In this episode, Scarlett O’Sullivan, CFO of Leaf Home, joins Jack McCullough to discuss her journey from investment banking to becoming a leading CFO in the home improvement industry. O’Sullivan shares insights into her role at Leaf Home, strategies for navigating volatile markets and the importance of strong leadership and innovation in driving company growth. Listen in as they explore the challenges and rewards of scaling a high-growth company and the vital relationships that support successful financial leadership.
—
Listen to the podcast here
Introduction To Scarlett O’Sullivan And Leaf Home
We have a great CFO whom I’ve been looking forward to having as my guest for quite some time. Her name is Scarlett O’Sullivan. She’s the CFO of Leaf Home. Scarlett, welcome to the show.
Jack, thank you so much for having me. I’m excited to be here.
I’ve followed your career for a little bit since your first CFO job, which we’ll get into. Leaf Home is an exciting company. You guys are doing some great things, but not yet a household name. Can you tell our audience the 10,000-foot view of what Leaf Home is all about?
Leaf Home is a leading direct-to-consumer home improvement company in North America. We’ve been around since 2005. We originally started in gutter installation and protection. Since then, we’ve added a number of other products, such as water filtration, bathroom conversion, stair lifts and garage flooring. We have 200 locations throughout the United States. We’re able to cover about 85 percent of U.S. zip codes. It’s a bit of scale. We’ve gathered about 1.5 million customers in North America.
Before we get to Leaf Home, I want to talk about your own background. Where’d you grow up, Scarlett?
It’s a complicated story. I’m originally from France. I was an expat child growing up. I grew up throughout South America and Europe. I ended up back in France for my last several years of high school before coming to the U.S. for college.
You went to high school in France?
Partly in Paris and Madrid.
Your background might be different than some of the other guests we’ve had, but what was your first job of any sort? Not your first professional job, but maybe as a teenager or a college student.
It was in high school. This is going to sound incredibly cliché, but I was a math tutor. I had an inkling toward numbers. I enjoyed numbers and helped out by teaching geometry.
Mine was Burger King. You went to Yale and Wharton for undergrad and grad school. I want to talk about that. You couldn’t get into any good schools? Your parents must have been devastated that you ended up with a couple of safety schools.
It’s interesting that you should say that because I had never lived in the U.S., I was excited to come over here. It was one of the things my parents instilled in me growing up. Going to America was a dream, something they had wished they had done as kids. I went to American schools even though I lived in all these different countries and always hoped to get to the U.S. I was lucky to get into Yale. It was a bit of a culture shock, as you can imagine, coming from overseas. It was a great experience. I ended up at Wharton, which I did while working as an executive MBA and a banker.
I read an article, it was funny, that listed the most famous fictional graduate of all the schools. Do you know who it might have been for Yale?
I don’t know.
It was Thurston Howell III from Gilligan’s Island.
I didn’t grow up on Gilligan’s Island, so I’m missing a little bit of that subtlety there.
You didn’t get to appreciate the genius of Sherwood Schwartz until you were an adult, or maybe when your children were kids, but The Brady Bunch survived for generations. MIT had a lot of them. I forget the Iron Man, his true identity. He was deemed the most famous fictional MIT graduate, along with Howell III.
I want to chat about your career journey. You mentioned you were at Wharton and got an executive MBA along the way, but you started out in investment banking. You worked at Robbie Stephens, as we called it, perhaps people who worked there did not, and Morgan Stanley. What was that experience like?
Morgan Stanley was the first. I started there right out of school. I went into equity capital markets. I had no idea what I was getting myself into. People were talking about investment banking, and there was heavy recruiting on campus. A lot of the economics majors gravitated toward it. I had no idea what it meant, but I wanted to experience it.
I was in New York and started there. I felt I might miss out on corporate finance, so I requested a move in my second year. I had a chance to experience a bit more of what I thought investment banking was supposed to be like. I covered the aerospace and defense space as my first industry conglomerate. I wasn’t sure if it was for me, but I wanted to see the size of the business.
