When it comes to preventing attacks, “every second counts in the cloud.” That high-speed, high-stakes work is part of what drew Karen Walker to start her career in Silicon Valley, and eventually take on her current role as CFO of cloud security company Sysdig.
Walker joins Jack McCullough to share her journey from global childhood experiences to leadership roles at iconic companies such as Uber and Pandora. Together, they explore the evolving role of CFOs, the power of networking and how technology is reshaping financial leadership.
Listen by clicking below. The Q&A, lightly trimmed and edited for clarity, follows.
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Listen to the podcast here
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We have a great guest again today. Karen Walker is the CFO of Sysdig, a high-flying company in Silicon Valley, in the cyber tech security space. Karen, welcome to the Secrets of Rockstar CFOs.
Thanks for having me. It’s a pleasure to be here.
It’s great to have you. Sysdig is one of those companies that is not 100 percent name recognition yet, but something tells me that in about two or three years, it’ll be pretty close to that with my audience. What can you tell us from the 10,000-foot view about Sysdig?
We are in an exciting space that is in its infancy with multiple decades of growth ahead of us. We are a cloud security company. We secure software applications that are built in the cloud and for the cloud. It’s core infrastructure cybersecurity things that you may not think about in the day-to-day as you go through your activities. Things that consumers do in this digital world like online banking, booking travel or doing rideshare are things that are secured by our platform.
Our mission is to be the leader in real-time security, which is so important in the cloud because attacks are happening faster than ever. Especially with the advent of gen AI, the attack surface is getting broader as well. Responding to attacks and preventing attacks in the cloud is a matter of minutes. We like to say that every second counts in the cloud. We’re the only platform that not only helps with prevention but also detection, so being able to understand as fast as things move in the cloud and the level of automation, understanding user activity to prevent attacks before they can happen. It’s an exciting space. I’ve been here for almost three years and there’s never a dull moment.
It’s an exciting space to be in. It’s fantastic. I’d love for you to share a little about your early years. Where did you grow up, Karen?
I grew up in a bunch of different places. My dad was in the military. I am often called the Army brat or military brat. It’s interesting because it has formed a lot of who I am today, with the reality of moving quite a bit as a kid. I was born in New Jersey. I lived in places like Panama, Italy, Texas and Arizona. I made my journey out to the Bay Area as a young professional. Not everybody always picks up from where they last lived or where they grew up. I grew up in so many different places and had a big interest in being able to see new and different things.
That’s a fantastic experience. I don’t have that thing. I lived in the same house my entire life until I graduated from college and even then for several months after that. It’s always interesting to me when people have that global childhood experience. You studied business as an undergrad. Is that correct?
I did.
Choosing A Career In Business And Finance
When you were 17 or 18 years old, what was it about business and finance that you found compelling? You made a great choice.
Yeah, I made a good choice. It’s interesting because I wanted to veer a little bit more towards the finance degree. I got my degree in accounting, but one of the other things I would say about my upbringing and my parents, they were born and raised in New York. My dad was in the military as I described. He was a soldier, so he was a non-commissioned officer. My mom did work sometimes while we were growing up, but she also mainly raised her kids.
They were born to immigrant parents. They had some college but neither one of them got a four-year degree. Some of those options weren’t available for them given their socioeconomic status growing up. I’m one of three and it was important to them for their kids to go to college. They were very focused on that. They were also thinking ahead to what will provide stability as a good path where you’ll always have a job.
When I started taking some of the accounting coursework and then was thinking about flipping it over to broader finance, they were very concerned. They were like, “You’ll always have a job in accounting.” I started down the route of public accounting, but I hear the story so often, the one that I’m describing. A lot of times, as all parents do, they want to make sure that their kids can do better, succeed and be better off. A lot of times, that can be more of this practical route versus the big dreams.
