In this episode of Careers in Finance on FinPod, we sit down with Jack McCullough, the founder and CEO of the CFO Leadership Council. Jack has had a diverse career that began with earning an MBA from the MIT Sloan School of Management and includes being a former CFO, a published author, and podcast host. His journey began in public accounting, later transitioning to leadership roles at tech startups. Jack’s background in finance ultimately led him to create the CFO Leadership Council, a community that empowers financial leaders across North America.

In this episode, Jack discusses the evolution of the CFO role, emphasizing how CFOs have shifted from simply reporting history to making history. He shares his insights on the importance of community building, mentoring future CFOs, and the challenges CFOs face today, such as managing talent and navigating rapid technological advancements.

Transcript

Anna Talerico (00:14)
Welcome back to another episode of Careers in Finance. I am so excited. This is a little bit of a special episode for us because we have Jack McCullough. Some of you may know him. What an incredible career you’ve had. will say as a little introduction, Jack is the CEO and founder of the CFO Leadership Council, which is how I came to know him. But he is an author. He is a podcast host, a fantastic podcast that we love here at CFI,

and he is a former CFO. Such an interesting career, Jack. Thank you for being here.

Jack (00:52)
Well, I love that introduction. Play that up as best you can. Thanks for having me. I mean, when you invited me, my first reaction was, she really want me? But I’m honored to be here. Hopefully, it will be a great episode for your listeners.

Anna Talerico (00:55)
Yeah.

Thank you, I’m so excited. So I’m gonna jump in, but before I do, just so everybody gets their bearings, can you do the just one- or two-minute overview of what the CFO Leadership Council is?

Jack (01:18)
Sure, we’re a professional association for senior financial executives. Some people see the name CFO and they wonder if like controllers and VPs of finance can join and absolutely they can. But our goal is simply to empower CFOs and we do that through a series of professional development programs and much more so than that, the network that we’ve created. One of the members and I can’t remember who it is, but I’d really like to attribute it to him. He said,

he told me once, I joined for the content, but I stayed for the community. And I think that’s why people are in the CFO Leadership Council. In fact, Anna, I’m sure I must have shared this with you at some point, but there is a period in May and June, there are like seven CFO conferences that happened at the same time, and the CFO publications cover them all. And so one publication said that our event was more like a family reunion than a business event.

And then another one said that we set the world record for hugs at a financial conference. But it’s that type of community. We have great programs, absolutely. I’m proud of the programs and the content. But it’s our community that stands out.

Anna Talerico (02:26)
Fantastic. I, everybody that I know that is a member, just speaks so highly of the experience and the community and what you’re doing. And I think maybe the way I first became connected with you is I tried to get in and you said, somebody said, no, no ma ‘am, you’re not a CFO or a controller or a VP finance. But luckily, it led to a fantastic relationship. I’m so glad to know you and the work that you’re doing.

Jack (02:45)
Yeah.

Indeed, well, Anna, I was a bouncer in college, so those instincts, back when a normal-sized person could hold such a job, and those instincts still are with me 40 years later.

Anna Talerico (03:06)
There you go. But that’s what makes it such a good community, right? mean, you’ve got such a, you know, they’re peers where I think it’s a safe space. You know, they don’t have the interlopers of vendors trying to sell each other things or, you know, non-finance roles trying to get in. So I think that’s probably part of the success. So,

let’s jump in where I usually start, but we’re gonna do the career part really quickly so we can get to founding the CFO Leadership Council and everything, but tell us how I always start the podcast is your origin story. Did you always know you wanted to go into finance and what did you study? So let’s start there.

Jack (03:45)
Yeah, I’m not sure that I really wanted to go into finance and accounting or that I even necessarily knew what accountants did when I picked it as a major when I looked back. you know, like a lot of my peers who were, you know, who entered the profession, I came from a blue-collar family, and I viewed college just as a place that I could get, you know, a good-paying job with some stability. you know, accounting seemed to be a pretty good place to do that.

And I’d say it was a good choice. I entered the workforce 35 years ago, a little bit more than that. And let’s say it’s 35 years. I’ve been employed 34 years and nine months out of the 35 years. And for people my age to talk to them, that was a big thing at the start of the career, that you just have a nice stable career path and have a good quality of life and make money. It’s an added bonus that I ended up being reasonably good at it.

And I found that I really liked doing it. I wasn’t a great natural auditor necessarily. I started with one of the big eight accounting firms. But I really liked climbing up and becoming a CFO and being a CFO for several years.

Anna Talerico (04:54)
Then it’s lucky since it sounds like it was not necessarily the choice out of passion, but just the right choice, right? For stability and for a good quality of life and everything. And then, yeah, yeah, yeah. So let’s talk about some of those first roles in your early career. You started in public accounting. And so just maybe take us through some of the first few roles that you had and you did the public accounting and then what was your kind of next role from there?