Robertson Stephens was something that came up. I got a call. I had an inkling about technology and was always curious about what it would be like to be in California. I decided, “Let me see what investment banking is like at a different place, a much smaller place.” I found out that I liked it. I ended up staying for several years and covering a number of different technology spaces with Robbie Stephens in San Francisco, New York and London.
I’m grateful for those years. It was incredible training. I’m quantitative and analytical, so that was great training to be able to gather those skills. It was a good way to start. At first, I wasn’t sure, but I found out that I liked it. I loved working with management teams, crafting stories and taking companies public, which is mostly what I did.
You also spent several years at SoftBank in a different role. What was that like? Were you a partner at SoftBank?
I ended up in London. I took a break, Jack. I ended up taking several years off. If you had told me earlier in my life that I would do that, I never would’ve guessed I would, but I ended up in Tokyo as a trailing spouse. While I was there, I was itching to get back into my career. I was quite certain I didn’t want to go back to banking, but I had always been curious about what it would be like as an investor.
I ended up joining a fund that was sponsored by SoftBank. That was based out of Hong Kong. I was based in Tokyo. I got a chance to go to headquarters in Tokyo from time to time at SoftBank. I brought the job back with me to New York when my husband moved back to the U.S. I quite enjoyed moving from transactional banking deals to investments and spending more time looking for investments, but I also had a chance to monitor, continue and understand what the businesses were doing to see how they would get to their goals.
That was a good transition. The dynamic of being in a remote office with headquarters in Japan was something to be navigated since they were such an important investor of ours. It was an amazing experience, and I’m grateful to have had the experience in both the early and late stages of investing with SoftBank.
Transition To Rent The Runway
You had a great run, and you became a CFO at Rent The Runway. It is happening more, but it’s still unusual for somebody to go from that world directly to a CFO type of role. Do you think it’s a good and viable career path? Do you think you’re a little bit of an outlier for somebody who aspires to become a CFO?
It was several years ago when I joined and became a CFO at Rent the Runway. It was unusual back then. It feels like we’re seeing more of that now, whether it’s bankers or investors moving towards operator roles. I remember the board having a bit of pause on that. Did it make sense to have someone who had never been inside of a company help navigate the next stage of the company’s growth? There was a lot of transformation ahead of us. I feel fortunate that it happened, and they took a chance on that transition. I do think it was more unusual then.
Having said that, I wore several hats, and I still wear them. I do think the banking hat, which is about strategy and thinking, “Is this something that could become a public company, or something that might be an acquisition or an acquirer at the same time.” And the investor hat in mind for that investor constituent.
Those hats were hats that I wore all the time when I was at Rent the Runway. I wear them here. Even though it is unusual, it has helped me in my role. I constantly use those perspectives as I think about where we are as a business now and where we want to be in the future. It’s a way for CFOs and aspiring CFOs to think that there’s no direct path. You can get there in different ways. I’m proof of that. I enjoy the role. You see me doing it a second time at a different company.
I’m a boomer. I became a CFO through public accounting. Without any statistical analysis, I would say that if you were to ask CFOs who are approximately my age where they started their careers, I would bet 80 percent to 90 percent of them started out in public accounting. In the day, it did seem like a good path to get there. Get the basics of finance and accounting. Take a controller-type job. Get promoted to the CFO or find one. You develop your skills. You mentioned you never worked inside the company, but the CFO role is externally looking and externally focused these days. It does seem like people with the background you had would make sense.
I didn’t have that accounting background. My understanding with our board at the time was my first hire had to be a strong controller. I needed to feel that side of the house was well covered. It doesn’t mean that you step away. You have to understand what’s happening. You have to be there to guide and mentor. I needed to know there was an expert in that area who had been brought up to deal with those issues. That was something I wanted to make sure I understood at the beginning, and it continues to be how I operate here.
You weren’t brought in because they saw the potential to close the monthly financial status standard. They had other aspirations. You joined Rent the Runway. It was your first CFO-type job. You were brought in with the idea that you could execute an exit, be it an IPO, or get acquired by somebody. Is that a fair assumption on my part?