I was the same way with you. I didn’t have lofty dreams to become a greater thinker or have a greater understanding of the world. I went to college simply to get a better job than I would have been able to get without it. That’s why I studied accounting. I graduated college almost 40 years ago. As an accountant, I wasn’t even that good at it, I’ve never been unemployed in the course of my career. It is one of those careers. If you’re into stability and want a nice career, it’s certainly a great place to go. It can be very lucrative too if you’re at the top of the game so to speak.
The other interesting thing in this may be more of a generational thing, but also maybe part of my parents’ background. They were very much thinking about a job. They use the terms job versus career. In the early stages, I had that view as well of stability and then this is the job, and to not even dream big in the field that I was in.
Moving out to the Bay Area and moving out to Silicon Valley changed that for me. I started out working in public accounting and serving a number of different clients. First, it was in real estate and then I said, “I’m here in the Bay Area, in Silicon Valley, let me explore technology companies.” Real estate companies versus technology companies could not have been more different worlds. In real estate, it was like you had a job. There’s a packing order and it’s very hierarchical.
When I started to get exposure to some of these technology companies, everybody had equity. They have ownership. There’s this emphasis on innovation. You can have new ideas and you can be more adventurous. That was something that sparked my interest. I made my way very quickly out of public accounting as soon as I could to join one of these companies. It completely changed my trajectory and the way I thought about having passion and inspiration for this is a career and not necessarily a job.
That’s an interesting observation. You may not know this, but when Silicon Valley was first coming into its own, a lot of the people on the East Coast were the ones with the money. Because employees had ownership of the company, they thought Silicon Valley was trying to turn the United States into a socialist enclave.
That’s so fascinating.
You didn’t think that was true, did you? It didn’t occur to them that having an ownership stake in the business, an entrepreneurial mindset and the freedom to do some things differently.
Engage in innovation and do the right thing because we’re all on equal footing in the sense that we’re invested in it.
Career Highlights: From Uber To Pandora
Yeah, the old-school money people of that era. We’re going way back when Hewlett-Packard started, and a few other companies. They couldn’t have been more wrong, I would think it’s fair to say, with what we now know all these years later. One thing about your career path that’s intriguing is you’ve worked for some of the best-known, iconic companies in the tech space. You’ve worked for CBS Interactive. That’s not necessarily tech, but Virgin America, Uber, Pandora and PagerDuty. Walk us through that path a little bit. What are some of the big lessons you’ve learned, maybe some momentous thing you’ve had along the way?
I’m happy to elaborate. The first big lesson for me is that people always think about finance and accounting as this portable skill, and it is. You can apply how to close the books and how to forecast into a lot of different industries. I will say that I look at my experience of chunks of consumer businesses, new media, marketplace with Uber and now enterprise software, and even a small foray into airlines, which was fascinating, a very complex business.
I appreciate the breadth of experiences and how that can make you stronger. One important thread is to have a very deeply vested interest in the business. You can certainly exceed and do your job well in finance and accounting without that. What’s going to separate you and make you excellent is this interest in the business because that’s when you can take being at the center of all of this data, information and insights, and work with operators to make smarter decisions about how you allocate capital, how you support the strategy and how you help the business execute.
When you’re passionate, that’s when you turn on those insights versus just doing something because you’re like, “I have this portable skill. I will just go and work where I’m not passionate about the industry.” That is the first thing that I would say. The second thing I would say is being able to not only take collective different experiences across Industries to grow, but also different stages of companies. If I look at my experience, for me, the sweet spot is always about growth and scaling.
I enjoy the ability to do that, but I’ve also worked at companies that were already public and very mature, like Pandora Media. It was $1.5 billion when I joined. It had some interesting challenges that were different than something like Uber. When I joined, there were less than 500 people, about $100 million of revenue, and then from my time there, growing to over $2 billion, and over 10,000 employees. It was a very unique experience. The breadth of not only different industries but different stages of companies can make you a strong leader and lend Itself to a good career trajectory.
