What Being A CEO Taught Carol Carpenter (VMware’s CMO)

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This is a podcast episode titled, What Being A CEO Taught Carol Carpenter (VMware’s CMO). The summary for this episode is: If you want to meet a marketer who has done it all, look no further than Carol Carpenter. In her career, the Apple/Trend Micro/Google alum has been a product manager, a GM, a CEO, and not to mention, a marketing exec many times over. Now as VMware’s CMO, Carol is driving the 22-year-old software company’s digital transformation. In this episode, Carol talks to Tricia about how her non-linear career path helped her become a stronger marketer and recaps some of her biggest learnings from being a CEO. Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️⭐️ review and share the pod with your friends. You can connect with Tricia and Carol on Twitter @triciagellman @carol_carolling

Tricia Gellman: Hi everyone. I'm Tricia Gellman and I am the CMO at Drift, and you're listening to CMO Conversations. My goal with this podcast is to help you understand how to learn, and grow, to keep up with the changing world of marketing, and especially to excel in the role of a CMO. Today's guest is Carol Carpenter, the CMO of VMware. Carol's a marketer who's done it all. Seriously, in her career she's been a product manager, a GM, a CEO, and not to mention a marketing exec many times over. There's so much I want to talk to Carol about today, but let's jump into it. Carol, would you like to just add a little bit to your intro and also to the definition of how you would describe VMware?

Carol Carpenter: Sure. Yeah. I have been here at VMware about three months. It has been an exciting journey. It's an interesting time, obviously with the pandemic to be on boarding and I have to say for the most part, it's gone fairly smoothly thanks to a lot of amazing technology, including some VMware technology called Workspace One. I would tell you that before I was a general manager, I would consider myself an average marketer. There's something pretty unique that happens when you're a general manager, or a CEO, or somebody who has to actually report a number every few weeks with the commit debt stretch. You become laser focused on what really will move the needle. I like to think of myself as a holistic marketer. Somebody who thinks first about the business and the customers, and then about what are all the awesome activities we need to do to drive to have that kind of business impact. I have to admit, I think when you have a number on your back and I tell people who want to go into marketing, earlier in your career, if you have the opportunity to be in sales or in some kind of frontline customer facing role, do it because you will gain such an appreciation for what customers really need and what salespeople who, in at least B2B, what salespeople really need. I'd like to think I became a lot better about focus, what matters, and making sure that even brand activities pull through into demand programs and have impact on customers.

Tricia Gellman: Yeah, I think that's an ongoing conversation between CMOs and CROs because obviously the CRO has a number on their back every single day and you see that their careers could sometimes be very, very short because it's so measurable. I think they like to complain that maybe marketers don't really think of life in such a critical way, but I truly believe right now is a time where if you want to be at the CEO's table, if you want to be in the conversations with the boardroom, you need to think of what you're doing as being responsible for revenue. It's not okay anymore to just think of yourself as a brand marketer when you're a CMO.

Carol Carpenter: Absolutely, hundred percent. I think when you look at the marketers who are having impact, they're the ones with a seat at the table who look at the business, who think about how do I connect all of these incredible activities to business impact. I think the other part about it too, is I tell people this, we can run a lot of activities and even when I was interviewing at VMware. I said," Look, if you're looking for somebody to run up and down the stairs faster, I am not your girl. If you are looking for someone to build high- speed elevators to get to the 100th floor consistently, repeatedly, fast, that's what I do. That's what I enjoy doing, which is building the team, the processes to get us to 100th floor in a high- speed elevator."

Tricia Gellman: That's awesome. That was going to be one of my questions is, I mean, you just said you've only been at VMware for three months. I'm so grateful that you're taking the time even to meet with us today and have this conversation. I've talked to a lot of CMOs who do believe in this revenue focus and have been in their jobs for three, six, nine months. I think it's a pretty common thing is that there's a CMO turnover when there is a change in the business. Can you talk to me about what attracted you to this role and really what is the directive that you kind of have now in this role?