Jack (05:05)
Yeah, it served me well.

Yeah, sure. And I did exactly three years in public accounting. And I mean, it was like, three years and four days type of thing. And I did it at Pete Mourick and Mitchell, which your young listeners will know as KPMG. And then I left for a tech startup and that really led, that was a really good choice. Love my boss. We’re still friends to this day, all these years later. But that really led to my passion for being in innovative entrepreneurial types of companies.

Anna Talerico (05:24)
You.

Jack (05:50)
And it was a company that no longer exists. It was acquired. There was Jensen Corporation. But the interesting thing about Jensen, as far as we knew, it was the first company in history that was focused on artificial intelligence that was profitable. So it was started by a bunch of MIT nerds. And they’ll forgive me if they listen to this podcast, but it’s true. But it was called an expert system.

Back then, you couldn’t use the phrase AI because people were thinking of the Terminator movies and that Arnold Schwarzenegger was gonna come back in time and wipe us out type of stuff. Expert Systems was just a different way of saying AI. Had a successful IPO and it was a great time. And that set me up for a career-long passion for starting businesses.

Anna Talerico (06:40)
Wow, so you got to, when you joined, you were there through the IPO. So that’s, I always say going through things like that is like a crash course in a whole other set of things you never knew or learned before. You learn so much going through those experiences, I’m sure.

Jack (06:54)
Yeah, actually, I wasn’t the CFO who took the company public. So I, you know, did a lot of the prep work. Yeah, yeah. I saw the level of stress that the executive team went through, but, but yeah, it wasn’t exactly the same thing, but yeah, it was a great learning opportunity. And I did have a boss who was, like I said, real good guy, you know, genuinely took an interest in not only my, but his entire team’s career. And, know, there’s a reason he’s been a very successful CFO, you know, since then.

Anna Talerico (06:58)
But you got to be there through it though, right? Yeah, yeah, yeah. Yeah.

Jack (07:23)
You know, so I was exposed to a lot at a relatively young age. you know, when you think about it, like public accounting, I graduated college at 22. That’s a lot of responsibility for a 22 year old to go and audit like a publicly traded company. And then I worked at Jensen from when I was like 20, I’m going to say 26 to 31, something like that. And, you know, getting a company ready to go public, you know, that’s. You know, that’s that’s a lot of pressure, you know, so.

Anna Talerico (07:53)
Yeah, indeed. know. But a great experience to be witness to it for sure. Yeah. So when you left there, what was your next role after that?

Jack (07:56)
Yeah, yeah, time of my life.

I returned, I didn’t think I could get a CFO job, which is what I wanted, because it was good experience, but it wasn’t, you know, there are a lot of people who are controllers for companies, and I only had three years in public. So I decided to get an MBA, and I went to MIT Sloan, got that degree, and that was transformative, because, you know, putting MIT next to your name, I suddenly went in the eyes of people who didn’t know me very well.

I suddenly went from being a reasonably bright guy who had a good future to being some financial genius with an MBA from MIT Sloan. It completely changed the way the world perceived me. my sisters and my cousins would kind of roll their eyes at the whole concept that people viewed me that way, and my childhood friends too. But it was a great move. I learned a lot, made connections that I have to this day. And it just gave me a whole lot of credibility for my next opportunity.

I may have become a CFO through dumb luck, but I don’t think I would have. just, I don’t think I, if I just continued being a controller, that I would have become a CFO. So without that in me.

Anna Talerico (09:11)
The halo effect of the MIT Sloan Fellow, right? Is that what they’re called? MIT Sloan Fellows or something? Yeah. okay.

Jack (09:16)
Fellows is a particular program. It’s more for not mid-career but people who’ve worked for like 15 years. And it’s usually paid for, like they work for big companies and the companies pay for it. And you kind of, it’s like a year straight. It’s a pretty intense program. We used to joke, you enter when you’re 35 and a year later you graduate when you’re 50. You know, could actually see the gray hairs emerge in the classmates.

Anna Talerico (09:26)
Okay. Yeah, yeah.

Yeah.

Yeah.

Jack (09:43)
Hopefully Sloan, geez, I’m offending everybody now. Hopefully my Sloan people won’t…

Anna Talerico (09:46)
No, no, because don’t you do something with MIT Sloan still or you have after you graduated? Yeah.

Jack (09:51)
Yeah, yeah. started around 2002. I started the MIT Sloan CFO Summit. And that was around the time with the dot com crash and Enron and Anderson. And there wasn’t really, you know, there are a lot of them now, but there wasn’t really a high-quality conference for CFOs that wasn’t commercial in nature. So we sort of thought, you MIT, it’s, you know, it’s the intersection of technology, strategy, finance and leadership.