Those are the those are two things. The third thing I would say is to take what I said at the beginning about what you’re passionate about and seek out some of the opportunities versus waiting for them to come to you and make your own luck. I’ll use two examples there. With Uber, I became super interested in Uber right around the time that they raised their series C. Google Ventures led that round. I would have already been using the service and I thought it was fantastic. I loved it. It was a real game-changer. Even though I lived in San Francisco, I lived in a neighborhood that was a little bit more remote where I’ve had been refused [cab] service to the neighborhood.
Is that legal?
I did get bounced by a guy going downtown. I was very upset and I agreed to get out of the car because it was not a good experience. Starting with that point of “I’m passionate about this. The service is great,” to saying, “This seems interesting.” They just raised money. At that time, with Google Ventures leading, I thought, “This is the path to partnership to autonomous vehicles.” I could see that long-term vision at that time.
I started checking out who in leadership was there, and how was I connected to them. I found my way through my network to get connected to them. It was very fortuitous because they were about to launch the role that I ended up landing, but it was something that gave me a little bit more of an edge. At the time, I remember networking with another colleague who had a great similar experience and also applied for the role.
The Importance Of Passion And Networking
They told me when I got to the final stages of my offer that more than 100 people had applied for the role. This is back in 2013. I would argue they only continued to become more visible as a company thereafter. It’s this thing about creating your own advantages and your edge to get in there. It is so important. The other thing I would say on the network, too, is that you always have to be thinking about nurturing your network and not just reaching out to people when you need something. How can you help them, but also how can you check in?
Even if it’s telling people, “Here’s my progress update. Here’s where I’m at.” I did this when I joined. This became a critical piece for me when I joined PagerDuty because I had networked with somebody who joined their board. She was a sitting CFO. I talked with her about coming to her company. It didn’t quite work out. It wasn’t the right time for me. Instead, I went to Pandora Media, then we sold the business to Sirius XM. My role was eliminated and a lot of G&A roles are eliminated when that consolidation happens.
I started to do some outreach and started to have some copies. This person who is the CFO was on my list, and then I rattled off. She knew I wanted to get to the CFO seat and started talking about supporting investor relations. I later led investor relations at PagerDuty but supported investor relations. I did a lot of work on the capital structure with a more sophisticated treasury. She said, “I want to introduce you to this company because there’s a unique role that they are looking to fill. That’s where I became the SVP of finance, overseeing FP&A and accounting. I was the first person to lead and build their investor relations function. It’s a lot about networking and taking some risks, leaning in and going after what you want.
I have a colleague. I don’t know if she invented the phrase, but she always says, “Your network is your net worth.” You seem to be living proof of that. Your contact at PagerDuty, was it Elena?
It was, yes.
This is the 30th episode we’ve had and you are the third person who mentioned she helped them find a job or something. Does she look like every single person in Silicon Valley? She’s great. She keynoted our conference a few weeks ago. To no surprise, she nailed it. As soon as you said a female CFO, I know there are plenty of them in Silicon Valley but I’m like, “I’m pretty sure Elena was on the board of PagerDuty at one point along the line.“
I have to ask you because you’ve been involved in two of the most visible exits in the last several years with Uber’s IPO and then Pandora being sold to Sirius. I love to get your take. What was that like? How is prepping a company to go public the same and how is it different? I don’t even know if you were attempting to get sold when you were in Pandora. What are some of the differences in how that worked out and what are the valuable lessons you learned?
I’ll start with Uber. It was so interesting. I joined that company and it was not your typical series C company. We were already in about 17 countries and growing so fast. We measured our growth month over month. If you think about that now, it’s astonishing. Most software companies right now are growing between 10 percent and 15 percent a year. We were growing 15 percent to 20 percent a month. It was pretty insane. Similar to a lot of venture-backed companies, finance is not the first immediate thing that they invest in.