That was at the back of the board or the management team’s mind as one of the factors. I vividly recall one of my interviews with the CEO. I’m someone who likes to be in the weeds. I’m someone who likes to understand how the business works and get deep, which doesn’t mean that you don’t still elevate. You have to be strategic. She was looking for a partner. She was looking for someone who could not only be the finance partner but be the partner in the journey of the business. We understood each other early on in terms of the questions, the interaction and the vision. I wanted to understand the vision, the strategies and the questioning. That comes from the banking and investing background.
Part of it is the willingness to jump in. From my side, finance had not been at the table. I didn’t even report to the CEO at that time. For me, it was also a way to bring finance into the equation because I’d never been a CFO before. Most of how I thought about the role was having observed many CFOs over time through my banking experience. You work on an IPO. You spend several months with a management team, particularly the CEO, the CFO and sometimes the COO. You get to see what some great traits are and what some traits aren’t as good. I picked and chose the pieces that I thought were most interesting to create my CFO role, and I learned and adapted along the way.
Tell me about the team that you had at Rent the Runway. You went through a successful IPO, but sometimes, the team that gets you there doesn’t have the skills to lead you after the transaction. You need to change up the early people. There’s nothing wrong with either group. In early finance and accounting, smaller companies require different skill sets and an entrepreneurial mindset. You’re focusing on the transaction and the life after the transaction. It can be different people. How did you work with your team when you were brought in with this vision?
When I joined the company, they had already been around for several years. There had already been a crew of people who had been there from the foundation of the company as they were developing the concept. Rent The Runway was interesting because it disrupted a massive space and the way women got dressed. For the first time, you didn’t buy clothes anymore, you were going to be renting clothes. There was a lot to be done around thinking about what the idea was and educating the consumers, the brand and the market.
You had people who were extremely passionate about the mission and what we were trying to do and who were scrappy. That was one of our core values. Scrappiness is a virtue. Scrappiness is great, but you get to a certain point in time—I was part of it, or along the timeframe that I came in—the company was looking for the next level of professionalization and scaling. That happens with the people.

As I came in, we switched out the controller and brought in someone who had some public company experience. The company didn’t go public for another few years. Over time, we were continually adding skills and preparing because you don’t prep in a few months. You have been preparing for many years to get to a point where you can go public.
We were balancing, advancing, growing the team and adding functions. We didn’t have tax in-house. We decided, “We’re getting big enough. We want to be able to bring that in-house.” We grew the team because we wanted to have specific partners for all the business areas. Over time, you scale and grow. As we got closer, we added more functions. We were beefing up our control people, the IT and the finance side of the house, adding internal audit and investor relations. You do it along the way.
Someone told me something that stuck with me, which is if you think about a company growing and if the company is tripling in size, you almost need the leaders and the managers to also be tripling themselves in terms of their impact. When you think of it that way, it’s a big expectation. We did have to, at different points in time, change out the team and have different people. Some people prefer the early days. Some people prefer a scrappy approach, which is productive and can get you quite far. There are times when you need to systematize and professionalize more. We went through that scaling at a few different points in time.
I was one of those CFOs. I was good from 0 to 65 to get you on the highway, but if you had aspirations of taking the company public, you needed to go faster than 65 miles an hour. Maybe I could have done it or couldn’t have. I don’t know, but I do know that there are a lot of people who could do it better than I could.
Lessons Learned From Going Public
I had my niche that gave me a fulfilling career. I liked what I did, but I handed it off to somebody like you when the time was appropriate. It’s a good model, but what are some of the key learnings that you can share with our audience about preparing for and going public? A lot of the readers are with venture-backed, PE-backed startups, and visions of IPOs dance in their heads.
There are many different learnings and many things to think about. Number one, it is a journey. You can put on a piece of paper when you start the process and when you think you’re going public. That could look like several months, depending on where you are. The reality is there is a lot of work that has to happen ahead of that. It’s not inexpensive work.