Carol Carpenter: Yeah, for sure. Thank you for making the time to have me. I'm delighted to be here. I should've said that earlier. This is just such a nutty time and I think the more we can help each other and share best practices, the better. For me, there were combination of things that attracted me to the role. Number one, the people. I think for a lot of us who have worked in the industry, obviously working with great people makes a big difference in day to day satisfaction. Number two, I believe, it's been proven to me since I've been here, VMware is in a really unique strategic position in the industry. I'll just double click really quickly. This leads to my remit or my mission, if you will. The company has a long history. It's a 20, 22 year old company that started with this incredible innovation called Virtualization, which for which we have hundreds of thousands of customers. Talk to any major enterprise and they use VMware in some way, shape, or form. Incredible foundation. Over time the company has grown tremendously, both organically and inorganically and now we have five franchises. There's Multicloud, we have an app modernization business that speaks to developers in DevOps. We have an end user computing business. We have a security business, which obviously affects everything and everyone all through the IT environment and we have a networking business that is kind of the underpinning for most enterprises. We're able to have these conversations now at all these different levels. The company, through its own innovations, as well as these acquisitions I mentioned, has transitioned dramatically from 100% licensed software, to in our recent public earnings announcement we announced for around 22% SaaS and subscription. That's a real shift and you and I were talking about it earlier. It's not just a shift in business models, a shift in how we go to market, how we treat our customers, how we market to them, how we nurture them, and how we recognize revenue, and sales compensation. It's major change. That is the business change that I stepped into and that frankly excites me. Coming in to be a peacetime CMO. Well, that would be no fun.

Tricia Gellman: We get a wartime, wartime CMO. I mean, we're living in this world where right now we have no sun. Then on top of it, you have a company that's going through a major transformation.

Carol Carpenter: Yeah. I did the usual. I came in first month, two months. I've been doing an extensive listening tour. Talking to everybody at all different levels to understand what are we doing well? What are we not doing so well? Where are we trying to get to? Where do we need to be? I tell people," We are the largest non- cloud cloud provider." I mean that. This is our SaaS and subscription business is all around this, which is we have partnered with every single cloud provider out there. From AWS was the first and still a preferred partner, Azure, Google Cloud, Alibaba just go down the list, IBM, et cetera. The unique strategic position is the world is a multi- cloud world.

Tricia Gellman: Yeah, that's true. crosstalk

Carol Carpenter: Large enterprises, they have applications and workloads still on- premise. They have them in clouds. They're choosing multiple clouds for different applications as well as to avoid lock- in and often-

Tricia Gellman: Mitigate risk.

Carol Carpenter: Yeah. For lots of reasons. In this multi- cloud world, where's the glue that holds it together. How are you going to, I call it all the ilities the manageability, the operability, the secureability, the observability. All the things that need to happen and that frankly is the core of VMware. This abstraction and ability through software to manage heterogeneous environments. That's what I think is pretty compelling. I spent a lot of time talking to CIO's. I've spent a lot of time talking to customers and let me tell you they struggle. They all want to move to the cloud, many have, but then how do you manage across these heterogeneous environments? That's what I'm super excited about.

Tricia Gellman: That's awesome. You're so passionate about it and I hope that in another nine months, you're just as passionate about it, but I think I mean, it's obviously a long journey. So it's not something where after three months or six months you're going to come in and then it's just going to be this transition. I do think in this world, it's challenging for people because they have to manage so many different things. The world has just changed so much in the past 10 years and it's not letting up. I mean, it just continues to change. So we all need to figure out what is this sort of overall overarching architecture that we're bringing together to kind of win and all the different parts of our business. One of the things that I think is interesting is that you have this dynamic versatile background. I would think that it helps you as you go to talk to these CIOs, all these different customers, you look at all the different technologies. What is it about your background that you think makes you uniquely positioned to kind of solve the challenges that VMware is going through with this big transformation?