There’s a massive amount of catching up to do and cleanup that you need to do. Imagine you’re trying to do that in a company that’s already still growing 15 percent to 20 percent each month, and then add on to that, during the time I was there, it was a massive expansion in the ride-sharing category, but then also entering things like the food delivery space with Uber Eats, some experimentation as well with an autonomous vehicle. Investments are being made there. To me, it’s the paramount once-in-a-lifetime experience of scaling. For me, there will not be another experience like that.
Probably not.
I guess a huge takeaway that is important from that experience was you need to be very thoughtful about hiring quickly but hiring the right people. We had an interesting paradigm. I didn’t create it but I adopted it and made sure we carried this throughout. We didn’t go through eight long interviews or a big interview cycle. We made it like what’s the critical path and who needs to be involved, and then there would always be some test or exercise to understand this person. We tried to build those that were realistic, something that we would be dealing with.
It was such a great way to screen through and better understand whether somebody will be successful here or whether it is a good fit. That was one of the key things because as I said there were a lot of things to do and fix. I started with such a small team of less than 10 people and then built a team globally of more than 70 people around the world. That was key.
What period of time was that when you grow from 10 to 70?
I was there from 2013 through 2016.
By any reasonable standard, that’s fast.
It’s fast. Think about systems and things like that. It was crazy. Believe it or not, we were on QuickBooks. There was another ERP for the international. In the beginning, we were not able to consolidate all of our results. We did a very rapid implementation of an ERP in about seven months and spent a fraction of the cost that people spend on these projects. At that time, we were not able to go into the cloud because the business was so complex, with so many currencies and so many legal entities, and a lot of those offerings were still very nascent.
When you think about it, companies that were doing these types of projects could spend 18 months to years and spend millions of dollars. We did it in seven months. The people I worked with and the teams, everybody was amazing and the level of commitment was off the charts. The thing I would say when you’re growing that fast, the business does a lot of experimentation and innovation and starts to look at nuances of business, but also sometimes new offerings, like UberPool was a carpooling service. The pandemic probably killed that. I’m not sure if it’s back yet or not, or if ever came back.
There were all kinds of different pricing experiments and different things that were happening. Even as you build and you scale the team and you get better systems, the reality is that you can’t respond to every single thing. You have to understand the 80/20 rule and understand, “Is this experiment not bigger than a bread box? Do we need to let it go a little bit before we invest to scale and build around it?” That was pretty unique at that time.
The last thing I would say is about IPO readiness. I was involved in very early IPO readiness there. Given the complexity of the business, I was starting to think through, what are the key metrics? Do the businesses have segments? How do we think about parts of the business that are already profitable versus areas that are more emerging growth? It was fantastic. It was a great experience.
When I think about about Pandora and the sale to Sirus XM, this is already when I joined the company with about $1.5 billion of revenue, but a lot of things that Pandora was focused around is making it a healthier business. A lot of things around the music licensing contracts, making those, structuring those in a way that was more advantageous than the deals that were originally struck, and then working on capital structure. It was a very complex capital structure that we had, so working on how to shore up the balance sheet for the investment that was needed.
I had the unique opportunity to work with a great CFO. When I joined the company, I was like, “I want to become a CFO.” I’ve gotten all this great experience and that person let me in to work with the investor relations team to help support the team during the earnings process. It was such a valuable experience. We had so many analysts who covered us. We dual-tracked. We would start the day on earnings with the CEO and the CFO in the same room. We would listen to those callbacks, and then we would break off and divide into two smaller teams.
This is another piece of advice that I give to people. You don’t have to necessarily own or be the owner of that function or run the function to get deep knowledge into the function. That’s what happened to me in investor relations at Pandora because I worked with a great IR leader and a strong CFO. When you’re in the room even and listening, you just learn a lot. That’s one of the things that helped me when I was at PagerDuty, to be able to be the person that stood up that function. It was all of the learnings that I got from being in the room. It was fantastic.
