Everybody knows Jack

If 8:30am in a hotel conference room filled with well-dressed CFOs is the last place you’d expect to hear Metallica, then you’ve never seen Jack McCullough speak. In fact, much of a McCullough speech is…different than what one would normally see at a high-powered business conference.

To watch McCullough work the crowd during a conference is to really see him shine. At the 20th annual MIT Sloan CFO Summit in November, a conference he co-founded, McCullough moved from table to table for hours, attendees calling out to him as he moved through the room. There were over 400 CFOs and finance professionals at the one-day conference and, to an outside observer, it seemed like McCullough knew each one.

“I’m visible within that community because I’m the founder of that conference,” McCullough told CFO Brew recently. “And it was the 20th year; there’s just a comfort level that people have developed with me.”

But that’s not really surprising; one CFO who’s known McCullough for decades called him, “the consummate networker.”

“He just knows everyone…and that comes across in the work that he does. It’s a really powerful differentiator for him,” Michael Bayer, CFO of Wasabi Technologies, who met McCullough in the early 2000s, told CFO Brew. “He’s seen as the connector.”

As the founder and president of the CFO Leadership Council, a professional association with 2,000 members and 30 chapters across the US and Canada (with another opening soon in Las Vegas), author of two books, and a co-founder of the MIT Sloan CFO Summit, McCullough has been a tireless advocate for decades in helping CFOs transition from a technical, backward-looking accounting role to becoming more strategic, empathetic, and inclusive business partners and leaders.

“He really wants to build an excellent community of finance leaders that goes beyond the finance and accounting,” said Joyce Bell, CFO of JM Bell Consulting and a founding member of The CFO Leadership Council. “It’s really recognizing that the role of a CFO is very much of a leader, so you need to have emotional intelligence and need to understand what leadership and development is.”

In chapters across the country, members of the CFO Leadership Council hold networking events, and offer informational presentations by experts and local CFOs on a variety of topics including ethics, technical accounting, and leadership.

From the beginning, the group focused on two things that set them apart from other organizations, according to Bell and Bayer. First, they focused on developing soft skills over technical skills, and second, local member advisory boards drive each chapter’s content based on local issues and challenges.

Along for the ride

In many ways, McCullough’s career trajectory tracks with the seismic shifts in the CFO role in the last two decades. After studying accounting at Suffolk University in Massachusetts, he spent three years as an auditor at Peat Marwick, the predecessor firm to accounting giant KPMG. Seeking more challenges in his career, he moved into industry at Boston software startup Gensym as its controller.

“I found the business side of auditing more fascinating than the accounting side of auditing,” McCullough told CFO Brew. “At Gensym, I felt like I was building something and I did not feel that way in public accounting.”

At that time, the path to CFO was changing. In the mid-90s, especially in the tech industry, companies started looking for CFOs to take on a more strategic role.

“[That] was the first time the CFO was really becoming a center of not just thinking about one’s dollars and cents, but more about business strategy, articulating that in a difficult environment,” Bayer told CFO Brew. “The story was changing so quickly; the Internet was coming.”

McCullough said his ultimate career goal at that time was to become a CFO, and after five years at Gensym, decided he needed an MBA to bolster his resume.

After earning his MBA at MIT Sloan, McCullough worked a series of CFO roles throughout the Boston technology ecosystem through the early 2000s before returning to KPMG in 2010.

However, a side hustle was about to take off.

From the ground up

The CFO’s role was evolving full tilt in the 2000s. Regulatory changes in the wake of accounting scandals like Enron and the 2008 crash put new responsibilities and demands on the CFO, and CFOs were increasingly being seen as strategic business partners to the CEO.

For McCullough, navigating that rapid change at a smaller company was a growing challenge. Existing organizations’ finance professionals focused on larger companies, and the professional associations were more top-down advice than he wanted, he said. He decided that he needed a network of peers experiencing the same challenges to share with.

Looking to build that network, McCullough organized the first of what was then called the CFO Roundtable at a conference room at MIT in 2006. Expecting 20 people to attend, nearly 60 showed up for the first meeting, he told CFO Brew.

“I realized that, quite by accident, I touched a nerve,” he said. “I felt some comfort, knowing that there are a lot of younger CFOs struggling to figure things out in a rapidly changing world.”

The CFO Roundtable grew quickly. What McCullough originally intended to be an informal get-together four or five times a year turned into a monthly event. A steering committee of CFOs was formed to help develop programming for the group, and it became an important part of the Boston finance ecosystem, according to Bell.

“What differentiates it [is that] it’s by and for the members, versus a national organization creating all of the programs,” she said. “It is asking members, ‘What is it that’s top of mind for you?’ and creating programs around that.”

One of the early focuses for the organization was developing soft skills such as emotional intelligence, mastering difficult conversations, and ethics. McCullough and others in the organization realized that as the role was changing, the most successful CFOs were not necessarily the best accounting technicians, but the best leaders.

“We collectively realized that the soft skills were critical,” McCullough told CFO Brew. “I remember people rolling their eyes and saying, ‘What the hell are you doing? What does that have to do with being a CFO?’”

The org

But CFOs and aspiring finance professionals understood. The group grew organically throughout the 2000s, with chapters opening across the country, often spread by members moving to new cities. McCullough eventually changed the name to the CFO Leadership Council (CFOLC) and incorporated it, leaving KPMG in 2006 to run the CFOLC full time. McCullough sold the CFOLC in 2021 to the Chief Executive Group (CEG), a publishing and events company, but remains its president.

With its new partnership, CFOLC has ambitious expansion plans, including opening international groups, according to McCullough.

McCullough’s own remarkable soft skills are driving much of that expansion, several people who have worked with him over the years told CFO Brew. Colleagues describe him as an empathetic, energetic, and compassionate leader.

“He’s very thoughtful, very collegial and collaborative in a difficult environment, because he’s trying to corral sponsors and CFOs and thought leaders,” said Bayer.

Stephen Gregorio, CFO at Tomorrow.io. Gregorio hired McCullough for his first finance job after he left public accounting and has watched McCullough grow as a person, a CFO, and as the leader of the CFOLC.

“He’s been an amazing asset for people like me and others that want to get more information about what’s happening in other parts of the finance world,” said Gregorio.

In his late 50s, McCullough knows he won’t be running the CFOLC forever. But the community, and the energy he derives from it, still motivates him to help make CFOs better and he still feels that he has a lot of work to do.

“We as an organization have a responsibility to make sure that women have leadership opportunities,” he said.

The CFOLC has launched several mentorship and diversity programs to support women and finance professionals of color, including the Ascend program, which supports underrepresented groups with learning and networking opportunities, and creating a DEI advisory board.

No matter how long he stays with the CFOLC, building a community, connecting with others, and boosting finance professionals of all stripes in their careers, has been worth more than a lucrative career as a CFO himself, McCullough told CFO Brew.

“I hope I won’t look back and say, ‘Geez, I wish I had a little bit more money in the bank account,’” said McCullough. “It was a decision I made: love or money, and I picked love, fool that I am.”—DA