Human capital is one of the most important bloodlines of any company, and building a people-first culture is key to keeping it healthy. Dorothy Walter, CFO of Alpine Investors, shares how the company unlocked growth and achieved success by focusing on human development and talent retention. In this conversation with Jack McCullough, she explains why empathy in leadership goes a long way in maintaining a strong team and shaping the next generation of financial leaders, how to use AI and automation to your company’s advantage and what she learned about persistence from cycling across the United States.
Listen by clicking below. The Q&A, lightly trimmed and edited for clarity, follows.
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Listen to the podcast here
You are going to love our guest. I am joined by Dorothy Walter. Dorothy is the CFO of Alpine Investors.
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Dorothy, welcome to the show.
I’m so excited to be here. Thanks for having me.
A little bit about Alpine, and I’m going to let you fill in the blanks. You’re a people-driven private equity firm investing in software and services businesses that are navigating transitions and scaling through change. How’d I do?
That’s right. That’s exactly who we are. We are a middle-market, private equity, leveraged buyout shop with a focus very much on companies in transition, companies where a founder has seen the end of the road and wants to make sure his or her company is going to the right owner. We work very closely with those founders to transition management and show them that their company is in the right hands.
We manage over 25 companies, but that doesn’t represent the breadth of what we do. We invested in over 170 companies in 2024 as part of those over 20 companies, and integrating them into a broader vision that we have for each of those industries and each of those services that we’re building. We work day-to-day with the people on the ground who own those companies and who are running those companies. That’s one of the reasons why being people-driven is so important for Alpine as an investment manager.
That’s great. Is there something that people maybe don’t know about Alpine that might surprise them?
A little bit of what I touched on is that we replace our management teams every time, but we do so in a way that’s collaborative. Private equity sometimes has a bad reputation for firing a ton of people after they buy a company or doing other things that might be damaging to the operations that have been set up. We seek to work in collaboration with the founders of their companies to understand what makes their company unique and what makes it tick.
We then introduce them to their next CEO so that they can get to know the person who’s going to be running their company and who’s going to take their baby into the next phase. I find that wonderful how we help founders manage that transition. Those companies then get integrated into broader companies that we own, the bigger companies. Eventually, we’re looking at companies with multibillion-dollar revenue built brick by brick from founder-started enterprises. That is very motivational for us.
It is an exciting business model, and I look forward to returning to it, but I want to get into your own background a little bit first. Can you share where you grew up? I found it interesting.
I was born in Taiwan, and then we moved to New York and Singapore before settling in the early ‘90s in Beijing, China. For those of you who know history, the early ‘90s were an interesting time for China as a country. Post-Tiananmen, the country was opening up to involvement in the broader global universe. We were some of the earlier expats to move there.
I count myself as so lucky to have seen the city of Beijing when there were more bicycles on the street than cars. There were donkey carts being pulled through the capital city. We grew up eating sweet potatoes off of oil cans being roasted in the street, walking around and enjoying the sights of a very ancient city that was on the cusp of modernization.
That must have been a fascinating time to have been there.
I was lucky. My father and mother moved there. They were some of the first American exchange students to be invited to study in China in the late ‘70s. They moved there because we had connections. I’m part Chinese. My mom has family there. My father was helping Chinese companies go public and access public capital for the first time.
Back then?
Yes.
He must have been one of about three people doing that.
It was very early times.
That’s fantastic. That’s another interesting response there. What was your first ever job?
My first job where I got a paycheck or my first professional job?
Your first job when you were a kid, maybe a teenager, or something like that.
I worked on a farm in upstate New York. I loved that. It was so important to understand how to live in tune with nature. It was a beautiful farm called Sprout Creek Farm, which it was run by nuns from the Sacred Heart. It was a cheese production farm, and it was also an educational farm for children. Being a camp counselor there and being a farm hand taught me to wake and go to sleep in the rhythm of the sun, and also the value of nature in our lives, and having children be able to access nature.
What a fascinating job. I like to ask that because my first job was at Burger King. Burger King, McDonald’s and Wendy’s are a pretty common response. I found out your first was at a farm.
On the upper part of that supply chain.
Educationally, you studied economics at Vassar, and you minored in German and Russian. You didn’t take the easy way out, for sure.
I am appreciative of my liberal arts education. I don’t know if you have many CFOs who chose that route. I double majored in economics and art history and double minored in German and Russian. For me, being able to access different parts of my brain was important in that liberal arts environment. It gave me something for life, which is fulfillment in my life outside of my professional career.