That makes sense. It’s interesting that you worked in investor relations before becoming a CFO. Not that it’s unprecedented, but I don’t hear a lot of that very often. Do you think that someday it will be recognized as a more viable way to get to the CFO role? In my generation, it was public accounting, comptroller and CFO. I just described 97 percent of the CFOs of my age bracket as an exaggeration. Do you get my point?
In the last decade, there has been a complete shift. There were more bankers becoming CFOs even though they didn’t necessarily have operational experience, or sometimes people even from a strategy background. Here are two thoughts that I have on it. First of all, I would say in today’s environment with a focus on profitability, the CFOs who have more operational experience and can sharpen the pencil around that path to profitability and that focus are going to be in the band for some time.
I don’t think that cycle is ending. That’s one thing. The other thing, I might have this bias because it reflects my own background, but getting a broad set of experience is so valuable. I think about it and I didn’t necessarily have a straight and narrow path. I was in P&A early on in my career and I ventured more into the comptroller and accounting side.
I had a lot of recruiters tell me, “You can’t become a CFO because you’re typecast now into this,” even though I had FP&A experience earlier on. I didn’t listen to those people. I leveraged my network bit by bit to take on these other pieces and it worked for me, but it helped me become more well-rounded. Especially if you’re a public company CFO, you’re not going to own all of those different functions, but when you’ve had a deeper insight into them, you’re going to hire better as well and know what you need.
The Relationship Between CFOs And CEOs
That makes all the sense in the world. I’d love to chat a little bit about Sysdig. What motivated you? What was the attraction to stick when you decided to join?
There are a couple of things. One thing I would say is a strong relationship with the CEO, which the CEO and CFO have to have a tight relationship. The second was the mission of the company and what it was doing. The third thing was the culture. That’s so so important. First off, when I met our CEO, Suresh Vasudevan, I hit it off with him. The common thread is when he was explaining to me the business and the problem that Sysdig solves. The narrative of what drives the growth at Sysdig and the tailwinds like cloud adoption and digital transformation are all things that were secular tailwinds in the PagerDuty story as well.
We have this immediate connection of talking about, “I get that.” I understand what’s driving the growth and what the narrative is. Also, Suresh was looking for somebody who could be more publicly facing. He was already thinking ahead about that industrial relationship or aspect and how you tell the story. That was an area that we connected. I appreciated the fact too that he has great life experience. He’s also been there and done that, too. He has been a CEO a couple of times before. He has taken a company public and sold the company. That’s something that I found reassuring and also somebody that I could learn from. That connection was foundational for me in terms of making the decision.
The second thing is the opportunity which I hit on a little bit. I like to be part of companies that are disruptive. Sysdig is disruptive in that regard. When you think about all of these legacy vendors that now are trying to come and pick up into the cloud security space either through acquisition or building out some of their tools. When you think about this transition into the cloud, the adoption of microservices to build applications more quickly, and the scalability of the infrastructure behind the cloud, we’re in the very early phases of this.
There are customers that we have that are born in the cloud and are cloud-native at the start, but then there are a lot of companies or customers of ours that are just getting there. They’re early in their journey. There are tons of growth and what we’re doing being purpose-built for the cloud is unique. I love what I described earlier about how we’re doing it and how we’re different.
That was key, and then I got to meet a lot of people on the board, as well as more importantly, some of the other executives. Not everybody, but a few of those people had worked with Suresh before. That spoke a lot to his leadership. They talked very candidly about what they liked about our culture, that we were customer-focused and that we dig in but in a collaborative environment. Those were the things that sold me.
That would sell about anybody. That sounds like a compelling case. I’m glad that you brought up Suresh because my next question is going to be about the relationship between the two of you. The most common question I get asked by first-time CFOs is, how do you build that relationship with the CEO? It sounds like you guys have a great relationship. On the other hand, it almost seems like you had a great relationship wherever you go. It doesn’t sound like you had to work to develop a great relationship, but I’m sure you’ve got your challenges and disagreements. How do you continue to build upon a great start?
