Careers in Finance | Charlie Schilling

Meeyeon (00:00)
Hi everyone and welcome back to another episode of Careers in Finance with CFI, the podcast where we explore the many different paths that people take in their careers in finance.

Today, I am joined by a guest that has had an incredible career spanning across investment banking, management consulting, strategy, and holding senior leadership roles at some of the most influential companies in education and enterprise services. I’m joined today and whoop, I haven’t introduced myself. My name is Meeyeon. I’m a VP of content here at CFI. You’ve heard and seen me here many times before. And today I’m joined by Charlie Schilling, the CEO of Macabacus,

a leading provider of Excel productivity tools for finance professionals. And in this conversation, we’re going to unpack Charlie’s career and what he’s learned from navigating different industries and how he’s leading Macabacus into its next chapter. So let’s dive right in. Now, I usually start off, I usually start off this interview by asking, how did you get your interest in finance? Did you have any influences? But I do know that you did your BA in

Charlie Schilling (00:57)
Thanks for your time.

Meeyeon (01:09)
a very unrelated field. So I’m genuinely curious, how did you get your interest in finance? Was it in school at the very beginning or was it an influence that came later on?

Charlie Schilling (01:23)
Yeah, so I, number one, thanks for having me. I’m delighted to be on today. But as you were saying, I went to Georgetown and got my BA. was a double major in government and history, but spent

a lot of time during college, actually working full time on the Hill, I worked for a United States senator and became fascinated by the intersection of business and government. I graduated from college in 2000, meaning the recruiting season was like the fall of 1999, which was a very hot time in investment banking and on Wall Street. And, so as is the case at many colleges, the banks all showed up in force to recruit

and it seemed like a really compelling way to complement the experience that I had already had in college, working at least part-time on the Hill with some real business experience on Wall Street. And so I went after it was fortunate to start my career at Roberts and Stevens.

Meeyeon (02:28)
And so what was that transition like for you going from academics into the workforce? something that really struck me that I never really thought about before was I interviewed someone named Eric Byun. Eric, hi, if you’re listening. He went from doing his undergrad at Harvard in, my gosh, it’s so bad.

I forgot what the actual stream was, but he did an undergraduate degree in computer science and then went into consulting. And he said, that was actually really nice because I go from working on projects with teams in school to doing kind of like the exact same thing. I’m working in a small team on a project with a deliverable. And so he found that the transition from school and academics into the workforce was a lot smoother

then he maybe could have anticipated if he went into a banking role. You going into a banking role, how was that transition for you?

Charlie Schilling (03:28)
Yeah, I mean, I’m not sure I knew exactly what I was getting into, to be honest. I had the benefit of having two close friends who were in the class above me at Georgetown who had gone to Roberts and Stevens, which is part of my attraction in going there. They were a part of the recruiting team.

So that sort of like increased my confidence going in. But the real reason I think I and others in my class ended up being successful is that it really is a highly structured training environment. And so literally, I remember in July of 2000, there were 100 or so of us ⁓ in that Robertson Stevens Analyst training class who spent like the better part of a month and a half in San Francisco, essentially locked in

a conference room going through like a very programmatic overview of what we would be expected to be doing as junior analysts at that firm. And it really covered all of the major aspects of what an investment banking analyst does. And so it was clear that the firm had put a ton of thought into like the mechanics and the math that we needed to learn in order to succeed, but also the process and really like what it.

Investment Bank does, since many of us were coming from liberal arts backgrounds with really no foundational knowledge of corporate finance, accounting, and the like.

Meeyeon (04:56)
And you stayed in investment banking for, I want to say like four years, was it? Altogether?

Charlie Schilling (05:02)
Yes, it was a wild ride.

