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    Business

    CFO THOUGHT LEADER

    CFO THOUGHT LEADER is a podcast featuring firsthand accounts of finance leaders who are driving change within their organizations.
    We share the career journey of our spotlighted CFO guest: What do they struggle with? How do they persevere? What makes them successful CFOs? CFO THOUGHT LEADER is all about inspiring finance professionals to take a leadership leap. We know that by hearing about the successes — (and yes, also the failures) — of others, today’s CFOs can more confidently chart their own leadership paths across the enterprise and take inspired action.

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    Copyright: © Middle Market Media LLC, 2019

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    Latest Episodes:
    Employers Dropping Degree Demands - A Workplace Champions Episode Apr 22, 2022
    Show notes

    Brett & Jack discuss why a 4-year degree isn’t quite the job requirement it used to be and how finance leaders are reworking their company’s talent equation. Featuring the commentary and insights of workplace champions CFO Brandon Maultasch of Moloco, CFO Steve Vintz of Tenable and CFO Kent Kelley of Unanet.


    794: The Customer’s Many Experiences | Will Johnson, CFO, Iterable Apr 20, 2022
    Show notes

    Will Johnson can still hear the question that momentarily muted a management dinner and prodded the gathering’s executive diners to thoughtfully dispatch an answer.

    “’If you weren’t in your current role, which one—held by a peer at this table—would you assume?,’” recalls Johnson, echoing the inquisitor’s words.

    “There were some really surprising answers,” he continues, noting that the head of sales expressed a desire to lead HR.

    Still, no answer was perhaps more surprising to Johnson than his own.

    “I actually did cite the CFO role,” comments Johnson, who even now—after having subsequently held three consecutive CFO positions—seems to be a bit surprised at his willingness to supply such an answer that evening.

    At the time, Johnson was a senior corporate development executive—albeit with future CFO aspirations but until that night they had been left unspoken, at least in gatherings.

    Johnson reports that there was a period in his career when he found it difficult to admit to himself and others that the CFO role was becoming accessible to him.

    “Shame on me! I still had in my head an antiquated notion of what it took to become a CFO,” remarks Johnson, who credits a CFO mentor who entered the office from the more traditional CPA route with having dissuaded him of the notion that he too needed to be a CPA.

    “The role’s orientation itself had really shifted to where you were spending as much time looking out the windshield as you were in the rearview mirror,” observes Johnson, who mentions that he’s speaking specifically of venture-backed and high-growth firms.

    If Johnson left the dinner with any doubts about having voiced his answer that evening, they likely vanished 6 months later when the company’s CEO, accompanied by a board member, approached him to be the company’s next CFO. –Jack Sweeney


    793: When Timing Matters | Adriana Carpenter, CFO, Emburse Apr 17, 2022
    Show notes

    As we seek to highlight the milestones that mark the path to the CFO office, one of our favorite queries is to ask finance leaders to recall from their career-building years the first time they presented to their company’s board.

    For Adriana Carpenter, memories of that board gathering will forever call to mind ASC 606, the mazelike revenue standard that only a few years ago upended the placid temperament of many an accounting organization.

    “Make no mistake—this was really my first time, and I was delivering bad news,” recalls Adriana, who perhaps not unlike many of her CFO peers received her first “invitation” to address the board regarding a sticky issue, rather than to highlight the anatomy of a strategic win.

    “A majority of our revenue came from on-premises software subscriptions, and 606 dramatically changed the timing of revenue for these types of subscriptions,” continues Carpenter, who for 8 years served as chief accounting officer for Ping Identity, a developer of identity security software.

    For Ping, the timing issue meant that the company would be required to take a big cash hit on the eve of realizing its goal of selling shares to the public.

    “606 distorted our revenue and EBITDA numbers, which really forced us to figure out how to explain to investors what was really happening in the business,” comments Carpenter, who entered the boardroom that day with a portfolio of accounting experience that any board worth its salt would have savored.

    Carpenter had arrived at Ping 5 years earlier, just as the company had begun the tricky journey from being a perpetual revenue model to evolving into the subscription revenue mode.

    “Within that first year at Ping, I led the complete overhaul of our quote to cash process, which included everything from revamping how we were selling our software to helping to implement additional software modules to enable the business to scale,” remarks Carpenter, whose tenure as Ping’s CAO involved navigating not only the differences between revenue models but also the differences between owners as Ping went from VC to private equity ownership.