That’s the modern CFO, right? Who better to put on a CFO conference than that? And we just decided to do it. It was supposed to be a one-time thing. And 21 years later, I guess we were wrong on that. But it’s a great event. I mean, I’ve gotten to meet some of the best CFOs in the world because of that event.

Anna Talerico (10:26)
Yeah.

Incredible.

Yeah, incredible. you got your, went back to MIT, you got your second degree, and then what did you do next? What was the next role after that?

Jack (10:47)
I then worked for a company called Top Layer Networks. And I worked there for five years. was a venture-backed I was the CFO. I was something like employee 25. Grew the company from zero to around 60 million. And we’re going back a little bit. This was 20 years. And we had an acquisition offer that we didn’t take,

believing that there were companies that weren’t performing as well as we were, and they had market, they went public with a market cap of a billion dollars, and we thought we could do that. But then that little, that dot-com thing pulled the rug right out from underneath us. So, with hindsight, a lot of people’s lives would have been changed had we settled for 600 million. But it was a weird time because, like, I remember,

I remember these numbers. We had nine million in revenue and we lost $40 million, which is actually challenging to do, to have that much money. And to spend that much money when you only have nine million in revenue means you’ve got to spend about 50, right? How do you spend $50 million under those circumstances? So we lost $40 million. And back then, CFOs and VPs of HRs, had faxes in their office for the private stuff.

And I remember one day I got a fax with the signed term sheet valuing the company at $400 million. And it’s like, first of all, I was thinking how the heck, you know, it wasn’t a publicly known fax number, but like they just faxed over a term sheet and it had a signature. And part of me was thinking, is this a joke? It wasn’t, it was real, it was legit. You know, at hindsight, I should have just signed it. I was an office of the company after all. But yeah, it was such a perception that the bubble would never…

Anna Talerico (12:26)
Yeah.

Yeah, there you go.

Jack (12:42)
and bubbles, so far, they’ve always ended. Maybe the next one won’t, but so far they’re cycles. Generally, things are better, but they go up and down and then up again and down again.

Anna Talerico (12:42)
Yeah.

They do, indeed. So was it then when that wound down, was that when you decided to launch the CFO Leadership Council? tell us a little bit about, of fast forward as to what you were doing and how you came to decide to do this.

Jack (13:11)
Yeah, so what I did, I started a CFO practice where I decided just, you know, I had the money. There weren’t a lot of full-time jobs in the Boston area for CFOs because there were a lot of people with a similar story to me. You know, great story, raised a lot of money, had a lot of fun, didn’t get out before the bubble burst. So, you know, a lot of us like that. And I just decided I had my oldest son had just been born. So I just decided, you know, I’m going to.

Anna Talerico (13:15)
Mm.

Jack (13:39)
kind of do some stuff for myself. started a part-time CFO thing. And along the way, I just wanted a network of my peers. And just so I could, you know, learn from each other, build a community. I actually applied for a, I applied to join an organization, FEI. I’m sure you’ve heard of them. They actually turned me down, even though I lied on the application. But back then you had to be a public company CFO to join and…

Anna Talerico (13:59)
So.

Jack (14:09)
I didn’t really lie on the application. But, you know, they turned me down, rightly so, and according to their policies at the time. yet, I wanted a CFO peer group, so I started what is now known as the CFO Leadership Council. The original focus was just CFOs and venture-backed companies. I figured I can’t be the only one these folks have turned down. And, you know, I thought we’d get a dozen. And the first meeting we had, I had friends lend space just…

We didn’t have any money, so I called a friend of mine at MIT and said, can you give me a conference room for 25 people? And just through a bunch of emails, I said, spread the word. And we had like 60 people come. And if I was a cartoon, the light bulb would have gone over my head. And hey, this is a pretty good idea. A lot of people want the same thing as me. So I started doing that for a little bit. I was a part-time CFO running the CFO Leadership Council. I was developing. I got known as being well-connected.

Anna Talerico (14:47)
How?

Yeah.

Jack (15:06)
in Boston because of the council and because of the MIT event. And KPMG, my old friends, they called and they said they wanted to launch, not launch, but they weren’t much of a presence in the venture space and they wanted to be. So they wondered if I would run it. And I said, yes, I will. So I did that for five years and that was great. mean, public accounting was very different in the 2010s than it was in the 1980s. So it was…

Anna Talerico (15:33)
Sure, what a fun opportunity.

Jack (15:36)
Yeah, and was, you know, it really, it was a good experience. had, I love my boss. I’m amazing. Pat Canning, best leader I’ve ever worked for. he’s since he retired from the firm, he’s still active, but a really good guy. Just friendly, that type of thing. In fact, I, just the type of guy he was, he called me in. I went like, like, I went about 60 days, I didn’t bring in a client. And even though it wasn’t explicitly a sales job.