There’s a bunch of work on the finance side to automate, to bring on robust systems and to upgrade your ERP potentially. That ties to your technology. There’s a bunch of work around controls. There’s a lot of prepping along the way that has to happen. It’s a balance because some of that prepping can be quite expensive. You might start and realize, “We’re not quite ready.” You might stop and start again later. First, it takes a long amount of time to be able to do that.
In terms of the story itself and going public, there are a few things I would say. One is that the predictability and the performance of the business are critical. I can’t imagine being able to try to guide the street and guide analysts on how you’re going to perform if you don’t have some confidence in the predictability of the business. There always will be something that happens. You have to have enough of a way to figure out how to deal with that because there will be another external element or something that will show up.
The predictability of performance and the story you’re trying to tell are important. Do you have all the pieces of the story to tell it? We tested the waters. The ability to go in front of investors before you’re even going or before it even is an investment for them. Before that, we had crossover investors on our own cap table. We could have a public lens and sense of what they were looking for, both in terms of expectations. It could be around KPIs or business performance.
There are many parts of the storytelling that you have to feel good about. You have had a chance to test it, get some feedback and incorporate some of that feedback. You also find that you tell people things, and you want to be able to come back and deliver on those things. It’s about the performance of business operations.
Those are some of the things that I would say are important. It’s having the right team. It’s not a moment in time. It’s not about getting there. There’s everything that happens after that, and it’s important to make sure that you have a team because as the CFO in particular, you are the most involved, if not the most involved. To know that you have a team who’s back at the house, continues to run the day-to-day, and continues to drive that performance is important because you’re going to be spending all your time in meetings with bankers or research analysts or drafting the one of the business. A lot of preparation has to go into it, and remembering that it continues beyond that.
I don’t know many successful CFOs that don’t have a completely trusted second in command, whether it be a VP of finance controller, chief accounting officer, or somebody they know can, without question, make the trains run on time. It sounds like you had that there.
It’s a group of people. It takes a few people.
Somebody once described to me that an IPO is a financial transaction. Other than the formation of the company, it’s the biggest transaction in a company’s history, but it’s a cultural event because you go, and one day, you have this cool entrepreneurial company. The next day, you have to behave like a publicly traded company. It’s not truly one day or another, but how does it change a company’s culture for better or worse?
There’s a lot of anticipation. Managing the communication around it is something that you want to do carefully. You don’t want to get people too excited about it early because you never know what might happen, whether it’s the markets or something else. There’s a core group of people who know. People get excited because they are proud. At Rent the Runway, it is a business that’s done a tremendous job hiring people who are passionate about that mission because it was a mission that was disruptive and difficult to do and convey.
It took a lot of storytelling. Getting to the other side made everyone feel proud of all the work that had been done over many years to get to that point. The reality is that the day-to-day doesn’t change. If you were driving accountability before, you’re still driving accountability. It’s just much more visible. One of the things that changed was the transparency, especially in how you managed communication with employees. There’s a lot more transparency after earnings are reported than you would’ve had before. People have a much easier way of telling how their work has impacted the performance of the business.
From a cultural standpoint, the culture is there to start with. What people believe in, what brings them all together and what drives them doesn’t change. It’s that you have more visibility both in the public markets and in terms of the performance of the business. Sometimes, that can be disruptive. The stock will move in a way that is not understandable. People don’t quite understand that. Culturally, it wasn’t such a big change, at least from my perspective, because the culture was strong.
Transition To Leaf Home
I’d love to chat with you about Leaf Home. You had a great run there. You’re at what seems like another high-potential company. This will be the dumbest question I’m going to ask during this conversation. What attracted you to the role at Leaf Home?
I took a break after I left Rent the Runway. It took me time to figure out what I wanted to do. In the end, I ended up chatting with this company for several months from the first conversation. I joined for a few different reasons. One, I like to learn. I will continue to be a learner at heart and want to continue to develop and grow. I was excited about the fact that it was a different industry, and I would get to have to learn all over again.
I’m excited about the space that the company plays in. It’s a large market. There’s a large market opportunity. We’re early on in gaining market share. At the same time, the company has scaled quite a lot. The company scale was a testament to its competitive advantage. The fact that it’s able to win and its products resonate with customers. Sometimes, you have a large market, but the products don’t quite match. The scale was a bit of that testament.
