Storytelling in Finance: The Role of the CFO in High-Growth Companies

Welcome back to CFO Weekly, where we're talking with financial leaders about how to build efficiency in their teams, create time for strategy, and ultimately get results with your host Megan Weis. Let's jump right in.

Megan: Today, my guest is Matt Wolf. Matt is the CFO of ChartHop. With a background in finance, Matt's role is to help ChartHop accomplish its company growth goals with predictable transparent metrics and world-class execution. As CFO, Matt spearheads communicating ChartHop's story in a compelling way to investors and the broader market. Before ChartHop, he served as the CFO at Roadster, where he gained experience leading financial services, implementing effective fundraising, and guiding operational improvement. Matt, thank you very much for joining me on today's episode.

Matt: Thank you, Megan. It's great to be here.

Megan: Yes, today we'll be hearing about your journey as a CFO and learning about your current organization, ChartHop. We'll also be discussing topics such as the role of CFO and storytelling, managing high-growth companies, and ensuring their success. I'm really looking forward to learning from you, so let's get started.

Matt: Excellent. Sounds great.

Megan: As always, let's start with you and your journey to how you got to where you are today.

Matt: Sure, happy to do that. I started my career as a lot of CFOs and finance folks do in investment banking, did that for the better part of a decade, then spent some time in some large corporates, abroad mostly. Then I moved into finance leadership at startups around 2015. Most recently prior to coming to ChartHop, I was a CFO of another SaaS company called Roadster, which we had a successful exit there in the middle of 2021. I joined ChartHop as CFO back in January. I've been with the company for about eight, or nine months.

Megan: Just out of curiosity, is ChartHop remote right now? Is everybody working remotely?

Matt: We are, and it's actually been that way since the beginning. We made the decision early on to be a fully remote company. One of the things that we do with the product and also culturally is to cultivate that and get employees engaged when there is no office.

Megan: Yes, that can't be easy. How was it transitioning into the role of CFO remotely?

Matt: I did that at my last company, actually. We went into COVID as an in-office company and learned very quickly how to plan and operate a business from a very decentralized leadership team. I think it's probably not too surprising. What it's going to be, is its constant communication, excellent visibility into an organization, and really coming out of that experience in my last company when I was looking for something new, I found ChartHop and loved the product. It was one of those moments where you say to yourself, "I wish I had this at my last company and every other company I've been working for."

We do at ChartHop, as a people operations analytics platform, really give management and employees a view into an organization, both from an organizational structure perspective, from a compensation perspective, from a DEIB perspective, all those different angles, and just much more visibility than we've had historically. That's what really attracted me to the company. The product itself actually coming on a CFO at ChartHop has made my job a little bit easier, to be honest.

Megan: Who is the ideal client for ChartHop?

Matt: We like to think that any company with people is a good candidate for ChartHop. There is a certain size at which organizational planning/compensation planning becomes more challenging, so really kind of above maybe 100, 150 people is where we start hitting our sweet spot, but we can go into the multiple thousands and beyond. I think when we started out, we were focused, not surprisingly, on small high-growth companies because I think headcount planning there was such a critical piece of operational planning that we found a lot of early traction there. As we've come to see larger organizations are also always looking to optimize, looking to restructure teams to maximize productivity, and the product's really great for that as well.

Megan: Does it sit on top of an ERP, or does it work separately?

Matt: It integrates with a number of different systems. It integrates with payroll, it integrates with HRS, it integrates with equity systems, but it also goes beyond that and integrates with things. We can integrate with operational systems, customer service systems, and sales systems. By bringing in all that data and using the org chart, in some ways, as the visual front end to look at teams, so you can look at things like sales quotas, or you can look at team diversity makeup, and reporting lines, and compensation structure, and where do people fit in different bands. You can look at tenure.