So I started in July of 2000, as I mentioned, the tech bubble burst, you know, beginning in 2001. And so there was just lots of dislocation on Wall Street. I was very fortunate in that at Roberts and Stevens, I had begun work, you sort of begin with a general as a generalist, but then, you know, find a slot on a team where you have interest and where they have interest in you. For me, that ended up being in our media and communications.

team based in New York. Our team subsequently then left as a group and we went from Roberts and Stevens to then SG Cowan where we were for several years and then moved again also as a group to Jefferies. And so yeah, that’s sort of how that unfolded.

Meeyeon (05:54)
Does the team move as a group as in like the other bank just hires the whole team?

Charlie Schilling (06:00)
Yeah, mean, primarily driven and this happens very frequently in finance and professional services, meaning law firms, consulting firms, accounting firms and the like

our group head had a long track record of success serving clients in this specific space. And so essentially he was looking for the best platform to help grow our business. And that’s what precipitated these moves.

Meeyeon (06:32)
And during those years, what do you think were a lot? find a lot of people, myself included, I think that first couple of years in investment banking really set me up with the skills and the inner, like not just the technical skills, but interpersonal skills and just general professional polish. I built that up really well there. And I feel like that foundation has really set me up for success for the rest of my career. What were your main

would say learning takeaways, you think, from that chapter of your life?

Charlie Schilling (07:06)
Yeah, I mean, I couldn’t agree more. Like it definitely is a combination of hard and soft skills. I think I definitely had more soft skills going into it than hard skills. So I had a lot of learning to do. As I mentioned, the investment making analyst training program and later my associate training program were extremely beneficial. But I’d say I actually learned the most from the people that I was working for and with and the interest they took in helping me learn how to do new things.

And that was done by setting really high standards for what client work product has to look like, why it’s important. And, you know, that really helped me learn. But I think, you know, one of the things that’s always stuck with me in my career is I remember at one point my boss, was our, or my ultimate boss, who was our group head, he had this saying, which is like, you can come to the meeting even as a very junior professional, but you have to speak. And that was,

What was implicit in that comment was that you had to do the work, right? You actually had to be prepared in order to add value in a way that a CFO or a CEO of a client company would want to benefit from, you know, whatever comment you happen to add in a meeting. And so it was like, I thought it was a, like, it was an encouraging way to encourage people to actually, like, go the extra mile because you knew that then you were going to be

Meeyeon (08:06)
…

Charlie Schilling (08:35)
like part of the group that actually was the advisory team for a client rather than, you know, sitting in some back room doing analysis that was never going to see the light of day.

Meeyeon (08:46)
That’s so unusual and think that’s such a great small piece of encouragement to give any, even like the first year investment banking analyst, that’s such an encouraging thing to tell that person. I’ve actually never heard that before.

But the idea that if you want to attend this meeting, you have to say something that is just like implicitly saying like, okay, you should know what the meeting is about. You’re probably going to be preparing the materials. I think you’re going to have something to say

Charlie Schilling (09:07)
Yeah.

Meeyeon (09:15)
and I have enough confidence in you that I would like you to say something. And that’s a great nugget of him.

Charlie Schilling (09:24)
No, I agree. It’s like it extends. mean, you know, and I think for those that may be viewing the podcast who, you know, have

junior level roles at investment banks or accounting firms, FP&A M&A roles, etc. You know, another thing that’s always stuck with me is it’s like one thing to pull together a piece of information or analysis or even what we called at the time a PIB or a public information book. And that’s sort of like the minimum, right? Like you get the right 10K, the 10Q, the analyst research report, etc, etc, news, whatever. But the next step is actually digesting it yourself and pointing

people to the parts of it that are actually important or they really should know in going to a meeting. And I think that’s the type of thing which is it’s one thing to sort of do what you’re asked. It’s another to then take the next step and actually think about like why the person who asked for it really needs it and take a sort of shot at that. Maybe you’ll be wrong, right? Like maybe they’re actually focused on something else that you didn’t first pick up on, but it shows that you’re actually like thinking a couple steps ahead,

which I remember we were always really encouraged to do.