    Then came 606’s timing issue and Carpenter’s invitation from the board. While milestones along the path to the CFO office frequently vary as far as time and place go, Carpenter’s arrival inside the CFO office at Emburse within 3 years of having received Ping’s boardroom invitation makes us think that perhaps timing is indeed everything. –Jack Sweeney


    792: Blazing the Cash-to-Crypto Path| Chris Roling, CFO, Coinme Apr 13, 2022
    Show notes

    Reflecting on a finance career that has spanned nine different countries and three decades, Chris Roling says that he may have received his most valuable career lesson at a plant in Pennsylvania’s Amish Country.

    As a newly minted MBA, Roling was hired by Armstrong Industries in the late 1980s to augment the finance executive ranks of its growing European operations. However, prior to dispatching its new hires abroad, the giant building materials manufacturer based in Lancaster, Pennsylvania, made certain that its executives got a generous helping of local operations.

    “It was reverse culture shock,” comments Roling, who served as controller of an Armstrong plant in Marietta, Pennsylvania, for 24 months before garnering a European assignment.

    Growing up, Roling—the son of a navy doctor—had had an aptitude for learning foreign languages, a talent that had led him to set his sights on a career in international business. Now, the Marietta plant was all that stood in the way of the young executive being able to realize his ambitions.

    “I thought that this was beneath me—I thought that I was a hot-shot MBA,” explains Roling, who says that the role involved leading a team of about eight accountants ranging in age from 18 to 58.

    “I was Immediately humbled. They taught me how to do the job, how to manage, and they taught me how to be a leader,” recalls Roling, who credits this experience with providing him with “many dividends” after his career took him overseas.

    Still, Roling says, his greatest lessons at the Marietta plant came from a “crusty, old” plant manager, who insisted that Roling regularly visit the plant floor.

    “It got to the point where I would see the plant manager coming in my direction and I would escape out the office’s back door in order to get down to the plant floor,” reports Roling.

    “What he reinforced was that the product was the heart of everything—and how that product was made and the issues that related to quality and productivity were things that I had never learned in grad school,” remarks Roling, who says that he later realized that the plant manager had also provided him with an important lesson related to finance and business partnership.

    Years later, while working abroad, Rolling says, it was his turn to be persistent as he sought out business partners in different parts of the organization who could provide “dedicated, knowledgeable, on-the-spot insight” and, on occasion, perhaps, an invitation to visit the plant floor. –Jack Sweeney


    791: Collaborating With Parts Unknown | Kent Kelley, CFO, Unanet Apr 10, 2022
    Show notes

    We have spent many hours in discussion with finance leaders about the intersection of finance and sales as we try to better understand the professional collaboration required to achieve successful outcomes in these domains.

    Still, few of our talks have pushed us to ponder the human elements and relationships that point to such success more than that with finance leader Kent Kelley.

    From the very start of our discussion, we quickly typecast Kelley and brashly concluded that here was a mild-mannered voice of reason that had sat across the table from some of the software industry’s most energetic sales titans. To be clear: Kelley—a 15-year Oracle veteran whose finance career had spanned operations, sales, and marketing—had never been a bookkeeper, and his consistent willingness to assume career risks along the way set him apart even more from his more traditional finance peers.

    It was just such a risk attached to a challenging new role that finally led Kelley to move outside of Oracle’s wide-body finance function altogether to join the management team of one of Oracle’s standalone business units dedicated to industry applications.

    “I moved out of my office overlooking the Oracle pond to a smaller office in San Francisco—I’m sure that some of my friends in finance thought that I was crazy, but I was stepping out of my comfort zone and really challenging myself,” explains Kelley, whose move to the business unit also led to a fateful collaboration with an executive by the name of John Andrus.

    Andrus, a passionate and seasoned sales leader who had been given global responsibility for the business unit, made it clear that his plans involved broadening Kelley’s responsibilities.

    “This was someone who had enough faith in me to say, ‘Hey, this organization is growing, and I need to focus on growing the rest of the world, so I need you to be my guy in North America,” comments Kelley.

    This would not be the last time that Andrus included Kelley in his future plans. A number of years into his new role, Andrus was recruited to be CEO of a company known as PowerPlan, and he asked Kelley to join the firm as CFO. After a “thorough” interviewing process with the company’s board, Kelley was named CFO in 2011.