The combination of an exciting market and the mission is important. I’ve mentioned the mission twice. It’s one of the things that motivates me. People care a lot about their homes. We’re trying to help homeowners manage their homes and simplify home ownership for them by providing these great home improvement products. That resonated with me.
I think about where it is now and what the future is. What are the growth opportunities here? There are a few different axes of growth and future prospects for the business. As a finance person, it’s the financial track record. Strong growth and profitability were important. We’re there. The important thing is the people. Part of the reason why it took me several months is I spent some time getting to know the people and investors and trying to understand the culture. It’s all those things.
It’s not that different than the type of analysis that you do as an investor. As you look for another investment as a venture capitalist, it’s a similar type of checklist approach that I used before. I spent more time on the people side. It’s the people side because of the Rent the Runway experience. I realized that the people are what make the experience. Having great people around you, great people you can rely on and great people you collaborate with makes a huge difference.
First 90 Days As CFO At Leaf Home
You gave such a thoughtful answer. I no longer think my question was all that dumb. Thanks for bailing me out. You’ve been with the company for several months. The first 90 days are a chance for CFOs and other C-Suite executives to make an impact and learn the business. What were your first 90 days like? What were the things you’ve learned in it, relationships and a few things that surprised you despite the level of due diligence that you did?
I’m still learning the industry. The company has done a nice job. It offers an end-to-end solution from the moment you are trying to acquire a lead to the moment you’re trying to convert that in a call center to getting a salesperson to show up at your door. I understand the high level, but I have a few more levels deeper to get through. I didn’t quite finish that.
I started learning about and understanding what business is. I’m still learning about the industry and the markets. Those are some of the things that I gave myself as challenges. I’m trying to dig in. What I found is it takes time to dig in. It takes time to spend time with the operations person, call center person and salesperson and get in there.
On the one hand, you want to give yourself time to learn so that you don’t jump in and make suggestions and recommendations. At the same time, you want to act. Finding that balance has been what I’ve been trying to do. There are some things that are done here that are different than how they were done at Rent the Runway.
One of the things that I loved over there was cross-functional work, bringing all the different stakeholders to the table and giving everyone visibility up-funnel and down-funnel. Everyone has an understanding of common transparency around where we are. Therefore, how do we get to where we want to be? That’s been a little bit of what I focused my time on. It is learning a lot, but also trying to bring some of these process needs and some of these methods of work that I found helpful in my past experience. In my third week on the job, I had the pleasure of presenting our budget to our board. That was a bit jarring.
Hopefully, it was more or less accurate.
We have a bit more time to go. It was particularly challenging to try to learn enough to be able to talk about the budget, understand it, and have some confidence. That was harder, but it’s been great to get to know the people. I realize what seems like something fairly simple on the outside is quite complicated. That’s the part that is not necessarily a surprise. It’s something I need to keep working on and continuing to learn. It’s also great to meet the people. It takes time. It’s not something you get done in several months.
The CFOs who join a hot company are going to be there for several years. The first 90 days are an opportunity. There’s not a lot of pressure on you to deliver. You can’t exactly put your feet up on the desk and say, “Call me in June.” It is a rare chance to learn, ask a bunch of questions, get to know your team and get to know the investors and the board members. It’s such a rare opportunity. From what I know about you from this conversation, you seem like you have a bias towards doing stuff. It sounds like you did take the opportunity to develop those relationships and learn what you could about the business.
That will continue. I’m a big believer in continuing to ask the questions. I was still learning up to the end when I left Rent the Runway. I’ll look back on this day and think, “I didn’t know that much yet.” I’ve not hired much since I got here, but I did hire a senior leader on my team. My advice for his first 90 days was to learn as much as you can about the business, shadow some people and build personal relationships. In the end, that is what will allow you to have an impact on the organization. Those three things are the most important. That’s what I advise them to do.
The thing about Leaf Home is it’s been a remarkable growth story. Correct me if I’m wrong, but it’s been largely organic, and you have made some of the growth through acquisitions. Is that fair to say?