Meeyeon (10:39)
And out of curiosity, do you keep in touch with any of the folks from that original team to this day?

Charlie Schilling (10:46)
absolutely. It’s a pretty tight group for sure. yeah, both. that team, but I think as importantly, some of the clients that we served at that time, and this is now literally 20 years ago, are still good personal friends.

Meeyeon (11:07)
And around that time, I think it was still the, I don’t know if trend is the right word, but it was commonplace for someone to go to an investment bank or a management consulting firm and then very purposely pursue an MBA and then maybe go back to the firm afterwards. Was that the case for you or tell us how you decided you wanted to go and pursue an MBA next?

Charlie Schilling (11:33)
Yeah. So I was quite fortunate, as I mentioned, you know, our group moved, you know, to across three different firms. And so by the time I decided that I wanted to step off the investment banking train, I guess I was a third-year associate. I’d been doing investment banking at that point for three years, excuse me, for six years total. And I remember it’s. Yeah, it certainly, yeah, certainly was. But I mean, I’ve been learning a lot

Meeyeon (11:54)
And that’s a long time to be doing that.

Charlie Schilling (12:01)
and I was like actually very happy in the role. But I remember by the time I became, I don’t know, a first year associate, then a second year associate, I was spending a lot more time on specific client accounts. And there were specific clients that we did lots of engagements with over many years. And so I got to know some of the management teams quite well. And at some point, a bulb went off in my head that I was just much more interested in the type of work that they were doing

in taking a risk to grow a company rather than the type of work that we were doing in helping them, you know, across whatever the, you know, equity debt or M&A assignments we were working on happened to be. And so I just got really interested in this idea of one day helping to grow a business myself. And that really was for me the impetus to step off the investment banking track, go back to business school, and then eventually pursue a career, you working for and with growth companies

to pursue that agenda. So that was sort of the initial spark.

Meeyeon (13:06)
And for a lot of people, think they go through the phase of, I really enjoyed what I have done since after undergrad. I either want to switch industries altogether, live in a completely different country. And often they use that entire chapter of their life to say, I want to kind of reset with an MBA. And for a lot of our listeners, they might be going through that exact moment in their life. How did you go about picking Tuck? There’s a lot of… 

great schools available to you. What was your thought process when you were going for a

Charlie Schilling (13:38)
Yeah, I thought.

Well, so I knew I wanted to go to a top program because I thought obviously job prospects would be much better coming out of the program. so, you know, applied to the set of competitive schools largely on the East Coast, just because it’s happened to be where I was based and where my family lives that you might expect. Tuck really had great appeal for a few reasons. Number one, it’s a smaller program. And so I felt like I was going to get more exposure.

to faculty but also the community of students and by virtue of being being in a place that was smaller but also a big part of it for me had to do with the geography meaning and

once you’re in Hanover, you are really with your class, right? I mean, literally there were 242 other students in my class and we got to know each other extremely well. And that was really part of the impetus in that when you’re there, you don’t really have that many other distractions pulling you off campus or out of the classroom. And so that ended up for me, it sort of sounds like it’s straight out of the brochure and it actually is because it ends up being a very, very meaningful part of it. But the other aspect to me was that

Meeyeon (14:40)
Yeah.

Charlie Schilling (14:52)
I figured that through my professional career, you know, I had been living in New York City before and it was my intention to return, that I would spend most of my professional life in major business cities and that this was a chance to be out of the city in a place where I could, you know, pursue my passion for the outdoors, which was a great side benefit as well.

Meeyeon (15:20)
And then during your time there, did you have a list of companies that you wanted to do that one? Because at business school, you get that one internship in summer and people typically have a list of like three or four companies where you’re targeting like, this is where I really want to go. Obviously you ended up at a top tier management consulting firm, but as you went through that process, how was the whole journey of applying and interviewing? What was that?