    “We doubled the size of the company within our initial tenure,” says Kelley, whose CFO career took a dramatic turn when Andrus was diagnosed with stage four brain cancer and then shortly thereafter passed away.

    “I was suddenly leading the company,” recalls Kelley, who was named interim CEO of PowerPlan in late 2014. “Having to interact with the other executives at a level on which I had never interacted before led me to understand their respective challenges in a way that I had never experienced.” Kelley would continue as interim CEO until the sale of the company to private equity firm Thoma Bravo in 2015, at which time he reassumed his CFO position.

    Reflecting on his dynamic collaborator, Kelley remarks: “John was an experienced leader and a great mentor as well as friend to me.”

    While Kelley does not recall for us the first time that he sat down across a table from John Andrus, we can assume that the dynamics of the gathering would have been much the same as those at any other meeting between Oracle finance and sales professionals, representing a confluence of both mild-mannered and passionate voices resounding together in pursuit of a successful outcome. –Jack Sweeney


    790: The Correct Order of Things | Sarah Blanchard, CFO, Udemy Apr 06, 2022
    Show notes

    Back in 2014, when Sarah Blanchard became committed to landing her first CFO position, she kept a key criterion in mind: Her future company had to be mission-driven.

    “I ended up in digital health before anyone really knew what digital health was,” explains Blanchard, who received her first CFO appointment from Omada Health, an early-stage health tech firm whose flagship product at the time was a diabetes prevention offering.

    “When you talk about a mission that can have a huge impact on the world and a huge impact on humanity and our economy, this was something that I felt lucky to be a part of,” comments Blanchard, who admits to having had limited experience prior to Omada when it came to raising capital and being face-to-face with investors.

    “I had two choices: I could raise money from life sciences investors or I could raise money from tech investors, and they both tend to be creatures of habit—they like to see patterns,” observes Blanchard, who still seems to savor the dual challenge of opening the minds of two distinct groups of investors.

    Notes Blanchard: “I would spend lots of my time in trying to help life sciences investors understand how and why we could scale a healthcare company so quickly and at the same time help technology investors understand why ARR was not a metric for us, even though we were selling into enterprises.”

    Meanwhile, Blanchard’s tenure at Omada endowed her with a degree of extra vigilance when it comes to company pricing models.

    “Omada had an outcomes-based pricing model—which was really novel at the time—meaning that we didn’t really make any revenue if we weren’t driving outcomes,” explains Blanchard, who adds that the model was flawed due in part to the firm’s assumption that the number of lessons completed by participants was a worthy “milestone” and indicator of positive outcomes.

    “We were focusing on driving people to complete lessons, but lesson completion, while it’s correlated with weight loss, it is not weight loss, and it is not a reduction in the risk of getting diabetes, which is what we were all about,” recalls Blanchard, whose efforts to repair the model ultimately involved tasking the company’s data scientists with a mission to better expose the connection between participant weight loss and outcomes.

    Says Blanchard: “After we switched over to a percent-weight-loss-per-month model, we began getting paid for real outcomes.” –Jack Sweeney


    789: Always Be Hiring | Jonathan Sides, CFO, Fleetio Apr 03, 2022
    Show notes

    Among the many SaaS CFOs with whom we have spoken, few have listed their finance leader priorities for us as simply and concisely as did Jonathan Sides, CFO of Fleetio, a Birmingham, Alabama, software company that helps companies to track and manage their fleet operations.

    “My personal defect is always wanting to take on more—without realizing that I should actually be giving away my LEGOs and finding people who can do things better and faster than I can,” explains Sides, who labels his first CFO priority as “Always be hiring.”

    According to Sides, between 60% and 80% of Fleetio’s workforce lived in the Birmingham area prior to the pandemic—but now the percentage of local employees has dropped to less than 50% as the company has actively recruited more remote workers.

    Next, he advises CFOs to work closely with the company’s investors to help them to understand the challenges that a company may be facing.

    “The only way that they can help you is if they have the unvarnished truth,” comments Sides, who notes that investors will typically have three responses: “They’ll say, ‘Don’t worry, this is normal’ or ‘Don’t worry, we know how to fix this’ or ‘Good luck, we know that you know how to fix this.’”