You can look at all these different organizational and demographic metrics and really make more informed decisions about how you structure and operate teams within a company. Really it pulls in data from a number of different systems. It's meant to be an open platform. We want to be able to connect to various systems across organizations, bring all that data in, connect it to the people that are producing and using that data, and give a view into an organization that, as I said, really hasn't existed before.

Megan: Yes, that's really cool. It basically allows you to slice and dice information in ways that you've never been able to before.

Matt: That's right. The other thing that it allows us to do is run scenarios on that information. If we want to look at, for example, headcount planning in a certain team, we look at the org chart and visually add new roles, and then there are obviously tables that exist behind that. With the ability to create scenarios and then look at what that does to your overall cost structure, and what it does to your quota structure, you can basically slice and dice the data in a very engaging and visual way, but one that doesn't give up analytical rigor for that really important UX element.

Megan: You've been with ChartHop now for nine months.

Matt: Yes, that's right.

Megan: Looking back nine months ago, how is it that you were able to hit the ground running?

Matt: I think one of the nice things, it is a SaaS platform, and that's something that I understand, so the economics of the business were fairly straightforward. I think what I was looking for when coming into the company, and I think this is what I always look for is an executive team that engages and looks at finance as a strategic part of the executive team, and was eager to work with me when I came in on budgeting, and planning, and optimizing, and price optimization. In my conversations with the team as I was interviewing with ChartHop, I just got the sense across the board that, one, the team was very aligned, all rowing in the same direction, and was very eager to bring on finance leadership to help continue the journey and work towards the ultimate goals here.

Megan: What have been your proudest achievements since joining?

Matt: I think there are a few actually. Right when I first joined, we acquired a small YC company called Gather. That was within a couple of weeks, and so brought a great team on board and developed that acquisition muscle memory within the company. We pretty quickly put in a very full-fledged budgeting and planning process, and the team was very receptive. I was very pleased that I was able to come in, talk to the team, explain why we were budgeting the way we were doing it, and share the models with them. As I said, they were eager to understand and eager to engage in that.

Ultimately, it was a relatively painless process to put in place even though one really hadn't been there before I joined. I think ultimately, we've continued to grow the company. It's really not been the easiest of environments in the most recent months. I've been just truly impressed with the way the exec team and the overall employee base have responded, has really dug in, and it's a group I feel very proud to be part of.

Megan: Earlier this year, you announced ChartHop's first acquisition. Was that Gather?

Matt: That was. Yes.

Megan: Okay. Can you speak a little bit about what went into that and how the integration is going and advice for successfully integrating?

Matt: Yes, I can talk a little bit about that. As I said, it was a smaller YC company that had a very complementary product that a small and very high-powered team had developed. It was really around actions and automating certain event notifications around people milestones in an organization. They had also built up a really great community of HR professionals that were sharing ideas and they're really facilitating these conversations. A really great team of both on the marketing side in terms of community engagement, a very strong team on the product and engineering side, and was an area of our product that we wanted to continue to enhance, so I think it was just very complimentary when we brought them in.

In terms of advice, acquisitions all have their own flavor, even if you've done a bunch of them either as an advisor or on the inside of a company. I think it's the most important perspective to have to go into an acquisition is that it will look different at the end than what you anticipated it to be at the beginning because all sorts of things come up, sometimes good, sometimes more challenging. It's remaining adaptable and understanding that all these transactions are different and include their own unique challenges around just the entire-- whether it's around structuring, whether it's around technology.

I think we were fortunate to bring in a really great team of people and they were just wonderful to work with. I think that's also really important to have executive alignment, that the objectives are very clear, and that the reasons for doing the deal are very clear to both the acquired company and to people internally really. I think it's something that not all employees go through, especially at a relatively early-stage startup. You want to be communicating and explaining the strategic rationale as to why the deal's being done. From what I've seen, we've brought in some really wonderful people, and it's been a good benefit for us

Megan: We hear a lot today about the role of the CFO as a storyteller. What's the key to being able to tell a company story in a compelling way to investors and the broader market?