Charlie Schilling (15:49)
Yeah, I really took like a broad view. I remember in my first year at Tuck

and considered almost everything other than finance. So I knew that that was obviously the world that I had just departed and wanted to do something different. And so I looked at general management, looked at consulting, startups were sort of less of a thing then and the big tech companies were not recruiting on campus at that point, although now they’ve turned into like major hirers of MBAs at least over the last five or 10 years or so. But so those are sort of the lanes

general management or consulting and I interviewed across lots and lots of firms. And to be honest, it really just came down to like cultural fit. I happened to meet some members of BCG’s office in New York and really hit it off. thought that the client assignments they were working on were fantastic and super interesting to me based on my background. And it was just, it seemed to me a natural fit.

Meeyeon (16:55)
And then you ultimately ended up going to BCG full time. so now like up to this point in your career, you’ve done investment banking and your management consulting, which are two areas that most business graduates today ultimately want to end up in. Compared to your experience in investment banking, what was the world of consulting like? What were things that you found that the two roles had in common and how did it differ?

Generally, you think from day to day. And also, which one did you end up preferring ultimately?

Charlie Schilling (17:28)
Yeah, good question. So I think, so you’re right, so I did my summer at BCG and then started there full time after graduating from business school. I think there are lots of similarities in the roles, meaning like you need to have, or at least have the ability to learn the technical aspects of the job

and how to build a model, how to properly put together a narrative in a deck that can help persuade a group of people to do something or at least become more aware of an issue so they can make a choice. so like lots of the nuts and bolts are the same. But what I would say is that the set of business problems that you’re working on is just totally different. Right, the assignments that I took on at BCG were totally different than the types of

assignments that I was working on in investment banking. I’ll give you like two examples. So while I was a banker, we did a lot of where we helped a lot of clients buy or sell companies.

But in the M&A context, that’s like all valuation-based, leading to obviously the price a company should pay for another company, or whatever price happens to be agreeable on the sale. At BCG, I also worked on M&A, but in a very different construct. I remember one specific instance, we helped Capital One buy a bank, which was called Chevy Chase Bank, in the Washington, D.C. area.

There was all around the post-merger integration planning. And so the actual people parts of the business, the systems parts of the business that really we would never touch or in large part never really consider as part of the pure investment banking advice that we were giving. And so it was just sort of a different dimension of the same set of problems in a way, which helped me, I think, understand the world of business in a different and perhaps richer way.

Meeyeon (19:34)
I think that reminds me of a point that Tim brought up, who is CEO of CFI, with the investment banking side. was like, I enjoyed being on the advisory part where we were either advising businesses on purchasing or investing something. But being at an operating company, maybe a similar to the management consulting side, where you see the after effects of that decision and you get to help

put those things together and sort of like just live with that decision, so to speak.

Charlie Schilling (20:06)
Yeah, totally. And it really helped me appreciate the additional dimensions that exist even just on one transaction.

Meeyeon (20:15)
And so after you’ve done those two roles, which one did you prefer? Like if you were to say today for whatever reason, let’s say you were going back to BCG or to an investment bank, which one do you think you would prefer today?

Charlie Schilling (20:29)
It’s a very hard question for me to answer because I think they, for me personally, they exist best in combination. But I think I was a better…

member of the BCG team based on my experience in investment banking. So it’s hard for me to make a choice between one. That said, know, I’m well, relationships have just been important in both instances, right? So the people that I worked with in investment banking have become lifelong friends, but same thing at BCG. And in fact, in several instances, I’ve gone back to the firm and hired them for advice on specific assignments. So it’s created sort of a tight-knit web.

I know that’s not an answer to your question.

Meeyeon (21:12)
And then so after BCG, you went to Bloomberg. How did that transition happen? Were you scouted by the company by like a recruiter or did you, were they maybe a client of BCG?

Charlie Schilling (21:23)
Yeah.