We have made some acquisitions and touch-ins in some product areas.
Now the pressure is on. How do you keep that growing? How do you develop a financial strategy that’s going to support the growth expectations that your investors and others have set for the company?
I forgot to mention one other reason I’m here. Our chief growth officer here, we worked together at Rent the Runway. She went somewhere else in between, but we have an engine that works. Part of the challenge here is we’re navigating volatile markets and consumers that are uncertain at times. The advantage of this business is that we play the part of home improvement that is more needed to have, things that are about hardening your home and increasing the value of this important asset that you’ve invested in, like gutters and water filtration.
It’s one of the things that insulates us. It doesn’t mean that we don’t still have to be watchful of what’s happening in the market. Our challenge is how we think about diversifying our approach in the market. One, we were acquiring leads historically, continuing to think about additional channels that we can add, and owning more of that ourselves, which is something we think about a lot. We have a lot of opportunities to grow demographics and bring on a younger population. That’s another way to continue to propel the growth of the business.
A lot about the fact that we have one and a half million customers for a long part of the company’s history was all about gutter protection. With these emerging products, we have a lot of opportunities to sell those products to that existing base, in addition to the fact that we can use those products as a way to bring on new customers. That’s another way that we think about continuing to propel the business’s steady state of growth.
Finally, we’re only in certain parts of the home. We have the opportunity to look at where else in the home we can be differentiated. We have this model. We have these 200 offices. We have this infrastructure that already exists. The challenge is, what else can we put through that infrastructure in a way that’s good financially and cost-efficient because we don’t have to rebuild that again? Those are some of the ways that we continue to grow the business, both on what we already have and on what the products are in the future.
There are a lot of digital leaders in your space. What’s the strategy to support the company? I’m going to guess, if you don’t keep investing in innovation and R&D and coming up with new products, services and processes, someone is going to catch up to you on this. Have you thought about how you support innovation in a physically and financially responsible way?
We have a dedicated group of people constantly thinking about not only the next level of products but even the existing products. What can we do to make the products more differentiated and attractive to consumers and respond to their needs? There is a dedicated group of people who are all about more of that R&D side of the house. They’re also matched up to our product marketing team. Their job is to understand what’s happening in the market. What are the opportunities? How big are these markets? How penetrated are they? What demographic are we going after? What are they looking for? We are pulling those two together.
It’s a balancing act. We have great products. We know that we are under-tapped in terms of the potential of the market. There’s still a lot of room to grow with our products. You’re right. We also need to think about what carries growth with the business over the next few years and continually assess either evolution, products or adjacent products. That’s something that we think about all the time.
Building Strong Relationships In The C-Suite
What I’d love to chat with you about now is one of the critical relationships in a company, not just across the C-Suite but the entire company, which is the relationship between the CFO and the CEO. You mentioned you did a lot of due diligence before joining. You got to meet the players. I’d love to get your advice, even if it’s not specific to the current CEO. How should a CFO think about building a trusting, empowering relationship with the CEO?
I’m a big believer in the CEO-CFO relationship. I’m still building a relationship here. We spend a lot of time together and think about the strategies of the business and what we’re trying to accomplish. Those strategies are not just financial, they can be business strategies as well as financial strategies. This is something that is happening here. It’s similar to how it was for me at Rent the Runway. It needs to be an open and transparent relationship, with the ability to talk about anything, challenge each other and be okay with being right or wrong at different points in time. That feels like a solid relationship.

What has worked well is to have open lines of communication to think about where we are now and be able to talk about the execution of what we need to accomplish this week, this month or this quarter, as well as being able to talk about where we want to be in three years’ time and working backward. What are the things that we need to be able to accomplish now? What do we want to put in motion? Those have been some of the things that have worked well.
In my prior role, we got to a point, and it was most obvious in our earnings conversations or conversations with investors, where I could talk about the business and the strategies around the business. She could talk as easily about all the strategies around finance, understand each other’s thoughts, and complete a full picture of the company. It’s important to create those relationships. Start with open lines of communication and think about what’s best for the business. If you have commonality, mission and goals, pushing each other in certain areas is healthy and appropriate. I believe in different perspectives. The complementarity is strong.