I know, his business developed and I still had to bring in clients. So he called me said, you know, I’ve noticed you haven’t brought in a new client in a couple of months. And so I said to him, Pat, that’s very astute observation on your part. And then I got up to leave. He’s like, what the hell are you doing? And I’d done stuff like that my whole life. He was the first one that ever stopped me from getting away with it. So, normally, that works, by the way. If someone gives you negative feedback and you don’t want to listen.

You just compliment them on the astute observations that they’ve made and walk out. George Kostyn, leave him laughing. Thank you. You’ve been a great audience.

Anna Talerico (16:35)
Hightail it out of there. There you go. It a fantastic experience. Going back to the 60 people that showed up when you thought maybe you’d get a dozen or so, that just really speaks to the…

power of connecting with your peers, I think, and the need for that, right? Just needing to be with others who are in similar situations. And so that must have just been like right there, you know, kind of, I’m sure very validating for you.

Jack (17:10)
Yeah, absolutely it was. mean, you know, we were a confident group, right? Even though the dot-com thing had happened, you know, we were all in the Boston area. You know, one thing about Boston, and I think any part of the country that has great schools, and know, Boston has 10 of them, you know, MIT and Harvard, the two best known, but there’s so many really good schools in the Boston area, we just always bounce back. You know, there’s just, we’ve got a bunch of smart young people.

They come here, they go to school here, they start businesses here. So even if it’s a little slow in Boston, it never lasts. So we knew it would bounce back. it was, in fact, my VP of marketing loves when I share this story, because it altered the history of it. Because it was kind of informal. I was just paying for everything out of pocket, but then as we got more and more people, I didn’t feel like spending $100, $150 out of my own pocket every month to feed people.

Anna Talerico (18:08)
Yeah.

Jack (18:09)
Not that I’m that cheap, but anyway, so what we did, I just put out a bucket and said, hey, if everybody can contribute a few bucks, I can pay for the catering, rent the room, that type of thing. Well, the second time I did that, the bucket got stolen. I’m pretty sure none of the CFOs stole money from me. But I don’t know who did it, but that forced a decision, so I actually started professionalizing the group. If the money hadn’t been stolen,

Anna Talerico (18:23)
What?

Jack (18:37)
there’d still be a bucket at the meetings today. Yeah, I went to Eventbrite. I hired somebody to sort of manage it part-time. I went to Eventbrite, started charging the meetings on Eventbrite, started dues and brought on a sponsor. But yeah, who knows who took it, right? I was gonna say it’s an accident, but I’m probably giving somebody too much of the benefit of the doubt. Someone…

Anna Talerico (18:40)
Well, what a blessing then, turned out, right? Yeah.

Jack (19:03)
If someone took it by mistake, why they open it and saw there was a bunch of cash, they should have returned it. yeah, stolen money forced me to change the business model into a profitable business. Yeah, absolutely.

Anna Talerico (19:08)
Yeah.

And look at us now, look at you now. Maybe that box of money will show up one day on your desk, you never know. So when did you decide, well I have something here, I’m gonna do this full time. just, yeah, tell us about those, so you’re doing this on the side, of, you know, doing the KPMG venture practice. Tell us about the transition to like, I’m gonna go all in on this.

Jack (19:21)
If you’re listening, I know who you are.

Yeah, it was the classic case of love or money. you know, because I really liked working at KPMG and not saying this in a boastful way, but if you’re good at business development for a large accounting firm, you know, there’s some good money to be made doing that. And it was, you know, I had close to perfect job stability, right? It’s the type of job, even if the economy slows down, you don’t get rid of productive salespeople. So I sort of felt like I could just

Anna Talerico (19:48)
M-mm.

To her. Yeah.

Jack (20:13)
keep doing this job that I liked quite a bit with good people and make good money till I retired. But I just really wanted to make the CFO Leadership Council my job. I’d never had anything that I was so passionate about professionally. What held me back is, you know this about me, Anna, but I’m the father of two special needs boys, which meant my wife wasn’t working and I was responsible for salary and benefits. But we talked about it, we decided to do it anyway.

And so I resigned to my boss, a good guy named Ed Sullivan, and he said, don’t tell anyone what you’re thinking of, give me 48 hours. And I’m like, he’s going to give me a counteroffer. I don’t want one. And he said, OK, the firm’s fully with you, but you probably don’t have 40 hours a week right away, right? And I’m like, no. And he’s like, here’s what we’re going to do. We’re going to ask you to work half-time. We’re going to cut your salary in half, but we’re going to continue to pay for your benefits completely

Anna Talerico (20:53)
Yeah.