No, exactly the latter. I had been, so I went to BCG full-time. I’d worked on, well, guess I worked on

two or three financial services cases, but then got staffed on a Bloomberg project with two partners that I really, really liked at BCG in New York. And we did, I think it was like two or three projects in succession for Bloomberg. And so I got to know the team there very well. This would have been, I guess, 2009

time frame. Bloomberg at that point had a relatively new president and then CEO whose name is Dan Doctroff who was building a team in what was then called the CEO’s office which was broadly responsible for strategy and M&A and they were looking for people that had investment banking and or consulting backgrounds and to come play roles on that team and so I got a call from what at that point was an existing client to come do that full time and I

at the chance. It was far earlier than I would have anticipated ever leaving BCG. I think I left as actually just a second-year consultant, so my tenure at BCG was not all that long. But in many ways it was a dream job because it was a chance to step into the operating environment in financial services or information services, which is a world that I knew at least something about and had massive and continue to have massive respect for the brand. But importantly, it also linked back

to my interests in college and in government more generally, in that obviously Mike Bloomberg has really moved the needle on the issues that he cares about, including through the company and so it was a place that I was like thrilled to go work.

Meeyeon (23:15)
So up to this point, would you say that, so in, found personally that investment banking roles, was a lot of like individual contributor type work and everybody worked really well together, but we were typically kind of working on our own pieces that would all get merged into a pitch deck. And then as you go through the, the, the ladder, so to speak, you become, you get more leadership and more managerial type of roles, but you’re ultimately managing like

the best individual contributors. So I never got to really learn as much or lean into just an experience of developing leadership skills in that environment. Today, you are the ultimate leader. You’re a C-suite leader. When did you start, you think, really developing your leadership skills? Was it when you went from BCG to Bloomberg?

Charlie Schilling (24:08)
That’s a good question. So I think I had…

Well, I think it goes back even further than investment banking for me in that, you know, I’ve always been parts of groups where, you know, I was able to either observe or be a leader. Sports teams come to mind. So I sort of had developed an appreciation for what being a good leader looked like. And then I saw it in action while I was a banker. I mean, I hold our group head, who I worked for and others on that team in extremely high regard, same thing at BCG. And so I feel like I saw really

good examples of what leading in super intense work environments can look like that definitely informed my approach. But even through my time at Bloomberg, I was largely in an individual contributor or small team leadership role. I wasn’t actually in a position where I was calling the shots myself. And that actually was in part the influence for me to leave Bloomberg

and pursue what has since then been a series of much earlier stage growth oriented company roles where I would have the chance to make even more of an impact and combine what I think is a certain level of financial acumen plus strategic thinking ability, commercial drive, plus leadership skills in order to help grow pieces of businesses and now a whole company. And so I really think I’ve learned it 

along the way, but learned it by watching and by testing what works. At the heart of it, I think I’ve always been a very people-oriented person, able to kind of put myself in the shoes of another and figure out what might motivate person A versus person B, knowing that those two things can be very, very different, and then figure out a way to build teams that can get the job done and imagine something new.

That’s sort of been learned along the way.

Meeyeon (26:18)
And so from Bloomberg to where we are today with you being the leader of Macabacus there’s a couple of chapters that happen in between. I’d love for you to take us through the moments in between there and maybe share with us some kind of like key highlights, lessons learned during that chapter because I find that more and more people are becoming interested in careers outside of the traditional path in finance.

I think that personally coming from a business program, I often see people going through the, know, I want, have to be an investment banking analyst or I have to be a management consultant. And there’s, that’s a very small hole for people to go through. But now that like we have things like CFI where we’re educating people about different areas in finance, I find more and more people are also interested in trying to help small businesses grow, being part of a, maybe not necessarily seed stage.

But a smaller company is really learning how to grow that company and becoming an expert in finance in a very different way. So I think that ⁓ the time between Bloomberg to now would be an amazing insight for our listeners to have.