You’re right, the foundation is making sure it is a fit and that you can test the boundaries of that, understanding also, “What do you want in a CFO? What are you looking for? Where are the areas that you are looking for more support and partnership?” That’s super important. Anybody who’s on the executive team or anyone who’s reporting to the CEO should be able to also bring in some expertise beyond just their functional domain. That’s very important.
A lot of people have said this. I don’t think I’m saying anything new here, but the remit of the CFO is broader than ever before. People don’t view it as that back office, tell me what happened, the compliance, the forecasting and all of that. It’s like driving insights and being a partner to the CEO, and the rest of the executive staff on how we can build a strong business. Sometimes that means being comfortable for all the executives with not always agreeing. If we both agree every single day, one of us doesn’t need to come to work. It’s having that comfort level.
That makes a lot of sense. The CFO role is unique because you’re probably the only person on the leadership team, unless you’re in that company where the CEO is a former CFO, with the strategic vision in the financial expertise. In your role as CFO, how do you blend those two and make sure that finance is supporting the company’s overall strategic objectives?
It starts with a deep understanding of the product and the problem that you solve. It’s about getting out into the field. For example, I will have my one-on-ones with the leaders of our APJ region, and the sales leader there. You are digging in and understanding what you are hearing in the field, understanding all of the different aspects of it, not just being a person who’s modeling or behind the numbers or hearing it filtered through other people. I feel like that’s one super important area. It is to make sure that you’re taking the time to dig in and understand those different areas.
That makes a lot of sense. Sometimes finance isn’t necessarily as well-thought-of across a company as some other aspects like an engineering firm where it is still marketing driven. How do you collaborate as the leader of the finance and accounting team cross-functionally, and make sure they understand, “We’re not just reporting things after they happen. We’re driving genuine value here.”
For starters, one of the things I like to do is set the tone with my own team of being customer-focused and having them embrace the fact that they’re here to serve the business but also ultimately, to serve our customers. If they can be very focused on what’s best for the customer, then we’re going to succeed. I like to drive things across like the goods to cash cycle. Let’s explore and examine this in partnership with our sales, ops team, and field team. Are these things that we’re doing introducing friction? Do we have friction in terms of our terms?
Maybe we don’t have the most competitive terms, or maybe we think about we have this approval process, but if we’re always saying yes, do we need to change something? How are we helping with deal velocity, and being on the front end of all of these things? Even just the services that are consumed by other employees that finance supports. When you think about even basic things like expense reports and travel generally. How can we make that equity platform?
All of these different payrolls and all of these different services should be designed around efficiency for the business. Providing good service. Make it seamless for the business. Those are the things that I tried to instill in the team. It helps because they have a broader view and they take more pride. They get good feedback from their teams. Some people even remarked, “This is the best finance team that I worked with that is focused on helping us move deals faster and helping us execute what we need to do.”
How Technology Is Changing Financial Leadership
That’s fantastic. I’m going to ask what for you will be a relatively easy question, I would think. Some of the CFOs that I’ve interviewed before don’t have your background. How do you see tech and the digital revolution fundamentally changing the nature of financial leadership?
It’s so interesting. That is such an interesting question. Very early, I’ve seen a big change even in the time that I’ve been working. Gen AI is the new hot topic for finance. A lot of finance leaders right now are a little bit leery. There’s a lot of caution. There’s a difference between predictive analytics, which are embedded in a lot of products today, and then gen AI for finance and modeling. There is a lot of discussion about whether these jobs go away or do they change fundamentally.
It’s very early days. For every business and every finance leader, it doesn’t even matter what function you’re in. You have to be dipping your toe in the water and looking at some of these new technologies and how they can drive productivity. For finance, in particular, I think people will become more comfortable with the adoption of the technology. It’ll be like running things in parallel, but also shifting and changing the work mostly in positive ways.