Jack (21:11)
for a year. If at the end of the year, this you still want to do it, we’re going to support you doing it. But if it doesn’t work out, just come back at under your present terms, right? It took away you know, I’m an entrepreneur, entrepreneurs are inherently risky. He took away a bunch of the risk for me, didn’t he?

Anna Talerico (21:25)
Incredible.

Yeah.

That’s incredible. Like you and your family decided to take the leap and jump and then there was a net right there to help you make that transition. That’s incredible. Yeah.

Jack (21:39)
Yeah. Yeah, and that, you know, it’s, I didn’t ask him to do that, and bluntly, I wouldn’t have. It’s like, gee, you know, I don’t have enough hubris to ask for somebody to do something like that. Hey, can you cover my benefits for a full year while I pursue a job that I like more? Yeah, but, you know, they offered, and, you know, they knew me, though. I’d worked there five years. They knew that I’d give my everything to them, and

Anna Talerico (21:45)
Yeah. Yeah. Yeah.

Yeah.

And I’m gonna leave you at the end, yeah.

Jack (22:07)
but they also knew that this was just something I really was going to do.

Anna Talerico (22:11)
Yeah, yeah. What do you think, I’m curious, what did you love about it? You know, were you just an entrepreneur at heart? Were you loving the community aspect of it or just making your own path? Like what do you think was it that said like, had that burning passion in you?

Jack (22:27)
Yeah, I’ll say, like, I loved KPMG. I love the people. It’s an interesting place to work. I never liked business development or selling. I became good at it. You know, I’m pretty likable and, you know, I can sell to CFOs. I don’t know that I could sell to engineers or something like that. But, you know, I can talk to CFOs as a peer and assess what their needs are. you know, if there’s something that we can do to help them, I can,

you know, make that happen. But I never felt a burning passion to continue as a career business development person. What I really liked was I liked creating events and creating a community where future CFOs and first-time CFOs were learning because I, you know, I worked hard as they do too. But, you know, had I been born three years earlier, you know,

I got my job because it was the dawn of the dot com era. I got my first CFO job because there were an awful lot of CFO jobs out there. I didn’t know if that was gonna be once in a lifetime. And I said, you know what, we have an opportunity here with the veterans. We can actually get the next generation of leaders. We can set them up to enjoy the same success that we did. So that’s what I liked. And it’s still, as I’m in my 60s now, it’s still what kinda gets me up. I love working with the ones my age.

But like when someone reaches out to me and says they’re a mentor, they’re looking for a mentor, can I be that person for a while? Or, you know, I just need your advice. I think I’m ready for a CFO role. Can you help me? I just love knowing that I’m making an impact. And, you know, I’m not overrating what I’m doing. You know, I’m not, you know, it’s not like a food bank where I’m helping hungry people or I’m not curing a disease, but I’m making an impact on these people’s careers.

Anna Talerico (24:24)
Absolutely, you are. Yeah, I love it. wow. So, so I want to talk a little bit about the things that you see, you know, from your vantage point. But before we jump into that, you start, it’s regional, you’ve got people coming in, in the Boston area. Fast forward to today, not regional, obviously, you know, big membership base. Tell the audience with the listeners here a bit about the scale and scope of what the CFO Leadership Council is today.

Jack (24:24)
So that’s what I like.

Yeah, and you know, it’s almost, the version of me 15 years ago might not have recognized this because truthfully, when we first went to New York, a friend of mine who was in Boston, she moved to New York and there wasn’t, she really liked our group and she actually called and said, would you launch a chapter in New York? And I was working full time. I didn’t have the cycles to do it. So I said, I just, don’t really want to.

I’m too busy. said, I can, know, what I did is not that hard. I can certainly coach you through that. And, you know, so she was a CFO, she was busy, she didn’t want to do it. So she called me back a month later, said, look, I’m still kind of stuck. And as it turned out, my partner at the time, Becky Blackler, her husband lost his job. So she was looking to make more money. And I said, yeah, why don’t you launch New York and you can, whatever you make, you can keep.

And then that repeated in Philadelphia, and that was sort of the proof that this wasn’t a Boston thing, that before long we had chapters up and down the East Coast. Now we have about 2 ,600 members. We have 33 chapters. The chapters are all in North America, one in Toronto, the others in the US. We have members on every single continent except Antarctica. And Anna, I’m such a competitive person that I actually looked to see if there were CFOs on Antarctica,

on LinkedIn and I was gonna give them a free membership so that I could claim a member there. There were two listed, but they’re not real people as best I can tell. One is a fictional character and the other is actually from Siberia, but he was stationed in Antarctica. I’m not sure I understand exactly what was going on there. But you know, every continent, we have members in Africa, Asia, you know, not every country, but every continent for sure. And it’s, also have…

Anna Talerico (26:23)
Yeah.