Charlie Schilling (27:31)
Yeah, so I think, so the big jump was, and by the way, it was like somewhat opportunistic, meaning when I was at Bloomberg, I wasn’t necessarily looking for my next role, but I happened to get a call.

from a company called GLG, which is a player in the expert network space, which may be familiar to people listening to the podcast. That was a service that I had used as a client while I was at BCG, but also at Bloomberg. And so I was very familiar with the product itself and hugely enthusiastic about it. They were beginning to build a new business within GLG and needed a leader

for that business that was really going to play the general management role, meaning commercial service delivery, product marketing and the rest. And so that was a great opportunity for, in my mind, to take a step up in my career and move out of an advisory capacity into one where I was actually helping to grow a business responsible for P &L, leading people. And so really was like the fulfillment in a way of the journey that I had started by

leaving investment in the first place. So that was kind of the turning of the page or flipping of the chapter, if you will, that got me into that like first P &L slash leadership role. We had some great success in doing that. It’s a great product. It was a great product then, is now. And I found that really energizing. It was my first foray, if you will, into the commercial environment where I was actually responsible for a team that was selling something directly

versus being part of that team and I really enjoyed it. I knew I wanted to do more of it.

Again, very opportunistically, I got a call from a company called General Assembly, coincidentally, had been started by a classmate of mine at BCG. They had what at the time was a large, fast growing consumer business, but wanted to build a business with a similar set of products to serve the B2B market, which is a place where obviously at that point I had some expertise. And so I jumped at the

chance. It was an earlier-stage company. This was 2016, so I guess the company at that point was four years old, but it was a very, very interesting time in the New York City tech ecosystem and General Assembly was a great player there. So I jumped at that chance, had a good run there. We ended up selling that business in 2018 and about a year and a half later I was sort of looking for my next thing. Jumped to another education company, the Foss.

following year, very similar role, but I think on a bigger platform, which was, I thought, a logical step in my career. But I was still, at that point, the general manager of a business unit rather than the company as a whole. And I was fortunate earlier this year to be asked to take the role of CEO of Macabacus, which is where I am now. And I’m very enthusiastic about what we have in front of us to help our clients to their jobs better and help in that regard.

Meeyeon (30:51)
Do you find, so it’s really interesting because when I had my conversation with Tim, we talked about moving from roles that were very analytical. So investment banking, very ⁓ analytical. And then perhaps in being towards more operating companies and having for Tim, as well as myself, having the fear because people were telling us at that point, okay, like if you’re going to move from an analytical role and you start to move away from that, it’s very difficult.

for you to ever make your way back towards that again. And for me personally, I remember, and I still kind of go through this, where I started at BMO and their investment bank and my career has taken several twists and turns since then. But I still see every once in a while, a couple of my friends that started there that are still there, been there for so many years at this point and are managing director or heads of groups. When you change roles, a new opportunity finds you. Do you ever…

have any moments of hesitation? Do you have any moments of regret? Because I get the sense that new opportunities come your way and you don’t hesitate. You think, this is exciting. I’m really interested to work in this type of area. And then you go for it. But for those of us listening that are navigating those changes, would you just, I would love to hear from you your perspective.

Charlie Schilling (32:16)
Yeah, I guess it goes back to someone’s risk tolerance. In that, guess mine has always been sort of high and I’ve just always really admired people that take risks, help grow companies and at the end of the day, employ more people who are able to contribute in meaningful ways to their own families, communities, you know, et cetera. So that’s kind of always been the drive for me, but that’s a personal one. And it sort of…

drew me towards the types of opportunities that I pursued over now the last quarter century, which pains me. It pains me to say I’m actually getting pretty old. But look, I think back to what you were talking about earlier, I think there are great ways for people with strong analytical backgrounds to make the jump into the corporate operating environment and add a ton of value in ways that are outside of corporate finance…

Meeyeon (32:54)
Ha.