While economics relates directly to what I do on a day-to-day basis, art history and languages are things that I carry with me to make my personal life more fulfilled. That helps make me a better professional at the end of the day because I’m a 360-degree individual who can look at things from different perspectives and also find stress relief easily accessible through other hobbies that I have.
That’s fascinating. I won’t say there have been zero of my guests who majored in liberal arts, but it’s pretty small. A lot were economics undergrads. A surprising number of scientists became CFOs over time. It makes sense either way because liberal arts are good communicators. You went to one of the best schools on the planet for that kind of thing. I think of scientists as problem solvers. If you consider accounting and finance to be table stakes, those are the two most important skills that CFOs do in the modern world, right?
That’s right. Especially with all the data that we’re dealing with, having a science background is important.
I graduated from college in the mid to late ‘80s, in 1987. Ninety percent of the CFOs my age, at one point, had my background. We all had the same resume. Business undergrad, Big Eight accounting firm, controller, CFO. Unless there was something unusual in your background, that’s how you became a CFO. Now, anybody who’s a strategic thinker, transparent communicator, good communicator and understands finance and accounting enough can get the CFO role.
That’s an interesting distinction. The multidisciplinary aspect of it is very important as you think about the future of what’s going to be asked of people in this role.
It makes sense. After Vassar, you got an MBA from another school that I’m not familiar with. Is it Stanford? They must not have much of an MBA program.
I took a brief hiatus of six years in my first job. Maybe I’ll tell you a little bit about that.
I’d love to.
It’s an interesting story. My art history professor, or, distinctly, the director of our art museum at Vassar introduced me to private equity. How is that possible? I got a private equity job coming out of a liberal arts school right out of undergrad in 2007. He referred me to a very boutique art lending shop that had a few people working there who were underwriting art as an alternative asset. I found that fascinating. I love the world of alternative assets. I love the intersection of finance and art.
They were a small shop. They couldn’t give me a full-time job. The founders of that firm introduced me to one of their co-pro professors at Columbia Business School at that time, who was starting a private equity fund of funds. It was supposed to be a lunch, like, “Dorothy, go have this lunch with David Sherman. He’s a great guy.”
He is a great guy, and that lunch turned into a whole day of talking to his team as he was about to launch this new fund to fund strategy. I got in at ground zero right out of undergrad and got to see how to build a private equity investment management firm from the ground up, starting at age 21. I’m grateful for that experience, and it came to me through my art connections, which is unusual.
What I did there was twofold. I did mention it was 2007. Most of my friends who studied economics took jobs at Bear Stearns and Lehman. They said, “Sayonara. See you later. We’re off to the good life.” We all know what happened a year later. For us as real estate investors, we had thousands of properties that were exposed to the financial crisis.
My job in the first two years at the firm was to understand how to underwrite that risk, how to identify it across thousands of properties and then how to go after it with proactive management strategies. I’m grateful to my mentors in that job for teaching me that skillset quickly. It was a time when most firms didn’t have a ton of software to support in gathering data or managing data, so it was hand-to-hand, brick by brick, building up a database, analyzing that database and then implementing strategies to contain risk. It was a wonderful time to be alive as someone who is interested in finance.
From that role, I moved on to the investing side. I worked on the investing side of that business for four years, finding first-time managers who were trying to raise money for their first fund, underwriting their investments to ensure they were sound and then negotiating with them on how to get their funds off the ground.
For me, that job was invaluable in that it gave me perspective on what it takes to scale a private equity investment management firm, how to underwrite managers and how to manage risk. We started from scratch, grew to $3 billion in assets and were acquired by the Carlyle Group. It was a lucky punch for me. I was so grateful to have that as my first job. From there, I went to Stanford Business School because I had to ask what was next. All of my friends had lost their jobs and had one, two, three or four jobs during that timeframe, and I had one. Stanford opened the door for me to other opportunities.
That’s fantastic when you think about it. Twenty-one, in Massachusetts, would’ve barely been old enough to drink, and you’re having all of that thrown at you. While I appreciate your saying that it was luck, I’m sure you worked your butt off and brought tremendous value to the organization. It wasn’t all about being in the right place at the right time.
I do think luck has a lot to play into it. You can try to be as calculating as you want about your career, but in the end, it’s open to fate.