Mm.

Yeah, yeah.

Jack (26:46)
two big conferences. This year we have the biggest tech expo for finance and accounting people. In fact, not only the biggest, but perhaps the only. It’s called FATE, Finance and Accounting Tech Expo. And there wasn’t a expo for finance and accounting professionals to evaluate every technology in their tech stack. One of my colleagues, R .D. Whitney, he reached out to the community and said, we’re just kind of curious what’s in the tech stack.

Anna Talerico (26:54)
Mm.

Jack (27:15)
And perhaps you wouldn’t have been as surprised as I was, but I was thinking we’d get 30 technologies. And we got a couple hundred, a few hundred as a matter of fact. So it’s like, geez, how can we help these people? And it turned out there wasn’t one place where you could evaluate all of them because big companies were doing their own thing. SuiteWorld for NetSuite, they have SuiteWorld, which is a phenomenal conference, but it’s only NetSuite products and whatnot, or Planful and…

Anna Talerico (27:35)
Hmm.

Yeah.

Jack (27:43)
all of the big places, they do their own thing. It’s kind of a user meeting. No one was doing something that anybody who wanted to participate could do so. So we’re having our first one. It’s going to be, we’ll probably end up with about 1 ,500 people there. It said, have you ever heard of the Javits Center in New York? Okay, yeah, well, we booked it at the Javits Center and that was announced to the leadership team. I was the only one who’d never heard of it. And they were looking at me like I was a peasant.

Anna Talerico (27:46)
Yeah.

Wow.

Of course, yes, it’s huge, yeah.

Wow, okay. It’s a great event space, huge conferences. I can’t believe you didn’t know it when they booked it.

Jack (28:17)
Yeah, am I like the only person that didn’t? But I guess I was most impressed. was watching the movie Ted 2, the talking teddy bear, and they were at a convention that happened at the Javits Center. So then I knew it was a big deal.

Anna Talerico (28:25)
Mm-hmm. Yeah.

When is that conference, by the way?

Jack (28:35)
It’s late October. I hope RD’s not listening because he’s going to punch me. I don’t know the exact date, but it’s a few days. It’s like that 28th, 9th, and 30th, something like that. it… cool. Yeah. Let’s… We’ve met rent in person, so that would be great if we can make that happen.

Anna Talerico (28:45)
Good, well I’m going to be in New York then so I’m definitely going to attend. Yeah. Great.

For sure, for sure. So, wow. So I think you said 33 chapters, is that right? Yeah, incredible. And from what started in Boston as much of a passion project, incredible. So you have a really interesting vantage point because you are a mentor to so many and you are so connected. I have a few questions. I guess the first is, what…

Jack (28:57)
Yeah, 33.

Anna Talerico (29:18)
How would you characterize what’s changed in the last 20 years for CFOs and those roles? Just so much, feel like in the last five or six years, things feel like they’re accelerating. But when you look back and kind of zoom out, what’s changed about the role and the function?

Jack (29:33)
Yeah, I have a tagline that I use on my podcast, and the tagline is CFOs no longer report history, they make history. I mentioned, well, I haven’t mentioned you, but I got my job for a number of reasons, but I was just a really good accountant. And back in the 1980s, I got mine in the 90s, but back then, that was the main thing they looked for. If you had a good sense of accounting and finance and whatnot.

You could probably get by as a CFO in a lot of companies. Since then, it’s become very different than that. The job has become strategic. The CFO is often the right-hand person to the CEO. And it’s the most cross-functional of any job in the country, except perhaps the Chief Human Resources Officer. So it’s really a strategic, cross-functional type of thing. And the other thing is,

I asked several VC and PE investors and board members and CEOs what their number one quality is for CFO. And I did this right as we were coming out of COVID. So I make it a slightly different answer today. You know, the answer reflected the time perhaps, but if I gave you 10 guesses, I’m gonna guess you wouldn’t guess number one. It was empathy.

Anna Talerico (30:59)
Wow, yeah, yeah.

Jack (31:00)
Right? Yeah, it was, it was, they were looking for someone who was, they wanted the CFO to be empathetic. And because they just sort of, the reasoning was, look, there are a lot of people who have the finance and accounting skills to make really good CFOs, but it’s the people skills, the leadership that really it’s going to set, you know, the serviceable CFOs apart from the elite CFOs. In fact, I,

nah, jeez, I hope I can remember this or I’m gonna embarrass myself. But I came up with a little acronym that these are the five qualities that great CFOs possess that I’ve come up with, and it’s trice. So it’s transparency, resiliency, inspiration, collaboration, and empathy.

Anna Talerico (31:49)
Love i., You did it too, on first try. That’s great.