    The third and last priority that Sides lists is “Achieving work/life balance”—an area, Fleetio’s CFO tells us, with which he has long struggled and that in the past has led him to take some inspired action.

    Back in 2014, prior to joining Fleetio and having just completed a 14-year tour of duty as CFO of another Birmingham SaaS firm, Sides scheduled a “gap year” for which he and his wife bought “one-way air tickets” to kick off 12 months of travel during which they lived in 12 different countries.

    Still, all roads eventually led back to Birmingham and, of course, the SaaS model. –Jack Sweeney


    Hiring for Hypergrowth | A Workplace Champions Episode Mar 31, 2022
    Show notes

    Brett & Jack discuss how finance leaders of high growth firm’s are becoming increasingly focused on the ebb and flow of their firm’s talent pipelines. Featuring the commentary and insights of workplace champions CFO Gina Mastantuono of ServiceNow, CFO Josh Siegel of CyberArk and CFO Sarah Spoja of Tipalti.


    788: When the Road Rises to Meet You | Emily Villatte, CFO, Acast Mar 30, 2022
    Show notes

    Emily Villatte’s finance career first got rolling along dusty country roads in the Australian bush. With a dual-track master’s degree in engineering and finance, she had been hired by British multinational JLT Group to provide risk management and insurance services to a cluster of accounts residing in Australia’s outback.

    Along the way, Villatte says, she was frequently greeted by the question, “What the heck brings you here?”

    It’s a greeting that Villatte is just as apt to hear today as she was back then. However, this time the road has taken Villatte into the world of podcasting, where today she is the CFO of Acast, a Swedish-founded company that provides hosting services for both podcast creators and advertisers.

    “Experience is what you get when you do something that you haven’t done before,” reports Villatte, who within 2 years of her arrival in Acast’s CFO office took the company public on the NASDAQ Stockholm exchange.

    According to Villatte, the finance team was more than ready.

    “We had taken the prep work as far as we could, so when the board made the decision to do an IPO, we had about 14 to 16 weeks to execute,” recalls Villatte, who characterizes Acast’s IPO as a milestone not only for the company but also for podcasting as a medium.

    “My job was to make certain that we had the options all set for an IPO and would be ready if the board decided to go down that road,” comments Villatte, who no doubt viewed that route forward as not very different from others that she been down before. –Jack Sweeney


    787: Listening to Your Inner Self | Steve Vintz, CFO, Tenable Mar 27, 2022
    Show notes

    Looking back on his first CFO role, Steve Vintz recalls waking up one morning and thinking that he might not have a job.

    The night before, Vintz had told his company’s CEO that he was having second thoughts about a deck of slides highlighting the virtues of a proposed acquisition.

    “It just hit me: This is a deal we can’t do—this is not our deal,” recalls Vintz, recollecting the moment of insight that he experienced and the subsequent butterflies set free.

    The company’s board was expecting to meet later in the week, and the “board deck” was the anticipated precursor to a presentation that Vintz and his CEO were preparing to give about a promising acquisition target.

    Vintz continues: “Good news travels fast and bad news travels faster, but I caught this a little late in the process. I wish I had felt this way earlier on, but it was a reality. CFOs must have conviction, and conviction is all about doing the right thing.”

    The courage of Vintz’s convictions were quickly put to the test when he told his CEO about his reservations concerning the deal—an acquisition that had already received strong support and enthusiasm from the firm’s management team.

    “The conversation did not go well. The next day, I called our CMO and asked if I should even come back into the office,” comments Vintz, who adds that the CMO encouraged him to return and speak further with the CEO, who appeared to have begun to digest some of what he had heard the night before.

    Days later, when the company’s board members gathered, the CFO was once more in the hot seat.

    Says Vintz: “The board wanted to understand why we were having second thoughts, and as we talked, it became clear to the CEO and management team why that was not the time to do this deal.”

    In the end, the company’s board ultimately praised the management team for bringing forth its concerns, and a few of its members even repeated the business maxim about how sometimes the best deals are the ones that you don’t do.

    Reflecting on his moment of insight, Vintz observes: “I could have very easily sent out the board deck and told myself, ‘I don’t want to look bad, and maybe it will be okay’—but as CFO, you have to listen to your inner self.” –Jack Sweeney


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