You can be the smartest person on the planet, but if you grew up in a third-world country, you’re not going to have the same opportunities as some other people might. That’s the way it is. That’s a fantastic story. I think of everything you accomplished by the time you were 26 or 27 years old. You decided to get your MBA from Stanford. For those who are reading who don’t know my sense of humor, I’m aware of Stanford. It’s an elite program. I went to Sloan. Stanford turned me down, but I don’t hold a grudge all these years later. What was that experience like, going to Stanford and focusing largely on business-type stuff?
I felt very lucky to be able to go to Stanford. It was my dream school because the unique approach they bring to the MBA education is a holistic focus on management style and on not only unlocking your own personal potential, but seeing that and unlocking that in others, which has been carried with me through the rest of my career.
Going there was a wonderful opportunity for many reasons. One of the things I did to take advantage of that was to experiment with different career paths. It was a time when I could take risks and not have to worry about it. I’d been in the same job for over six years, and I was curious, “What is it like to work at a startup? What is it like to work for a venture capital investment firm, not a private equity, real estate investment? What is it like to work in a company in an operating role?” I’m grateful that the Stanford MBA opened up those doors for me, and I could experiment with different roles and see what resonated the most.
Ultimately, what I found is that while I loved investing and I thought that that was going to ultimately be my goal, leaving business school, I was so good at operating. I threw my heart into it. What I realized in an operating role through my internship I had in the summer at Apple was that I was motivated by collaborating with different people.
When you are in the finance industry and investing, you’re speaking the same language to everyone you’re working with, whether it be lawyers, accountants, tax consultants, your investment committee or your investors. Everybody understands the language of investing. When you’re in an operating role, you have to explain that to an engineer, a senior marketer, a design director or somebody on the technical side. For me, that was a wonderful challenge. I ended up going to Apple after my MBA.
That’s probably a solid choice coming out of Stanford to go work for Apple. You worked at Apple and the Carlyle Group. You’re focusing on almost different sides of the brain in some ways. That seems to be the way you like to roll.
I’m not going to lie. Going from an investment firm to an operating finance role was harsh. I remember my first few months at Apple. I was working with colleagues who were extremely experienced, and they were doing things like closing the books and forecasting the P&L. I had a seat at that table, and they were looking at me like, “What are you doing? Where’s your forecast landing? What are you going to report for the quarterly earnings call?” I was like, “Excuse me? What does that mean? How do I do this? What’s SAP?” It was an extremely humbling experience.
A few months in, I remember over the holidays I was crying on my parents’ kitchen floor, being like, “I don’t know how to file for an accrual.” Thankfully, I have some lovely colleagues at Apple who held my hand through it and taught me the ropes, so about 6 months to 12 months in, I was sailing. It took a lot of hard work to reposition my career. It was very humbling. I’m glad I took that risk.
Good for you. I talked to a lot of CFOs. Few, if any, didn’t have critical mentors along the way. You’ve referenced a couple, but I’m wondering if there are some that particularly stick out as, “He or she made an impact on my career and how I approach it.”
Maybe fast forward, after Apple, I ended up taking this job at Alpine. I was 33 at the time. It was daunting to take the CFO title at 33. Billy Maguy is a founding partner at Alpine. He had held that CFO title since the inception of the firm. I am grateful to him because he sat me down day after day, week after week. It was drinking from the fire hose of Billy Maguy’s brain. Trust me, at times, it was like, “I don’t know what you’re saying,” because tax structuring is complicated.
I’m so grateful to him for taking that time to invest in me and download everything that he knew, and not only that, but he trusted me to take the role and do it my own way. Once he felt, “I’ve given you my knowledge. I will step back and let you operate the way that you feel fit,” I find that that is the most valuable thing that I’ve been given in my career.
That’s fantastic. This is a good natural segue to Alpine. You took the job in 2018, if I have my facts correct. You’re coming up on seven years. What was it about Alpine? It was a great choice. You’ve had a wonderful seven-year run there. How’d the job come to you? What was it that made you take it? You were working for what some would argue is the world’s greatest company in Apple.
It was hard to leave Apple. I had a lot of friends there, and I still have them. I loved working for a company where the values aligned with mine. I got to see my work being announced on the world stage. That is beyond motivational. At the time, I was thinking about how, over time, I would develop expertise at Apple that could be used in other ways, for example, to help companies prepare for IPO. Alpine reached out, and I ignored the recruiter’s message for months. I thought, “I don’t want to be CFO at a private equity firm. I was on the investing side. Why would I take an operational role? Why not go be an operator where I can have the guts and the glory like a Series D company and take it public?”