Matt: I think that what I've found to be the most helping us that probably will not be the most unique idea, but it really is, and it's something that I enjoy doing, is getting engaged with every team in the company because everyone obviously, as you can imagine, is contributing something to the overall story in the overall progress and growth of the company, whether it's sales or marketing or CX, people ops.

I tend to work very closely with those teams to really understand how they're operating. I don't look at finance as being strictly a budgeting function. I look at it as a much more operational role, a much more strategic role, and I want to have those very frank conversations. I want the leadership of other teams to feel very comfortable talking to me about challenges and opportunities, giving them frameworks to think through how to think about-- whether it's an investment or other decisions, then getting involved in those decisions to the extent that can be helpful.

I think having that granular knowledge of how certain teams operate when you step back and put it all together into a story about who we are, what we're trying to accomplish, and how we're going to accomplish it, you just have the much deeper context to do that.

Megan: That's great advice. ChartHop has plans for rapid growth this year and beyond. What advice do you have for other CFOs who are managing high-growth organizations?

Matt: Again, going back to transactions or just in the overall philosophy around finance leadership is it's just to be adaptable and it's that-- be rigorous in your planning, be hyper-analytical so that when things don't go according to plan, whether above or below, you can understand why they didn't go towards the plan.

Knowing the details around that allows you to adapt one way or the other. Sales are over-planned for a particular reason and everyone's going to celebrate that. Really, why is it happening? Were we too conservative in one of our assumptions? Did something else happen that we hadn't anticipated? I think that the overall-- what I tell my team and what I tell the overall company is let's reduce surprises either to the upside or the downside as much as we possibly can.

In a high-growth company, you just have more surprises because things are just happening faster. You're hiring people faster, your product is changing faster, and your growth rates are just going to be faster. Adding new customers, new customer types, and you're seeing for the first time in a lot of ways how things change when certain variables are altered. I think it's being prepared to deal with that uncertainty in a way that is constructive to the business.

I think when we talk to our teams overall and talk to the company in all hands, I think it's okay to say that we didn't know something was going to happen or we didn't expect it to happen this way, but here's how we're responding to it. It's having the second answer to not say, "Hey, we were surprised and we're still trying to figure it out." That may be the case, but figure it out quickly. I think it's being ready and accepting that things just are not going to pan out the way that you expect them to, and having enough of a granular knowledge and understanding of what you expected to happen to identify and pattern recognize when things don't.

I also think that the other piece is being able to communicate across departments and across teams so that when things are-- even if they're going to plan, why are things happening? Having very frank conversations. I have weekly one-on-ones with all of our VPS and I really do try to understand what they're seeing so they can understand what I'm seeing across the organization.

I see finance really as the funnel point for all of that information that goes into operational performance and being able to communicate and elevate them above their specific teams to say, "Well, this is what we're seeing over in--" If I'm talking to someone on CX, "Well, this is what we're seeing over in marketing," and making sure that everyone is aligned, and again, no one is surprised.

Megan: Yes, I think what you mentioned there, just being able to work across the organization is so important these days. I think that's a big factor in the evolution of the CFO, whereas 20 years ago, maybe you could work in a silo, it's not possible anymore.

Matt: I think that's right. It would make my job impossible actually if I was just creating, spreadsheets in operational plans without really regular input and interaction with people across the company.

Megan: As the company is maturing from startup to something more mature, how is it that you ensure that your processes and technology can scale with the business?

Matt: I think the first thing you have to do is document things. At the beginning when everything is running at light speed, it's easiest to make ad hoc decisions in one-offs, but you find that over time you're making just too many one-off decisions and everyone is coming to you for, "Well, how do you want to do this? How do you want to do that?" I think the earlier you can begin documenting processes and giving people guidance that doesn't have to come from you verbally is infinitely helpful.

Those plans will change over time. Those processes will change over time. Putting them in place as early as possible so people have a reference and can begin to understand the operational cadence. You asked another question as well.