This is a decades-long progress. When you think about things that people used to do manually like OCR technology. You used to have to manually input this invoice for payment. Now, it scans and I don’t have to touch it. Nobody is unhappy about that. There’s a correlation between reducing the types of work that people don’t find interesting to things that are going to be more interesting. That’s the overall evolution that I see.
Even today, putting gen AI aside, I will tell you that it’s important as a leader that you take a lot of the experiences that you have in pattern recognition to identify and resolve issues quickly and make decisions about technology that you use or a process that you’re going to follow. It’s also equally important to not be so locked into those because you have to recognize that technology changes very quickly and you need to be almost constantly reinventing yourself and your team, and thinking about how you can do it differently.
This is a simple example but Google Docs is a perfect example. Fifteen years ago, a lot of companies were not using them, like to share drive, somebody downloaded something, and then he had to upload it. The fact that you can be collaborative and work on something at the same time is something that seems so obvious and easy. I would say 15 years ago, not as many people used that.
It wasn’t obvious at all. When I went to grad school, there was a product called Lotus Notes. I don’t know if anybody knows Lotus. Some people said, “This isn’t going to work.” People don’t collaborate that way. Having had my career in finance and accounting and naturally erring on the side of privacy and data protection, I had at the time legitimate reservations about embracing the technology. All these years later, I look back and think I was wrong about that.
When you think about it, it’s a little surprising some of the reservations around gen AI because you can put training wheels on it and make it safe through experimentation. To do nothing or to be like, “I’ve always done it this way.”
Go back to the ‘70s. Erik Brynjolfsson, human-centric AI at Stanford, made a comment that AI will not replace CFOs, but CFOs who embrace AI will replace those who do not.
I heard that comment. It’s spot on.
Who will argue with him? I want to chat a little bit about, not only from a technological standpoint, but how you see the role of the CFO or even financial leadership itself changing as things progress. I would say technology is a big part of that. Are there any other areas where the nature of the rule is going to change?
The CFO role has already evolved to being a more forward-thinking partner to the business and a team that should drive insights. One thing I would say that we didn’t hit on is that the CFO can partner with the business on some of the other technology gains for their functions. To give an example, very recently, we made an investment in technology for our support team to help them resolve cases more quickly. By reducing the time to resolve, they’re able to handle more caseloads. There are productivity gains there. Before we made this investment, I worked with the leader to build out this model for the ROI, like the investment that we were making.
As we progress with technology and things change, particularly with gen AI, there will be a lot of fits and starts. There are a lot of things out there anyway, a lot of tools. You could almost have people loading up on tools and then somebody waking up the next day and going, “Wait. I thought we were going to get X, Y and Z out of this.” I feel like, in many ways, the CFO could be a partner to the business on these broader aspects and in some cases, areas that have much greater impact because of their size.
When you think about something like the go-to-market function, for example, I call that tech support, but also if you think about outbound calls and things like that, inside sales reps make, the amount of productivity that could be unlocked from that. It’s usually a larger portion of the business and say the finance team and the CFO can be a thought partner in guiding teams.
Balancing Work And Life As A CFO
That’s a great answer. I always ask a couple more questions and I always like to ask CFOs how they do the work-life balance thing. I’ve been a CFO for a long time. I know it can be an all-consuming job, not just the number of hours, but it’s not the type of job where you can just click a button and turn it off and go back home. How do you do it? You’re working for one of the fastest-growing companies in Silicon Valley, building something great for the long term, but you can’t work 150 hours a week either.
I try to think about things as sprints. You’re right. There are always things to do and I have gotten into those ruts where I continue through the weekend or late into the evening, or I’m shutting down the laptop and then trying to go to sleep, which is a lot of people would recommend that’s not the right path. I try to think about it as sprints. I’ve got some big deliverables and things coming up. Those would be the times maybe that we’re all going all out.