I started to notice as I talked to the founding partners at Alpine some similarities with my first job. That first job, we saw that company start from scratch and go on to be acquired by Carlyle. I could see Alpine was still small. We had about 20 employees and $1 billion in assets. I could see the motivation in the partner group and, frankly, also the humility and the kindness in the founding partners that reminded me of what I loved about my first job, so I took the leap.
It was that pattern recognition that allowed me to give up what was arguably a wonderful job with a significant trajectory to go to what was, at that time, a very small private equity firm. Since then, we’ve scaled 18 times in assets. We went from $1 billion in 2018 to over $18 billion. We went from 20 employees at that time to over 180 employees. We have three offices in the United States, potentially embarking on our first international investments this 2025. It’s been a wild ride.
Good for you. That’s exciting. It clearly was a great decision, but one that, rightly so, you thought long and hard about before making. Kudos for making the right one. That’s quite a success story. One thing I’d like to explore is that it’s not like a traditional corporation working for fun like that. Particularly, you said there were 20 people when you joined or something like that.
That’s right.
You all know each other pretty well. You’re growing gangbusters. There is a lot of pressure, and you’re having a lot of fun. How do you build a relationship with the CEO and the entire leadership team at a firm like that that’s going through such a dramatic change?
I learned that skill when I was at Apple. Angela Ahrendts, who was formerly the CEO of Burberry, had joined Apple around the same time I joined to oversee the retail unit. She was one of my key business partners. She was investing significant dollars and new initiatives for retail at the time under Tim Cook’s direction. Her project was given to me to manage.
At first, people thought, “Give it to Dorothy. Let’s see what happens. It’s going to be fine. It’s probably a side project. We won’t have to worry about it too much.” I started to ask deeper questions about not only the financials of what she was proposing, but the impact on our customer base. What I learned from Apple is that you put the customer experience first. That’s a Steve Jobs tenet. That’s something that we always keep in mind.
I started to realize that what Angela needed to know from me and what she wasn’t getting was not just the financial performance of these initiatives, but the impact on our reputation and our brand, where we had opportunities to further engage and push for Apple and markets that were new to us. Starting to capture that new data for her allowed me to open up a door to speak directly to her, which would’ve been unheard of at the time, given how senior she was within the organization.
I take that same approach with Graham, our CEO here at Alpine, of putting our customer first. In this case, that is Graham. What does he care about for the firm? How can I leverage the knowledge and the data I have to tell a story that will engage him and allow him to make better decisions? What is top of mind for him?” I’m grateful to have learned that skill at Apple.
That’s fantastic. I want to talk about the culture at Alpine. You have very much a very people-first culture. That’s something that’s pretty easy to say. Everybody says it, but you live it. It’s an absolute lifestyle and commitment. Let’s talk about human capital. You have a unique approach to attracting the best talent and, as importantly, retaining it. Can you share a little bit about your philosophy and approach to doing that?
There’s so much here. I could do the whole episode on this. Maybe I’ll talk about it from a personal perspective and then extrapolate. When I was interviewing for Alpine, part of my interview process was conducted in three hours in a closed-door room. It was a nonstop barrage of questions. They were not case study questions. They were not technical questions. They were questions that were testing my emotional intelligence and what Alpine calls the adversity quotient. How do you respond when things don’t go your way? Does that make you a stronger person, or does it set you back?
We drink the Kool-Aid. We employ these interview techniques at Alpine as well as across all of our portfolio companies. That allows us to vet our leaders for not only the typical things that you would seek in a CEO or CFO technical acumen and professional background, but also this adversity quotient and, at the end of the day, empathy.
It was interesting to me that KKR started going public with their empathy gyms for CEOs because they did some research and looked at, “Which of our companies is successful?” They looked at companies in the same industry with relatively the same customer base, and one company would outperform the other, even though they were providing the same tools to each company.
They did a correlation, and what they found is that if their CEOs have empathy, the company’s performance tends to go through the roof. They’re making their CEOs go to empathy gyms, which I am very curious about what intellectual property they’re building there. We didn’t even need that because we tested for that at the outset. We make sure that all of the people who are leading our companies bring that to the table on day one. That’s through our interview process.