Jack (31:51)
Yeah, I got on the first one. Yeah. Inspiration is an interesting one because, you know, a generation ago, would you have said, CFOs are inspiring, but they inspire two things. They inspire trust. People generally, when they hear something from a CFO, they generally think CFOs are, you know, straight shooters. She says what she means and she means what she says. And, you know, largely they inspire confidence too. You know, while the CEO usually is the head chair leader if one is needed

people, you know, if the company’s struggling, has a bad quarter and people looking for a reason to stay, they want to see that the CFO is enthusiastic.

Anna Talerico (32:27)
Hmm. Yeah, that’s so true. You’re right. Yeah, it’s interesting to this kind of strategic cross -functional position that it’s become. I was interviewing an FP&A leader on the podcast and he was mentioning how he views his team as sort of like the neutral party, meaning, you know, I actually really resonated with me because if I’ve got a problem in the business, I might be asking my individual leaders, but then I’m, I’ve got to kind of take what they’re giving me, whether it’s data, opinions and everything. And I’ve got to

take a more neutral perspective of it. And it’s always finance that’s the partner in is definitely a CEO running the business with the CEO and such a strategic partner there. But I think this idea that they sit in the intersection of all the functions and are the ones that filter and distill and can be a more neutral objective.

I think that really characterizes what I hear from a lot of people in CFO seed and FP&A as well, just this strategic evolution of the function. What do you think that CFOs today are grappling with or what challenges are they facing? What’s keeping them up at night in general?

Jack (33:37)
Yeah, you know, I say T&T team in technology. Sometimes I say talent and technology. But if you remember James Cavill, it’s the economy stupid. It’s the people stupid, right? It’s fundamentally it’s a people job still, you know. It’s how do you keep your team motivated? How do you, you know, what are the best practices in retention? How do you manage the multi-generational workforce? Because, you know, baby boomers

Anna Talerico (33:49)
Yeah.

Yeah.

Jack (34:07)
have different needs from Gen X. And you know, I’m a boomer. I’m extremely impressed with Gen X. I hope you’ve had a chance to work with them, you know because they’ll be running the world soon enough unless Gen ALPHA outplaces them quickly. you know, they’re a very impressive generation. But you know, their needs are different than what ours were. You know, for me, I was happy with being able to wear jeans and a polo shirt on Friday and a foosball table.

Anna Talerico (34:09)
Yeah.

Yeah.

Yeah.

Jack (34:36)
And you know in cash and stock options but they’re a little bit more sophisticated and nuanced than we are. So it’s really working on the talent because it’s hard, because you know particularly young people but everybody

Anna Talerico (34:44)
Mm.

Jack (34:49)
They have so many opportunities, right? If you can’t keep them happy for very long and you can’t keep them challenged and motivated, you run the risk of perpetually losing them. No way to build a business. And then technology, know, good luck keeping up with the revolution in technology. I don’t know what the next big thing is going to be in 25 and 26, but there’s a really good chance I haven’t even heard of it, much less envisioned how it’s going to impact things. I don’t know about you, had you heard of generative AI until it kind of went mainstream?

Anna Talerico (35:19)
No, and was overnight, you know, and then suddenly all the talk of how it’s going to impact all the roles. So yeah, no.

Jack (35:26)
Yeah, absolutely. Yeah, I hadn’t. was one. And this is what we do for a living, right? I mean, and by the way, I worked for an AI company in the 1990s. I was probably more interested than most people, but I’d never heard of generative AI. And then all of a sudden someone’s telling me about they found this tool called ChatGPT and they used it to explain to their child that they lied about Santa Claus. And how can I tell my child that I’ve been lying and doing in a way that I don’t lose trust?

Anna Talerico (35:30)
Yeah.

True. Yeah.

Jack (35:54)
And I’m like, what a stupid technology. Who wasted their time on that? Little did I know, right? So don’t invest in technologies that I tell you to, because there’s a lesson there. But it’s really, keeping pace with technology. Back in my day, technology was reduce cost, increase a little bit of efficiencies. But now it’s the long-term competitive advantage. You’re not going anywhere without a thoughtful digital strategy. By the way, I mentioned Gen Z.

Anna Talerico (36:03)
You.

Yeah.

Jack (36:22)
You know, good luck getting them to come work for you if you don’t have a good digital strategy. They grew up with this. You know, I mean, I have a niece, she teases me all the time and, you know, she’s like, did you, you know, did you do accounting on stone tablets at the beginning of your career? So I’m not quite that old, but yeah, I did have the big green paper, you know, the, 14 column things and stuff like that, but yeah, she can’t even envision how hard that job would have been so.

Anna Talerico (36:29)
So true.

With an abacus. Yeah, with an abacus. Yeah, yeah.

So, final question for you, which is what advice do you give to people that are starting out their career and they are thinking, you know, CFO is the path that they want to be in. Like what advice would you give them?