Carol Carpenter: Yeah. It's such a great question. I think that, especially in technology marketing around these more complex systems, I think you have to have some affinity, some passion for the actual products and services. When I was at Google Cloud, I have been and I'm very hooked on what we're doing with machine learning, what we're doing with hybrid cloud. I think you have to care and you have to have enough interest. I think my advice to some marketers is, it's amazing to be an expert in demand gen, in content syndication, in social media, but what will really make you a superhero in these tech companies is if you can marry it with a more deep, and I'm not a programmer, but a deeper understanding of what the products actually do and the value they bring. I think for me, part of that came from my first job out of B- School was with Apple and I was a product manager. Again, like I said, I was not technically trained at all and they have an interesting model and they still have it today, which is the product manager, or product marketing manager, is both inbound and the outbound person. It's based on a belief that if you don't understand how the products work, how could you actually communicate that and express that to customers well? I just remember, I spent my first few months calling because we didn't have crosstalk is ubiquitous as they are today, calling engineering friends and saying," I need you to explain to what a motherboard actually does. I need you to explain to me ethernet and how this works." Really going hard to understand because on the inbound side, making decisions, you probably don't remember, but making decisions to drop the floppy drive was a big decision. Making the decision at Apple to go to ethernet was a big decision. If you don't understand it well enough, who was I make that decision? Then the next hour you'd be in a meeting talking about the packaging, and the pricing, and what colors, and what should the ads look like. It was forced training into making sure you fully understand the why, and the products, and then also understanding the market. I'd love to see more marketers do that and there are, there are some. There are many actual I shouldn't say, but I do think for me, that is how I've tried to differentiate a little bit. Frankly, you know how it is with these companies, tech companies, where the DNA, especially like Google and VMware. The DNA of the company is so steeped in engineering that there are only a few ways to gain credibility. You can have incredible market knowledge, you can have deep customer insight, and hopefully a little bit of product acumen. If you can marry all of that, you can influence, make change happen.

Tricia Gellman: I think that's really important because what you're basically saying is that you have to understand the stakeholders and the DNA of the company that you're in because otherwise you get pigeonholed and or you have challenge to really influence and drive change, or drive adoption, and trust with the stakeholders in those other parts of the market.

Carol Carpenter: Yes. I know you talked with a good friend of mine who I think is just amazing, Kate Bolus, at one point. She and I have talked about this idea that I'm the CMO, I'm chief marketing officer. Well, why is it chief market officer? And part of that is on us. And part of that is we need to educate the industry. We need to show up smart about the market. We need to show up smart about the customers and their customer journeys. We need to show up with a provocative and opinion. We need to show up with our opinions.

Tricia Gellman: Yeah I think you and I come from sort of similar influences in the companies that we've been in, in this idea and I love the idea you sort of portray of the product manager at Apple. For the longest time, I have been a huge believer in product marketing because I think it's hard to hire product marketing because a lot of people were product managers doing what you're saying, both sides of the coin. Then they become product marketers, which is really a little bit more focused on the outbound. I started my career doing that and I feel like you get to touch all parts of the business because you have to understand the cons on your product. You have to understand the market you're selling to. You have to understand these things to come up with the right messaging, the positioning, the differentiation. I think product marketing and CMO are two roles within marketing where you touch everything.

Carol Carpenter: Yeah. I agree. I think when you look at what you're doing too, I think that ability to have that broader experience is so critical, so critical. I'm sure that's why you're doing what you're doing too.

Tricia Gellman: Yeah and I think it's painted this picture for me, which is why I have the podcast series and why I have my newsletter. To really educate people that they should seek out this differentiated background because you want to be able to drive change. You want to be able to be strategic. In my past three roles, I've been able to work with product to define the market like you said, the Kate Bolus, who are we going after? Then if you have that definition with marketing and product of what you're doing, it makes it so much easier to then go to make your number because you're telling a story and the products are actually built to align to that story and that audience, which then helps sales. It all kind of starts to come together when you really bring these teams together.

Carol Carpenter: Everything you just said becomes 10 times more important with SaaS, crosstalk with products. Where the marketing is part of the product experience. It's so intertwined.

Tricia Gellman: Yeah. I totally agree. Well, when we spoke before you also talked about how you had this varied career with your CEO, your GM role, et cetera. It seems to me that you are willing to take a lot of risks. You weren't a CEO, but then you saw that opportunity and you said," Okay, I'm going to be a CEO. Let's see what happens here." How has that influence you as a marketer or just in general as an executive in terms of this risk tolerance?