You need to challenge people. There was a quote I learned years ago. “If two people always agree on everything, one of them isn’t needed.” They need you to respectfully disagree from time to time. Given your business model, you have a productive relationship with the CIO. Technology is such a core part of everything about your company. How do you develop that relationship in particular?
Similar to the relationship with the CEO, we’re developing it. My approach has been to spend a lot of time with my peers and to have a chance to dig into their areas. Our CIO and I meet weekly. We had a chance to talk about some of the business’s efforts in terms of what she’s working on. We are a tech-enabled business. Tech is at the core of what we do. We want to move away as much as we can, and we have moved away from, many of the manual processes that existed for the company, particularly in the field, to more automated processes and things that allow us to help with efficiency, cost and administrative workflow.
These are things that we work on together, but what is the roadmap for technology? What is it that we’re trying to accomplish? We’re in the middle of a significant CRM implementation for Salesforce. That’s something that encompasses the whole business. She and I are working closely together because there are a lot of costs, but it has a good impact on the business. We want to understand what we are doing. What are some of the trade-offs around some of the other projects that we’re working on? What are the priorities?
It’s a strategic relationship. It also can be quite tactical to think about the prioritization of what we work on and make sure that we’re thinking about the financial impact and return to the business. We’re making sure that not only the two of us are thinking that way, but we’re also hoping to disseminate that message throughout the business. How we’re partnering together is holding people accountable to understand the impact of what they’re asking for in terms of technology needs or software development.
There’s one thing about you that I thought was a little interesting, Scarlett. You’re on one board right now, but you’ve been on more than one board during your career. I’m always curious, how does being on a board impact how you execute your role as a CFO?
I’m only on one board, and it’s a private company. It’s a company that I’ve been with for many years. I started with the company as an investor. I represented an investment as the investor on the board, but I’m an independent on that board. I’ll talk about that for a second, but I’ll widen it quickly. It’s been helpful to be on that board. I enjoy the board interactions. It’s a different involvement. It’s not the day-to-day involvement. You get a chance to be closer to the business, to understand more of what’s going on, but you’re not the one operating or driving the day-to-day decisions of the board. It’s always helpful to have other board members around the table.
Their perspectives and experiences are what I enjoy about it, in addition to the fact that what they’re doing day to day could be relevant to your business. It is less relevant to my business, given that it’s in the fashion space. It was interesting to be on that board when I was at Rent the Runway because they might be approaching the market in a different way than we were. There was some interesting learning that I could bring back in both directions.
What’s interesting about being on a board is I now realize how painful it may have been as a board member when I was an investor. You don’t have an appreciation of what it takes to get things done. It’s easy to sit in the board seat and say, “Why aren’t you changing strategy? Why aren’t you approaching the market in this way? Why aren’t you selling a different product?” Being here, I realized those things take time. There are strategies, iterations and errors to be made and learned from.
That has to happen for something to show up in a boardroom, which is difficult to appreciate until you’re yourself an operator. That’s why I’m here. It’s because I had that curiosity. I was always wondering, what is it like on the other side? The CEO appreciates me more now. I feel her pain. I can appreciate the challenges. When I was an investor, I would ask the question, “Why aren’t you doing it differently? Why can’t the numbers be a little bit better?”
When I was a CFO, it was with venture-backed startups. They were good business people. They weren’t unreasonable by any stretch of the imagination, but often, they’d ask dumb questions that they thought were penetrating and thoughtful. They own the company, and you have to be respectful of everybody, particularly the people who own the company. It’s like, “Why didn’t I think of that? Do you think we didn’t consider that? Do you think I can snap my fingers like Thanos and make it happen?” For some reason, I’m making far too many pop culture references on this call. Tell me you know who Thanos is, at least.
Who, what?