How do we hold people accountable? We conduct quarterly employee engagement surveys at all of our companies and at Alpine to measure employee engagement. We need to see those numbers either staying flat, which hopefully not, or improving over time under our leadership. That is a thing that we report to our investors on because we believe it’s truly a leading indicator for how a company will perform. You don’t want to be measuring revenue. You can say after the fact, “We didn’t hit our targets.” It’s not giving you any information. If you track a leading indicator on employee satisfaction and engagement, and it’s going down, I bet you your financials are also going down.
That’s fascinating. I want to make sure I heard you correctly. Did you say empathy gym?
I said to myself, “Why is everyone using this gym analogy these days?” You don’t have to have a lot of muscle to be a good leader, but that’s okay. They can use whatever phraseology they want. Our empathy gym is called the People First Leadership Program, and we like it that way.
There you go. I love that. It’s interesting that you’ve mentioned empathy a couple of times because a few years ago, I did a survey, not of CFOs, but of people who rely on CFOs. A lot of them were PE and VC investors, CEOs, board members, and other C-Suite members. I said, “What are the qualities you value in a CFO? You can’t say finance and accounting.” Number one was empathy. In fact, there was an acronym. Transparency, Resiliency, Inspiration, and that’s more inspiring, confidence and trust, Collaboration, and Empathy. It was interesting. That seems like even if you never thought of it in such terms, that might resonate with your firm.
It does across the leadership spectrum, not just CFOs. People tend to emphasize it with CFOs because you may over-index on the technical skills when thinking about what makes a great CFO and under-index on some of those softer skills. For me, building those soft skills has been integral to allowing me to partner better with every business that I’ve worked with.
That makes sense. Earlier, you mentioned, your AUM grew 18x during your tenure, which has not been very long. That’s exciting, but it’s not easy. What are some of the big challenges, and what infrastructure did you put in place to support the growth without killing the entrepreneurial spirit that’s essential to growing like that?
You name it right there. I appreciated the processes and the best practices I observed at Apple and understand that it takes years to build infrastructure like that. I also realize that you can kill the spirit of the firm if you do that too quickly. For Alpine, it was about that balance. When I joined, I had three people on my team, an office manager, our fund accountant and our management company or our corporate accountant. I was responsible for nine or 10 functions, everything from cybersecurity and IT to compliance as a registered investment advisor to fund formation to investor relations. You name it. If it wasn’t investing, I was covering it.
If you’re faced with rapid scale and very few resources, the first thing you do is roll up your sleeves and do it yourself. For me, I can’t say I had work-life balance in those first two years. We were raising a $1 billion fund. We didn’t have a fundraising team. We didn’t have an investor relations team. We didn’t have databases with reliable data. I’m grateful for that time because I found that I love going deep and then building on that and building for permanency. If you understand at the core what the business needs, you can recommend better options for the long-term.
From there, we made decisions on who to hire and how to hire people who could grow with us, who were willing to stretch out of maybe their current roles. We made decisions on what to outsource, what service providers we could rely on and who could also grow with us, and tested them on that. We also, thirdly, brought in technology, which I know you’ll ask about, thinking about which parts of your process flow you upgrade through technology.
A final example I’ll give here is that my very first hire was an assistant controller on our fund accounting team. She had come from PwC, had a background probably like many of your readers, had been in audit and practiced there for almost a decade. She is our head of investor relations, and she is good at it. Why? It is because she understands all of our fund financials. Not only that, but we stretched her into being able to tell stories and build relationships. She’s a killer head of investor relations. Most shops would’ve hired someone laterally who had already done that before. At Alpine, we believe in unlocking people’s potential.
That’s fantastic. Since you mentioned it, I am legally required to ask you about digital strategies and technology. You referenced it, but how do you use digital technology to support the company to drive growth? In my day, it was to invest in technology, save money, and be a little more efficient. Now, it’s a necessity and a competitive advantage. How are you taking advantage of all the tools that are out there?
I don’t want to be a broken record for people, but people are core to what any organization does. If you are bogging down your people with non-value, additive, repetitive, heavy volume processes, over time, they will lose their edge. To give an example, in our industry, we’re a registered investment advisor. The SEC oversees all of our activities. That creates a ton of reporting and a ton of oversight processes that are required and that are also creative to our risk management, as well as outside of being a registered investment advisor.
If you were going to do that properly, you would have to comb through hundreds of thousands of pages of documents of obligations we have to each individual investor, obligations we have overall to our broad pools of investors, obligations we have to the SEC, and obligations we have to other administrative bodies. The people who are going to want to do that work are different from the people who are going to take your organization to the next level.