Carol Carpenter: Yeah. It's so interesting. If you have giving me a piece of paper 15, 20 years ago, I certainly would never have expected I would have done these different things. It was more, I'm going to just share this quick story, that I had been at Trend Micro six and a half years and I was a general manager, which was the true GM role there. I had a PNL, I had sales, I had engineering, I had marketing. I had in my head, dodo bird, and I certainly mentor women to not do this. I had it in my head that I could not, and I was getting calls and pings for president, COO, even CEO of small companies, but I had it in my head that because I had not been in a startup in 10 years that I had to go to a startup, do a functional role before I could be a CEO. I wish somebody had said," Are you kidding? What are you thinking?" Anyway, I took a CMO role at a startup that was the hottest startup. Hot, hot, hot, lots of VCs, brand names, gray loft, blah, blah, blah. I was there for two years. It was a very, very rocky experience at the end because the head of sales and myself, we went to the board and said," Our CEO is great, super nice, but probably is not the person to scale the company." At which point the board brought in a COO who then became CEO. Anyway, the COO came in and he brought in his own folks. I think [crosstalk 00:18:15].

Tricia Gellman: For the company and not in the end being a good thing for you.

Carol Carpenter: We've all seen this movie, but I remember what started it is I said to a friend, I said," You know what? I feel like I know more than the CEO." She said," Well, I don't understand why you're not a CEO. Everybody has to have a first of course." I said," Yeah." I said," Well, maybe instead of working for dodo birds, I should go be the dodo bird." Then literally, which is a good friend, she said," Why don't you do this? Because you're not in a rush. Thankfully, you don't have a financial end of the road coming. Why don't you just give yourself, call it six months, a year, whatever you're comfortable with and say, every phone call I get for a CMO role, I am going to say, no, no, no. I'm actually looking for CEO roles." And she said," See what happens?" I got to tell you [ Trish 00:00:19:15], it was the strangest thing, it works. If you just [crosstalk 00:19:17].

Tricia Gellman: Put it out there. [crosstalk 00:19:18].

Carol Carpenter: Oh no, no, you can't be a CEO. What are you talking about? But literally I'd say this to every recruiter called me," You know, actually I'm really interested in CEO roles. Here are the type of companies," and they were all like," Oh yeah, okay. Well, I have these other things I'm working." It's amazing. You just have to put it out there. Anyway, make a long story short. I did end up taking the CEO of ElasticBox, which then I subsequently sold 18 months later and that's another really incredible learning experience. I did it because I thought I could be a better CEO. I thought I had enough experience. Of course, I learned a tremendous amount in the role and it's hard. It's hard. The hardest part for me was not the work, or the product market fit, or the hiring and firing. The hardest part for me was the emotional responsibility, which I think all CEOs must, I know they feel.

Tricia Gellman: Yeah. For the employees, for the future of the company, et cetera, et cetera.

Carol Carpenter: Yeah. We're at the holiday party and instead of relaxing and celebrating with the team, my husband's like," What's wrong with you?" I mean, I'm looking around at these kids, and families, and feeling this incredible weight. If we don't get to escape velocity, this is on me. That's the emotional crosstalk

Tricia Gellman: Hard.

Carol Carpenter: Yeah.

Tricia Gellman: I know crosstalk George Hugh, I worked with him at Salesforce, and when I was deciding to be a CMO and when I was leaving Salesforce to go interview for different positions, of course, I had a long history in product marketing. You had a long history in demand gen. I was talking to him and I said," Hey, you left Salesforce and you created your own company. You were growing the company. It was doing really well. You ended up selling it, but then your next role you took as the COO of Polio." He said," You know what? I just decided that not every company I could be the number two and really enjoy and be passionate about what I was doing, but that weight of being the CEO, wasn't my favorite thing." He said," You should decide. Do you want to be the number one and carry the weight of your department, of the team, et cetera? Or do you want to be the number two? And look at the things that you'll be able to achieve at a company and make that as a conscious decision."

Carol Carpenter: Yeah. Right on, 100%. Then the other piece of it too, is I think for type A folks there's this, I want that CEO title, but then you realize it's not really about the title, it's about the team. I think Trend Micro where I was a general manager was such a great experience. I learned so much. I ran this business that we grew from 150 million to almost 600 million and I've made this transition. I call it the me to we transition where it's not just about me. The success is based upon the team, not me. When you're a CEO, you realize that even more. So much so that the title doesn't matter as much. Do you know what I mean? If somebody came along with an amazing CEO opportunity, of course I'd consider it potentially, but I don't have that ambition to, I have to have a title. For me it's can I have the impact? A lot of what you were just sharing that George said.