Megan: Process and technology.

Matt: Technology, sorry. You can edit that out. As it regards systems, I think there I'm always looking ahead and it may seem certain systems are really expensive at the time, but looking at it from an ROI perspective and saying, "Look, it's going to cost us X right now or maybe X on an annual basis, but what do we get out of that? Is it error reduction? Is it time savings? Is it more efficient hiring plans?" It really is taking all of that into consideration when thinking about systems, and also eliminating redundancy and increasing integration between systems.

What I also like to avoid is buying point solutions that will need to come out at a certain point in time because something else is going to replace it in a more unified way. It's always looking at, "Will we continue to use this or will we move to something else in, say, a year or two, and does that mean when we replace that one system we'll have to replace three or four, or does something we're buying today continue to be useful into the future?"

I try to be as forward-looking as possible with that, and also, try to see how we can standardize those systems across teams. Every team has its own preferred way of doing things, and every team leader has their own preferred way of doing things. The more we can consolidate and get people working on consistent platforms, I think that sets an operational tone so that when new people come in into the company or move around between teams, they aren't having to learn tools with those moves. You develop expertise that I think can sometimes be underrated.

Megan: Of course, one of the beautiful things about a startup is that entrepreneurial spirit. How do you maintain that spirit while still managing risks?

Matt: It's hard. It's the bottom line because I think you can do things with 10 to 20 people that you can't have 200 people doing, it becomes chaos. One of the nice things about startups and the reason that people come to work for them is that they have an immediate impact. They have the ability to influence how a product or a process gets built or implemented.

Even as we scale to hundreds of people, leadership still has to give their reports some autonomy around how they go about their day-to-day within the confines of a framework of how we're going to operate as an overall organization. Giving product teams enough leeway so that they feel like they're still influencing the product, they're not just being told what to build.

I think giving marketing teams flexibility with a budget so that they are empowered and enabled to go and spend in a way that they best see fit at that time so that they feel like they're able to make decisions, and keeps people engaged. What I think you just don't want to do is when you go from an early startup to a large organization is to have people feel like their roles are being diminished, their voices aren't being heard because ultimately that's why you come to an organization that is moving quickly, it's that you like that environment, you like that atmosphere, and you like the interactions with your colleagues that come with that.

I think it's incumbent on managers to be very focused. Are they asking their teams for things or are they telling them how to do things? I think that it's a fine line to walk because again, there will be more processes, there will be more approvals and things that are needed for certain decisions, but I like to think of it as making sure that people's fingerprints are still on things that they're working on.

Megan: I think people want to feel purpose in what it is that they do.

Matt: Exactly. That's right.

Megan: You may have just answered this, or at least touched on it, but as a financial leader, what's the key to cultivating an environment that ensures employees have the right resources to succeed, particularly in a remote environment?

Matt: I think it goes back to what I was saying earlier about selecting tools and platforms and things. When I come into organizations, I say my job as the CFO is to ensure that everyone has the resources needed to do their jobs effectively, whether that's the right people on teams, whether it's the right software products, or whatever it happens to be.

As we get into a remote environment, that becomes even more challenging because everyone's working in a very different environment, their home. I think you have to be open to listening to people. It's things that work in an office environment. I think we're still-- and we're now three years into this, are getting there and I think we're still finding ways to make that experience better.

We're still finding ways that the existing tools can be used in new ways to increase employee engagement, increase communication, and I also think you need to-- even in a remote environment, you need to ensure that there is still human contact. We do things like all-hands meetings where we bring everyone together. We do smaller regional events. While people are working from home, they have a chance to know someone beyond just a Zoom screen or just a video conference. I think there it's listening to people, understanding how people are efficient in a home environment or a co-working environment versus an office environment where you just have more control over really everything.

There are going to be trade-offs. I think the remote environment may require more meetings because you don't have the opportunity to overhear things and just drop a comment into something you've overheard or just stop by really quickly someone's desk or whatever, but it's being cognizant of that but also respectful people of people's time so that it isn't just meeting after meeting.