Jack (37:06)
Yeah, it’s hard for me to give one bit of advice. You know, I definitely encourage people, find a mentor. And, you know, it’s fairly easy to do because there a lot of people that want to help you. Like we have a mentor community. And one of the struggles like a lot of our members are women of color

and they would like a mentor who’s also a woman of color because they’re looking for somebody who has conquered some of the challenges that they’re going to be facing. And that’s very difficult right now. You know, it’s a racial thing. Like I remember, I started at Pete Maurek. My class in Boston was like 102. I can’t remember.

I’ll go, best of my memory, we didn’t have like an African American in the 102, right? I vaguely recall a couple of people of Indian ancestry and a Japanese member. I don’t remember everybody and there could be somebody I’m forgetting, but it’s a different world right now. But the point that I got off track of, for people who want a mentor who’s got the same demographic background, it might be difficult if you’re looking for one who’s 50. So look for the mentor. And by the way, I found young

Anna Talerico (38:20)
Yeah.

Jack (38:24)
people, they can reverse the mentorship relationship. I have a reverse mentorship. It’s a Gen Z person. I’d learn as much from her as she does from me. Don’t tell her that if you ever meet her. But she’s very smart and they’re the future. They’re our future customers and members. And I’ll probably be retired by the time they’re running the world. But if you’re in your 40s and 50s, they’re your future bosses, very likely, at some point. So get to understand that cohort really well. And you can sell yourself that way.

Anna Talerico (38:49)
Yeah.

Jack (38:54)
I’ll help you understand my generation. share the wisdom that you’ve done. And the other thing is, you know, find your passion. You don’t have to find your passion in your first job. Work with smart people. Learn what you can. Your passion may emerge. I had no idea that I would be running a professional association for CFOs and loving it. It just, it, you told me that at 30.

No, I’d be a CFO at 60. I’d be jumping from one startup to another, having fun, always intellectually challenged. It would have been a great career, but I’m just doing something I’m passionate about that I’m excited about and that gets me up every single day.

Anna Talerico (39:34)
That is such a good note to end it on because it’s a through line of all of the interviews I do on careers and finance, which is just, you I think there’s a lot of pressure on the younger generations. They feel like they’re supposed to know what that passion is or find it and don’t do anything but that. But you know, when you stay open and curious and do good work, the passion comes and the paths reveal themselves and they’re often unexpected paths like yours. You so often in this podcast, we’re kind of talking about some of the non-traditional paths into,

but your story really represents where that can take you, know, and something quite different really, even though you’re still serving the finance community in such a different capacity. Yeah.

Jack (40:09)
Mm-mm.

Yeah. I’d add one more, and there’s sort of a story behind it, but your mother and father may have told you this, but just be nice to everybody. And I have a story with that. It’s one of my members, and I can’t name her because she’d kill me. But she got a CFO job for what was one of the hottest companies in her state. She lives in a state where there aren’t a lot of IPOs. There’s not even an IPO a year. She got hired as the CFO

for a company that was on that path and they went public and did great. She has a great relationship with the CEO. She recognized she was like the least experienced candidate that he considered. And when they got comfortable, said, why’d you pick me out of all the more experienced and proven candidates? Because there was a nationwide search. And he said, yeah, she came straight out of one of the big accounting firms. She said, you worked with, do you know Michael Robinson?

And he gave you a good review. She worked with him at EY. Michael was mentally challenged. He grew up next door to the CEO. He put it together. He said, do you know this woman? And he said, yeah, she’s the nicest person in the office. You should hire her. You know, she didn’t get the job just because she was nice. She was a great CFO. But man, that helped, I’m not a big believer in karma or any of those things, but sometimes it pays off. And even if it doesn’t pay off, it’s just nice to be nice.

Anna Talerico (41:32)
Yeah, yeah.

Yeah.

It’s good to be nice, yeah, be nice, I love it. So, Jack, I think CFO Leadership Council people can go to the website, obviously, and see the work that you’re doing and the membership in the community that you’ve created. Secrets of Rockstar CFOs, fantastic podcast. So, highly recommend that, for sure. And just thank you so much for sharing your story and being on the podcast, I really appreciate it. We’re big fans over here, so thank you.

Jack (41:57)
Thank you.

Well, I appreciate the time and hopefully we’ll get to do it again and I’ll have you as a guest on mine.

Anna Talerico (42:12)
I love it, I love it. And I will see you end of October at the Javits Center at the, what’s the name of the event again?

Jack (42:18)
It’s fate, Finance and Accounting Technology Expo. It bums me out that I didn’t come up with the name, because I’m good at that type of thing.

Anna Talerico (42:25)
It’s a good one. All right. Thanks, Jack.