Charlie Schilling (33:14)
or FP&A like as lanes. I mean some of my most valued partners over the years have been people that play CFO roles and are really thinking about the business from like an operational and financial perspective. It’s super super important and like directly linked to the strategy of an overall company. And so I think there are really really interesting roles that people can pursue in finance for sure. I mean I’ve got lots of friends who really did

stick at it, right? Like started as investment banking analysts right out of college and are still at it just as you said moments ago, like either as group heads or running parts of large financial institutions and they’ve had great rides. But I think in some ways the journeys become parallel and that as you ascend to senior leadership positions in those firms, your job becomes not just about the technical work product that you’re pursuing, that you’re able to produce, but instead about your own commercial ability, your ability to be

strategic thinker lead a team to do something new that helps the overall firm grow. And so in a sense I think those worlds converge and though you know sort of doing it at different stages and perhaps in a different a different sequence.

Meeyeon (34:30)
And then I know that a lot of our listeners aspire to eventually become leaders, whether it’s CEO or CFO at companies one day, whether they found them or join large corporations. I’d love to get your take on leadership. What do you think is, how would you describe your leadership approach when it comes to like scaling businesses and managing change?

Charlie Schilling (34:57)
It’s a good question and I definitely say ⁓ it’s a work in progress because every situation is different. But I can tell you what I aspire to be as a leader, which is ⁓ really to be ⁓ a servant leader. I’m a big believer in that construct, which is that my job is to make every single person on my team as successful as they possibly can be and orient all of the capabilities that we have across the company in order

to help make that happen. That gets complex pretty quickly because you’ve got to have the right product in the right market with the right commercial team in order for the business to actually make sense from an economic standpoint. But I really sort of view that as my job. And so the way that I go about that is first by listening and trying to figure out exactly what our clients need, what we can build, what the capabilities of the team might be in order to help pursue that agenda

people behind that effort. think I’m a big believer in sharing information, collecting feedback from across the various quarters of a company and then synthesizing it into a way that makes sense. And I think that leads to a really important piece of this which is the ability to communicate and then repeat that same message in a way that is not like repetitive but instead make sure that you are reinforcing the right points so that people understand not just what you’re asking them to do but why

you believe it’s so important. And I found over time, even for myself, when I played more junior roles, that that’s really empowering, right? It’s one thing to be asked to do a specific piece of analysis and do it well, but it’s a whole different thing if you understand why it’s important and critically, like what the person that just asks you to do it is gonna be doing while you’re off doing that piece of analysis such that the whole thing will come together in a way that really does feel like a team. And so those are, think, some of the elements that

try to think about as I function and grow as a leader myself.

Meeyeon (37:03)
And

from all of your career and I would say a mix of professional and personal experience so far, because we don’t just grow as professionals. Everyone grows in so many different ways every day. Was there a piece of advice that you would give to someone that ultimately wants to end up in a leadership role, like a CEO one day? That someone is, you know, like chipping away at being an investment banking associate. And ultimately they say, you know, like 15 years down the line,

really want to be a CEO of a company. Is there any general advice that you might give them to pave that path towards leadership?

Charlie Schilling (37:41)
Yeah, definitely and I’d say it’s like if you decided that you want to make the leap towards

general management in some capacity someday. Having started in either like a finance or strategy role, I think it’s pretty important to pick a lane or a discipline that you know you want to get really good at. And there are many, right? Commercial or sales is one. And for me personally, that was like the drive, but it could equally be product or like several others. So that you really are known for a well-developed set of skills in a specific area that

can add value to a company in the long run. And actually, as I look back on my own career, it’s something that once I had made the leap out of consulting into the operating environment at Bloomberg, I wish I had asked for that type of responsibility sooner. In that, like that track from being a successful salesperson, sales executive, CRO is often like a great path to other C-level roles within a company because you really are the closest to the customer and therefore can

lots of things within a different firm. So I think that’s the piece of advice which is think about like based on your own interests, your own personality, which of those lanes really sparks your interest and build experience in that area.