Tricia Gellman: Yeah, I think it's really interesting, but I also think, and if you're willing to share, I'd love to hear your perspective, not just about sort of title versus team, but the loneliness at the top. I look at the CEO as such a tough role because at least in the C- suite you have your C- suite peers. When I left Salesforce to go to be a CMO, I left a team of people where I had all of these amazing VP, SVP peers that I could go to and we can brainstorm. If you think you're at the top, I mean, you're at the top. Is it lonely and also how do you kind of supplement that? Because obviously CEOs aren't up there because they just want to be by themselves.

Carol Carpenter: I put together what I call Carol's kitchen cabinet. Yeah because kind of like when I took the job at Apple and I didn't know very much about motherboards, and chips, and how computers actually work, I did the same thing. I called up four friends and I said," Okay, you were a first- time CEO at one point you're now," and it can not be your board. It can not be your execs. They have to be people who will give you hard truths and are not associated with your business at all. That was my kitchen cabinet. I went to them a lot. Like," This is what I'm seeing, did you ever see this? What did you think? What did you do?" There are a lot of more structured forums for CEOs, but I just found for myself, I was much more comfortable with four people who had known me, with whom I'd worked, who had gone through a first- time CEO experience.

Tricia Gellman: Yeah that's amazing. I even think being a CMO in some cases, it depends on how big your company is, but it can be a little bit lonely because I mean, the eye is on you to make all these decisions about the marketing. I have a idea of having what I call the personal board, which is kind of like your Carol's kitchen cabinet of just people that are outside of your company that you can ping. Two weeks ago I had somebody ping me and they said," Oh, we're going through such unprecedented times. And nobody thought that revenue would grow this way or that way back in May or June, but now it's August and everything seemed like it was going great. All of a sudden our conversion from leads, and meetings, to pipeline has fallen through the floor. Are you seeing the same thing?" I said," Yeah, it's really weird. In the last two weeks we've seen this major slowdown in this transition from holding the meeting to opening the opportunity and progressing." We talked to multiple people. A little personal board and it was like," Yep, we're seeing the same thing. It must be because people are freaking out going back to school, end at summer, it's a really busy time for distraction. We should just see what happens get into September." Now, it's all back on the up and the up, but it was really valuable to have that group of people to just ping that idea out and see what was happening.

Carol Carpenter: Yeah. Good for you. Good for you. I mean, we have VMworld coming into weeks and for sure, virtual events at scale, this is all new territory for so many of us. I've been pinging a lot of industry friends to say," Okay, what are you seeing? Did you see that last minute registration and what level of engagement and what tips and tricks do you have?" So for sure.

Tricia Gellman: Hey, everyone. Molly here from Drifts Podcast Team. This is where we're ending today's episode, but don't worry we'll be back next time with part two. Where Carol shares, how her experience as a CEO and GM helped her become a stronger marketer. Before you go, make sure you're subscribed to the feed wherever you're listening from. It's the number one way to make sure you don't miss an episode. If you really liked this episode, please be sure to leave us a six star review wherever you listen to podcasts. If you're looking for even more CMO content, we've got a newsletter for you. Once a month, Tricia shares the customer centric, data- driven, and barrier breaking marketing headlines that are defining today's CMO. Sign up at drift. com/ cheap- marketing- officer.


If you want to meet a marketer who has done it all, look no further than Carol Carpenter. In her career, the Apple/Trend Micro/Google alum has been a product manager, a GM, a CEO, and not to mention, a marketing exec many times over. Now as VMware’s CMO, Carol is driving the 22-year-old software company’s digital transformation. In this episode, Carol talks to Tricia about how her non-linear career path helped her become a stronger marketer and recaps some of her biggest learnings from being a CEO. Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️⭐️ review and share the pod with your friends. You can connect with Tricia and Carol on Twitter @triciagellman @carol_carolling