It can feel that way sometimes. I think it's important to lay some ground rules as well so that people have-- you asked about resources, but I think their time is ultimately their most valuable resource, so it's giving them the tools, but it's also giving them the space to do their work.

Megan: What are one or maybe two to three of the biggest challenges you and your team are facing this quarter, and what are you guys doing to help solve that challenge?

Matt: That's a good question.

Megan: How's talent? How are you guys finding and retaining top talent?

Matt: That's a good question. I think we've done a remarkable job of bringing talent. I think we offer a lot, just as a company, from a cultural perspective. Working in the HR space, you're very acutely aware of how people feel about an organization. We use our own product internally, so we do everything from one-on-ones to performance reviews to everything using that tool.

We try to keep a really good pulse on our organizational health, the happiness of our employees, and how they're engaged. I think that's always going to be a challenge just because, as I said earlier, you're in a remote environment and you don't see people every day. I think it's really important that you find ways to stay engaged. I think being remote, allows us to find talent in areas that we wouldn't have if we were in office culture. I think that's been a huge benefit.

We found some wonderful folks in markets that we just wouldn't have been in otherwise. I think on the flip side, as the work-from-home environment shifts a little bit, some companies are going back to the office, some are still work-from-home, some are hybrid models, coming out of the last couple of years, and people are going to figure out what works best for them.

Some people like being in an office, some really don't, some like the flexibility, some like the camaraderie that comes about from being in an office, so we're certainly dealing with those challenges, I think all organizations are to some extent just because of where we've been the last couple of years, but I think we do that very effectively.

Part of the way we do that is through our own platform, but then it's also making sure that you're recognizing achievements and rewarding accomplishments in a way that is visible to the organization when you're not in an office. That's how I think we've helped retain some of our best talents because we're not shy about it at our regular all-hands meetings celebrating that.

People want to feel like, to your earlier point, that they have a purpose in an organization. I think it's important to acknowledge and recognize that those purposes are being-- we recognize that as leaders, as an executive team, and as a company. Certainly challenges around talent as every company has, but I think we've navigated that quite successfully in a lot of ways, continued to improve, and we'll continue to look for ways to be better, but I feel wonderful about the people that are at ChartHop. I think we've got just an amazing team. That's where that is.

Megan: ChartHop sounds like an innovative, fun place to work.

Matt: It is. I think we're doing something-- it's interesting when you're building a platform that hasn't really existed before, so you're defining a market niche for the first time. That comes with its own challenges, but also its own rewards when you really can shape the language and shape the philosophy around a new market.

Megan: Lastly, what advice do you have for CFOs who are looking to drive strategic value and make a real impact at their organization?

Matt: I think you have to build relationships across the company in a way that when you need to make decisions as a CFO, and ultimately a lot of decisions do come down to you, you have to be able to, one, take the perspective of other teams into account, work that into your decision process then be able to explain why you made a decision in a certain way. If you can't do that and it just seems like you're making decisions either based on opinion or with incomplete information or even arbitrarily, it's going to start to break down.

I think it all comes down to trust, so you need to have very strong trust relationships between all parts of the company. Without that, you will be operating in a vacuum and it can be a very lonely role. You want to make sure that you have, if not the support, but hopefully the support, but if not the support, at least the understanding of your executive peers as to why decisions are being made, then make those decisions in consultation with your other C-level counterparts.

Megan: That's great advice. Matt, thank you so much for being my guest today.

Matt: Thank you, Megan. This was great. I really appreciate the time. It's a lot of fun. Thank you.

Megan: Yes, I really enjoyed speaking with you and hearing about your experiences and the resulting insights, and I wish you and ChartHop all the best. Sounds like you're both doing some amazing things.

Matt: Thank you so much.

Megan: To all of our listeners, please tune in next week, and until then, take care.