The technology helps you take top talent who’s motivated and wants to transform an organization, but also enables them to do the day-to-day parts of the job that require detailed orientation and significant consolidation of data. That’s where we’ve seen the most benefit. We use AI tools for contract review. We’re looking into AI tools for recruiting and hiring across the business, where we have high-volume processes and our talented people can get a leg up. We’re going to employ them because that’s going to help us retain top talent over time.
That makes sense. I want to shift gears a little bit because when we spoke, you mentioned something which I found interesting. You’ve established almost like a community for the CFOs at your portfolio companies. I’m curious if you could share a little about what motivated you to do that and how you interact with the portfolio company CFOs. Does working with them change how you approach your day job as CFO at Alpine?
Yeah. We built that community from scratch, from the very beginning of joining, mainly because I wanted peers. I wanted someone who would share my pain. It was homegrown. Over time, we have a wonderful team that manages that community and is more hands-on than I ever was. It was critical for us in two ways. One, in the past couple of years, we’ve had very disruptive macro events, such as COVID and the Silicon Valley Bank crisis. Having that community up and running and being able to coordinate a response across our CFOs was critical.
Having that first-name basis and they have my cell phone number in those moments kind of relationship allowed us to manage risk. This goes back to my very first job when we were in the middle of the financial crisis, managing a portfolio of thousands of real estate properties. You have to have a pulse of what’s going on on the ground. Those relationships helped us be a better fiduciary to our investors because we knew exactly where the risk was, and we could pinpoint it and address it ASAP. Number one, it helped us in both of those crises to have those relationships.
Number two, when you’re not under duress, being able to share best practices. If one CFO is looking at interest rate hedges and has gone through all the brain damage of what structure is best for their company, shouldn’t we share that with everyone else so they don’t have to go through the same process? It has been wonderful. Frankly, I’m inspired by what they’re doing on the ground. Their jobs are much tougher than mine.
In my career, I was a portfolio company CFO. I won’t comment whether my job was tougher than the CFO of the fund, but my 33-year-old self is happy to hear you acknowledge how difficult that job is.
It’s very difficult. It is tougher because I can predict our top line much easier than you could.
It’s interesting because the role of the CFO is changing. More than most people, you probably have a front row seat to this evolution. How do your own responsibilities change with the environment, and also, how about at the portfolio level?
I would say something similar to what I spoke about in terms of how we come together during times of crisis. I wouldn’t say this is a time of crisis, but it’s a time of uncertainty. It is making sure that we have a pulse on what’s concerning our company management teams and what leading indicators, like employee retention, employee engagement, and other leading indicators, we can track to ensure that we get ahead of problems before they manifest.
One of the things we’ve done as a firm is form a portfolio oversight committee that before any decision is made by our investment committee, which is our true governing body, this committee helps our board members and our executive teams think through problems and try to give them resources that they can tap into before they become a real issue. We’ve built out a whole operating group to offer services around go-to-market, pricing advice, financial systems and technology to be able to advise people and give them quick access to advisors whom we trust.
That’s fantastic. That’s insightful. I like to say that CFOs no longer record history. They make history. It’s amazing for me to watch it happen. It must be for you, too. Are there any particular areas that CFOs need to start being more involved in than they were in the past? Evolutionary-wise, I was the old-school general ledger, CPA, accounting, and finance, and I was good at it. You represent the more modern version. Looking forward, what should they be focused on?
You can never go wrong with the people process technology framework. A lot of CFOs like to use that to guide where they spend their time, but I don’t want to talk about that. You have to win on all of those fronts, but for me, where I’ve found the return on investment to be high is investing in people development. You need to hire the right people, but you need to be asking yourself not only what are they doing this year or next year that’s going to advance the ball, but how are you then going to develop the skills in them that serve the company three and five years from now and get them motivated to stretch that way?
That can be a tough question when you’re managing an accounting team. A lot of accountants are happy doing the audit and happy doing that year after year, and that is wonderful. That is a necessary skillset. It’s a deeply appreciated skillset. I want those accountants to know that they have so much to bring to the table from their understanding of those processes, the controls that we put in place, and our reporting standards.