If things come up that are unforeseen, then it’s recognizing that I don’t need to get these things done today. Let me see if I can do something outside of work. Quite often, you recharge your batteries that way as well. When it comes to vacations, you’re always going to be on in the sunset. I get peace of mind if I can mostly say, “I’m going to handle this first thing in the morning. I’m going to check in on things and things are going well. If something happens, I’m reachable and people know that,” you come back much more recharged and in a much better place. That’s important.
I often hear this from not just CFOs but other leaders where they have a hobby. They have something they like or something they’re passionate about but they say, “I’m too busy and I’ll do that when I retire.” You can’t do that. You have to make the time. If you’re passionate about something, you never know what’s going to happen. Why would you put it off? For me, some of those things are around giving back to the community and being part of the community.
I work with the ALS network. I have a personal connection and I lost my mom to ALS. I have been dedicated to that organization for the last 11 years in a variety of ways. I served on the board for six years. Most notably, the one event that I’ve committed to over the last 11 years is this bike ride that’s done here in Napa Valley. It’s quite a celebration. It’s an amazing event. It’s inspiring.
I’ve gotten to know other people right here in my community who are impacted by this disease. Giving yourself the opportunity to do something very meaningful for you can be a great way to feel less stressed and to provide a little bit of that tension of something else competing for your time, and then you find out that it’s okay. Otherwise, you’re just going to go, go, go.
That makes all the sense. I’m sorry you lost your mother that way. I understand that’s difficult for families to deal with relatives they lost. It’s great that you’re able to take that and turn it into something positive. I’m curious, how long is the bike ride?
We have something for everybody. That is what we like to say. There are six different routes. There’s a 100-mile route. There are two metric sentries. One has a decent amount of climbing. The other one is pretty flat. We have a 47-mile, a 28-mile, and then we have a family ride that is like 9 miles that people will take their young children on.
Advice For Future CFOs
That’s a great cause, so kudos to you for supporting that. The other question I always like to close with is what’s your advice for the next generation of CFOs? I feel funny asking you that because I look at you and you are the next generation of CFOs. The ones coming after you a little bit, those who are maybe about to get their first CFO job or they’re rookies. Any advice you can share with them?
There are four things that I would highlight for those. I mentioned a few of them along the way as I talked about some of my experiences. I strongly believe that you should work in an industry that you’re passionate about. You don’t want to be the best finance professional. You want to be more excited and more engaged in the business and better able to serve the business.
The second one is about getting a broad set of experiences. That could be different Industries. This can still be in technology if technology is where you want to be. You can do something on the consumer side or the enterprise side, and then get different experiences at different stages of a company. That’s so valuable and I feel like that’s something people have told me that resonates with them. There are businesses that have grown rapidly and then some businesses that need some restructuring or refinement as well.
Those collective experiences and a broad set of experiences are really important. The third thing that we talked about when we talked about gen AI and technology is that you become the expert and you’ll have pattern recognition. Don’t be so set in your ways of like, “I’ve done it like this all the time.” Be challenging yourself even if it’s not technology. Is there a better way to do it? You have to have that competitive edge.
The fourth thing is something we didn’t hit on earlier, but I believe in it. I guess we touched lightly on when we talked about Elena. Getting sponsorship is so important, especially when you start to get to this level like maybe you’re one step away from the CFO role. You need to have people, whether it’s a board member or another sitting CFO. You need that extra help to tell you the things that you don’t know, to be somebody who can say, “I learned about this opportunity.” Don’t be afraid to ask. It goes a long way to get sponsorship.
That’s great advice. Karen, this has been a great conversation. I know you’ve got a lot going on. I appreciate you taking the time out. With that said, I want to give you the final word.
Do things that you’re passionate about, go hard, be fearless, and don’t be afraid of making mistakes. You learn so much from those. You need to take some risks. That’s the way you can have a more enriching career over the long haul.