You’re killing me. He’s the big purple guy who snapped his fingers and wiped out half of civilization. Your daughters probably know. I always like to ask CFOs about work-life balance. In your case, it’s difficult. You’ve got a busy job as a CFO, you’re on a board and you have two college-age daughters. You have a lot going on. How do you find the time to do all of those things and find me-time? You have some hobbies that are outside of all of those things. How do you approach it as best you can?
The best I can is the perfect way to put it. It’s a challenge. I continue to learn here. I have found it difficult at times, to be perfectly honest, with the work-life balance. It’s a little bit easier now that the kids are in college. They’re not there when I get home. When they were younger, I was trying to find the time to do my job, to be a mom, to try to have some hobbies and to spend some time with myself and my spouse. It’s a lot.
I find it difficult to find that work-life balance. I needed a moment to recharge. I took several months off between jobs to go and take that time back for myself and spend some time. I’m trying to be much more intentional now. I came in here with that thought in mind of not allowing myself to be consumed as much as I have before, as exciting as it is because you have a passion for a business and you’re excited about the mission. I have a passion for this business, but I’m trying to be much more intentional.
I have a couple of silly examples. I’m now within a reasonable commute of my office. This is two miles. I’m trying to walk at least one of the times that I’m going into the office. It’s mechanisms like this. I want to try to spend time with my family. My kids are home from college. I’m much more mindful about being home and spending time with them because I don’t get to see them as much anymore. I build time for hobbies. Anytime I can get out there, I play a little tennis and try to do some hobbies. I find that’s a good way to decompress and take my mind off of work. I’m trying to be intentional. It’s an important example for your team and peers for them to see that.
What are your daughters studying? Are they following your world into business?
One of them is pre-med. She’s looking at the medical field, and the other one is studying psychology and children’s studies. She’s trying to figure out what that means. We have yet to see. It’s neither near finance. I don’t know whether it was looking at me or not, but they’ve chosen different fields.
It’s good for them. They’re fellow MBAs. I worked hard. I created a lot of jobs along the way, as did you, and I did a lot of good, but they were motivated by a desire to help people in a more tangible way than you and I did. It’s admirable that they would go into those fields of work.
I’m thrilled for them. They’re both excited about what they’re studying and what they’re getting to see. I’m happy for them.
I always ask people for fun facts, but you gave yours away earlier, saying that you grew up in France and you’ve spent a lot of time in Europe. Did your daughters get to live in France at any point along the way?
They haven’t lived there. They’ve lived in a few other countries because not only was I an expat child, but we did that to them. They were both born in London. They traveled quite a bit, but they did not live in France. We go back quite a bit. My family is not far away. We go back once a year if we’re able to. Those times are precious now. We’re going to try to do that again.
Advice For Aspiring CFOs
I’m always jealous because I’ve lived in Massachusetts and New Hampshire. That’s it. I’m the most vanilla human being on the planet when I talk to people. My concluding question, Scarlett, is you had a great career and are learning along the way. What’s your advice to the next generation of CFOs? What should they be thinking about to attain the role if they haven’t yet and flourish once they do?
There are a few different things. I’m an example of the fact that the path is not linear. Going into a CFO role was an experiment. Take the risk. Go after that experiment. This is my third career. You can get there in many different ways, and that’s okay. There are many ways to get the CFO role if that’s something you’re interested in.
The second thing I would say is the importance of relationships. Both my Rent the Runway experience as well as the experience here first came about because of people I had worked with historically, and we stayed in touch, especially people that you value and respect. Stay closely in touch with them. You never know where those relationships can take you. I’ve mentioned the mission. When you work with a single company, the importance of mission and believing in the product and the services that the company stands for makes such a big difference because there will be ups and downs, as you know. To have that to live by is critical.
Finally, we’ve talked about the importance of people. If you’re in the role, having a great team, hiring people who are experts in their area, and who know way more about those areas than you will bring up the whole team as a result. Those would be some of the most important things. When it’s time to take a break, take a little bit of a pause and recharge.
Scarlett, this has been a great conversation. I know you have a lot going on. I do want to thank you for your time. I always like to let the guests have the final word if they want it.
Jack, I wanted to thank you. I enjoyed the conversation. I appreciate you reaching out. It was a great discussion. Thank you.