Think outside the box. Think about how we can use AI to improve our day-to-day processes, improve our cap table management, improve our valuation processes, and cut down the time it takes to produce the financial reporting for our investors. I want to tap into that deep knowledge of our team and help them understand that you can deliver on these consistent asks year over year, and you should be pushing yourself to ask, “What’s next? How can I uniquely contribute?” That’s something that if CFOs do it right, you will see a whole new level of influence from your team.
That’s wonderful. I want to change gears a little bit. A lot of people in your position are on boards of directors that do philanthropic work. I’m wondering if there’s anything in your life that you’d like to talk about.
I was lucky enough, a few years ago, to be asked to join the Point Reyes National Seashore Association board. They are the nonprofit partner to Point Reyes National Seashore. It’s a drop-dead, beautiful corner of the world, about one hour north of San Francisco. That place has a lot of meaning to me. When I first moved out to California, I would go hiking there to clear my head and make big decisions. Before I left Apple, I went for a hike there solo and thought about my life and what mattered. I got engaged there. My son is named after my husband and I’s first favorite hike out there.
My whole life is so intertwined with Point Reyes. To be able to serve on a board in a treasurer function and advise on nonprofit finances, which is a different part of the brain, is a deep honor for me, especially when we want to make sure people can have access to the outdoors who may not historically have access. You might not own a car, so you might not be able to drive there. Some people living in the Bay Area have never seen the ocean in their lives, which is a travesty. We want to try and make sure that even disabled people can have access to the nature that we love and that so deeply changes us as people.
That’s a wonderful cause to be involved in. Good for you. One of the questions I like to ask has always been critical, but there’s increased awareness of it. It is the concept, to the extent it exists, of work-life balance. Here you are. Young family, fast-growing company and working on the board for this terrific nonprofit. What’s your secret to doing it all or doing as much of it as you can, at least?
I have to admit. I listened to your show and I listened very closely to all of your other CFOs and how they answered this question because I wanted to uncover a kernel of truth and a strategy, if you will. I don’t know if I can offer a strategy. I’ll tell a story. I had my first child a few years ago. He was in the NICU for five days. I was in the hospital. I almost had a stroke with postpartum preeclampsia.
My husband, at the time, had started his own company. A majority of his employees were in Germany. He has an AI machine learning tech startup. After chartering us in that hospital through a life and death experience, he stayed at home for a little while and then had to go back to work. He barely took any leave. There I was. I struggled through those first couple of months of being a new parent and went back to work.
As a mom with a newborn, you don’t get any sleep. At the time, at work, we were running a $3 billion transaction, which was the largest of its kind in the industry. My team had been wonderful. They were pulling all the stops and had everything lined up. I had a niggling anxiety in the back of my head, and I couldn’t tell whether it was anxiety because I’ve had zero sleep or anxiety because there was something with this transaction that I’m not comfortable with. It was very hard for me to operate at my best. I was sleeping on the floor next to my son’s crib or dealing with his crying 24/7 outside of work, and then being asked to perform at the highest level and being tested by this transaction.
In the end, what I will say is that you have to persist and trust yourself. At the end of the day, I trusted that anxiety. I went deep into the hundreds of pages of the legal docs that had been drawn up for this transaction proposal and mapped out the economic terms against what we had wanted to offer to our investors commercially and what the lawyers had put down on paper.
There were some tweaks that needed to be made, and thank goodness I trusted my gut. It was very hard to trust my gut in that situation. We ended up making those tweaks to the transaction to the benefit of our investors. I’m pleased that we did that, and we upheld the strongest institutional standards for a transaction of that size. It’s challenging. People in a male-dominated environment may underestimate what it takes to get through those first few months of nurturing a young life in this world.
I want to thank you for sharing that and showing a vulnerable side. Let’s face it. It’s not easy for financial leaders to do that. For work-life balance, I know you have some interesting hobbies outside of work, too. There was one in particular that you shared, but does anything come to mind that you’d like to share with the audience?
Thank you. I’m not good at work-life balance. The one thing I would say is that I focus on two things. I focus on delivering at my job, my son and my family. By cutting everything else out, I’m able to show up well in those circumstances. You sacrifice. I don’t see my friends very often. I also used to have cool hobbies that I don’t do as much anymore. I was an avid cyclist for many years.
One of my favorite memories and one of the best things I’ve ever done in my life was cycling from Anacortes, Washington, to Albany, New York, with my father, unsupported. It was just the two of us on our crappy little bikes with panniers. I had probably one normal person outfit, two cycling outfits, and a ton of energy bars and peanut butter.
