts. It turned out that instead of being based on malfeasance, the accounting department’s laggard reputation was rooted in dated systems and processes—a set of circumstances that she and her team have since taken steps to correct.

Meanwhile, Esterrich discovered that a number of the association’s traditional sales practices involving media needed to be updated in order to be able to provide the sales team with better guidance when it came to determining if and when a customer could receive a discount.

No unlike most associations, ACA has long published a membership magazine, which Esterrich was told operated profitably.

“However, when we took a ‘fully loaded’ look at the costs of the magazine, we were upside down in the red,” recalls Esterrich, who sought to distance ACA from associations that choose to view the price tag of their member magazines as a necessary evil.

Says Esterrich: “Finance needed to show where the magazine brought value and where it did not—and at what cost.” –Jack Sweeney

Among the recruitment milestones that populate Bryan Morris’s CFO resume, few can match the 6-month talent acquisition binge that he launched during the first quarter of 2015.

“In terms of key hires, I never hired faster than I did then,” comments Morris, as he begins to lay out the circumstances that led to his need to speedily attract and hire talent.

At the time, Morris was the newly appointed CFO of Xamarin, a creator of software tools used for mobile apps development.  

This firm, then led by cofounder and CEO Nat Freidman, had doubled its revenue annually for the previous few years yet had theretofore focused its talent recruitment efforts mainly on nabbing software engineers and intrepid salespeople.

“When it came to people, sales, marketing, and R&D were way out ahead of G&A, so I knew that my first few months would be dedicated to recruiting,” recalls Morris, who notes that until his arrival, the developer had outsourced its accounting function while relying on fractional CFO services to patch any management voids.

“I made five key hires—head of HR, head of technical recruiting, controller, head of FP&A, and our first corporate counsel—all within the first 6 months,” remarks Morris, who believes that hiring can at times benefit from its own momentum.

He explains: “Sometimes, when you’re in a great situation and your company is growing, the press is great and the buzz is good—and what happens is that one great hire begets another. So, I kind of had this pinwheel going.”

Still, what happened next made Morris’s energetic hiring spree all the more consequential. During the second half of 2015, as Xamarin was preparing for another capital raise, Microsoft—one of the developer’s strategic partners—acknowledged that not only would it be willing to serve as a reference on behalf of Xamarin for the venture investor community but also it might be interested in partnering with Xamarin to pursue something more strategic.  

Subsequently, 12 months into Morris’s CFO tenure at Xamarin, company management signed a letter of intent (LOI) to sell the business to Microsoft. Looking back, Morris doesn’t hesitate to expose some of the drama that preceded Microsoft’s signed LOI.

“Here were my team and I—with only some 3 to 6 months of working together—and suddenly we were up against one of the most capable technology buyers in the world,” remembers Morris, who today believes that the timing of Xamarin’s key hires and the timing of the deal were not unrelated events.

“I couldn’t have done it by myself,” observes Morris, who points out that there were a number of 20-hour days during the period leading up to the finalization of the deal.

Morris notes that the merger provided mostly great outcomes for both investors and Xamarin employees—not excluding CEO Nat Friedman, who until late 2021 served as CEO of GitHub, which Microsoft had acquired in 2018.

Looking back on the CEO who hired him and the subsequent “pinwheel effect” that within 6 months transformed Xamarin’s lines of functional management, Morris highlights a shared mission: “Luckily, Nat was completely on board—he knew what I was inheriting, so he gave me the green light to go ahead and hire.” –Jack Sweeney