Meeyeon (39:05)
And then now we’re going switch gears because I want to, this is always a fun part, rapid fire question to get to know you better as Charlie the person rather than the CEO of Macabacus. So these are kind of like all over the place. What is a favorite book that you’ve read recently that you recommend people read, whether it’s just for personal interest or something work-related? Book or podcast?

Charlie Schilling (39:31)
I just read Graydon Carter’s book, which I thought was…

Very interesting. So Graydon Carter, former editor of Vanity Fair. And it’s the book that comes to head because I literally just read it last week on vacation. A quick read for sure, but it’s a fascinating tale about like all the glitz and glamour of the New York media scene through the 90s and 2000s. A really fascinating, interesting read.

Meeyeon (40:03)
And what is your favorite band? Band or musician?

Charlie Schilling (40:07)
Favorite band? I’ll go with the Warren Trugs, which is an amazing rock band based out of Philadelphia. The drummer in that band was several years ahead of me growing up, but I know him a little bit and I’ve always hugely admired what they do, highly recommend.

Meeyeon (40:29)
And then something kind of macabre related here. What is the spreadsheet shortcut that you can’t live without?

Charlie Schilling (40:37)
Oh my God. There are so many. I’ve got a list of 150 that Macabacus can teach you. Literally, I’m gonna answer that question a different way, which is like early in my career, this ability of getting off the mouse and using literally just the keyboard saved like probably months of work. And so I’m a huge believer in the shortcut.

Yeah, anyway, that’s my response. Get off the mouse as quickly as you can.

Meeyeon (41:08)
And then let’s see, this one is not as rapid fire, because it’s a little bit of a different question, but what’s one mistake that you think you’ve made that taught you something really big?

Charlie Schilling (41:22)
That is a great question. I’d say one is

you know, and this has happened, I’m thinking of an instance a few years ago where in a somewhat frothy fundraising environment, I was asked to build a team

and given the resources to do it without perhaps properly thinking through all of the strategic implications about like what that meant, meaning we were probably too far ahead of the ball. And that mistake meant that we hired a bunch of people that, unfortunately, we later had to lay off, or we had to lay off a good portion of them. And so I think, you know, as you progress in your career, the impact of the decisions that you make go beyond obviously just yourself and your immediate team

really are affecting others. And so I think it’s always it’s been a cautionary tale for me in that you’ve got to get like you’ve got to just build super levels of conviction around what you’re being asked to do. And just because someone asks you to do it and gives you the resources doesn’t necessarily mean it’s the right call. You’ve got to have the courage of your own conviction in order to go down a road. And I think that’s been an important lesson for me to learn.

Meeyeon (42:45)
And then I think this one’s a great one to close us out on. What is one thing that you wish someone had told you at the start of your

Charlie Schilling (42:56)
Don’t worry so much. I think that people often have the ability to kind of perseverate and overthink things versus like trusting the process in a way, doing the work and like seeing how things will actually play out. And there have been parts of my career where, as I’ve gone from step to step, I perhaps overthought things and, you know, I’ve had to develop some of the confidence that I think I now have today.

Meeyeon (43:32)
That is a wrap for this episode of Careers in Finance, then, and a huge thank you to Charlie for sharing his incredible journey thus far with us, from Wall Street to leading fast growth teams across global education and now shaping the future of finance tools with Macabacus. If you, who are listening, would like to learn more about Macabacus, you can, of course, visit macabacus.com or follow Charlie on LinkedIn as well.

If you’ve enjoyed listening to today’s episode, don’t forget to subscribe, leave us a review, and check out the conversations with other finance leaders across various industries for us. Thank you for listening, and we’ll see you next time.

Charlie Schilling (44:11)
Thanks for having me.