We made it across one day at a time. You learn a lot in that. You get very close. I got very close to my father. I have a deep appreciation for the American pioneers who made that trip in their covered wagons. It teaches you something about persistence. I might link that back to my story about work-life balance. You have pain from the bike seat every day. It doesn’t go away after 50 days.
To do that, and then to keep on going, not knowing where you’re going to end up, not knowing where you’re going to sleep that night, not knowing if you might be in a food desert and you have to eat Doritos for dinner after cycling 80 miles, getting through that, and seeing the reward in it allowed me to get through a lot subsequently. Persistence is very important. That’s what I took away from that trip, and also a deep love for this country and the people in it.
That’s fantastic. I’m a father of sons. I love the fact that you and your dad have that type of relationship that you could do that. I’m not even sure how I would’ve suggested that to my mother.
It was a joke. I suggested it as a joke. I said, “I got into business school. Let’s bike across the country.” Two weeks later, my dad had bought maps. I thought it was a joke that he thought it was real.
How about that? There is one thing I want to ask you about. I know it’s a professional passion. We talked about mentors. I’m assuming you would be a very coveted mentor. In particular, I know it’s critical to you that we develop the next generation of financial leaders. You’ve worked in some industries where it may be fair to say that they’ve been historically male-dominated, but I’m wondering what it’s been like for you to be a woman in those industries and how you try to pave the way for future leaders.
Every woman who’s worked in these types of industries has stories. I thankfully don’t have any that are too bad, but there have been instances where I was underwriting an investment manager in my first job, and they would come into the office for a due diligence meeting and would ask me for the coffee and ask me to photocopy their materials. They immediately assumed, because I was the woman in the room, that I was there serving a support role.
I have a deep respect for people serving in support roles. Number one, let’s make sure whenever we ask something of them that it’s polite and respectful. Number two, don’t assume that because I’m a woman, I’m there to serve. I remember in that one instance, the partner who was on the deal with me looked them in the eye and said, “This is Dorothy. She’s going to be underwriting your fund and presenting it to the investment committee.” Their attitude changed. We all have stories like that.
Not to dwell on platitudes, but I’ll tell you a story that stuck with me. I have two sisters. One of them is a sergeant in the NYPD. She is also a sociology major from Hamilton who wrote her thesis on women in male-dominated industries. When she got promoted to lieutenant, a captain in the NYPD came and gave a speech to her class. He walked up onto the stage, and they were all holding their breath, waiting to hear his words of wisdom.
He put up one word on the screen. They didn’t know what it was. It was FITFO. Everyone’s looking at it like, “What?” He’s standing there, and he goes, “FITFO. Fit To Figure It The F Out,” and then he walks off the stage. Take that attitude, have persistence, and figure it out. Don’t feel sorry for yourself. Power through, and the rewards will be there. That stuck with me because my sister manages a squad of detectives in the Bronx, and she’s doing great at it.
I’m not surprised your sister is doing great in her career path. That’s very powerful. I’m not sure that would be well-received in the world that you and I work in.
It’s very well-received. My team all knows FITFO. My whole team rallies behind FITFO. Don’t let the problem control you. You control the problem.
It makes sense. It’s funny. My old accounting brain, not that I’ve used it, was thinking First In, First Out apropos.
New accounting acronym. Figure It Out.
There you go. Apropos of nothing. First In, First Out. One thing we’ve learned is that a lot of the people who tune in to this show are Millennials. They’re people of roughly your age bracket. You’ve climbed the ladder at a bit of an accelerated pace, to say the least. I’m curious if there’s any advice you can give to the next generation of CFOs, those who see themselves getting a job as a CFO for the first time in three months to a year and a half or something like that.
I would say it’s a tough job to step into. You will have times when you doubt yourself, and it is critical in those moments not to doubt yourself. The number of times in the first couple of years in this job that I wanted to pull the red emergency cord and eject. I was in my own head space, like, “You don’t know how to solve this problem. You’re over your head on this tax structuring issue or this financial implication.” I would sleep on it. I would consult trusted advisors, and I would make a rational, informed decision. I would realize, “You can come out of that.” There were so many times when I wanted to eject because you’re going to be asking a lot of yourself. You need to not underestimate what you can do.
That’s great advice. I’m glad we were able to finally do this. This was a lot of fun. More importantly, these were some great insights for the CFOs who tune in to this show. With that, I’d like to give you the final word.
FITFO.
