TOP CMO: Diana Massaro, Skyhigh Security - 'Fearless Potential'

Diana Massaro  0:00  

sort of jokingly but not really saying the best way to build brand is to have a lot of passionate customers.

Ben Kaplan  0:08  

This is the podcast where we go around the globe to interview marketing leaders from the world's biggest brands, fastest growing companies and most disruptive startups. Ideas a certain way want us brand new want to be told us someone else's simple, surprising and significant data. Locking viral creativity is to make it rapidly scalable. This is top cmo with me and Kaplan. Today I'm speaking with Diana Massaro, product focus CMO of sky high security, which enables a company's remote workforce while simultaneously addressing cloud web data and networks needs. Diana previously served as CMO of armor, cybersecurity, and CEO of Piaggio software, where she grew the company with its private equity partners to prepare it for an eventual sale. For her latest role, Diana faced a unique challenge combined the acquisition of a company sky high networks with an existing security service business, McAfee enterprise to form a new entity, sky high security. Diana started three weeks after the launch, throwing her headfirst into the deep end of building out and rebranding a new business and team from the ground up to what challenges does a CMO face when starting a new? Let's find out what Diana Massaro. What I like about your job as it's new, because the sky high security comes out of McAfee enterprise IT split off from it. You have mature clients stable business, but yet you're new at the same time, you're assembling you're building a team, you have a lot of challenges at once. So talk about the challenge you face. Now both the challenge and the opportunity to do that,

Diana Massaro  1:56  

I have to go back just a little bit and tell you that I've only been at Sky High Security for four months. So I started at Sky High Security, right when we were launching our brands. So we are what they call a carve out from McAfee. So we are the cloud security business of what McAfee enterprise was. So now we are separate as sky high security. And I started and three weeks later, we launched our brand. So it was absolutely a crazy three weeks of trying, when I started, we didn't have a logo, we didn't have website, we didn't have an intranet, like we were but we didn't have messaging, we were going fast. So that was first of all, just starting as a as a CMO that was a very unique challenge. In that from day one, I started working like 15 hour days it was it was crazy and really, really fun. And so now I'm in the place where I need to build a team, we need to get really get our messaging solid. But we're also we have we have several 1000 customers are global, and we've got regular product releases. And so we have to keep sort of the trains running on time, while we're also building a new company and new infrastructure and processes. And so I like to say this is my dream job that I get to come in and build a team and a company and a brand from scratch. But it already has, like 15 years of history and product market fit and, and passionate customers. And so it's a it's a it's a fun, hard, interesting challenge for me as the CMO,

Ben Kaplan  3:41  

how do you message both at the same time listening to you talk, you said we're stable, we're mature, we're in cybersecurity, so you got to be able to trust you. But we're new and different, and maybe a better version of what you've seen before at the same time. So how do you think about that message that and I know you're a proponent of focusing on the product, not just the brand? The answer

Diana Massaro  4:03  

is it depends. So I don't always like to say that we came out of McAfee. It's important, I think to understand the CMO challenge. So I think it's appropriate for this for this podcast. But there are prospects and customers out there who have not had a great experience with McAfee. And so if you say that, then they go who I don't know. And then there's others say, Oh, that's great. That's a big company. That means that I that I trust you. So we're trying to get this balance of saying, We've been in business for 15 years. These are mature, mature products, but because we separated, we now get to move faster. We need to get in focus more on innovation. We get to really move quicker when when we see changes in the market or feedback from the market or customer issues frankly, and so try it Uh, to balance on, you can trust us. And we're new and innovative, and you're gonna see, like great new things from us.

Ben Kaplan  5:11  

There's this notion of kind of the romantic view of like, the tech company is like the garage, right, the originator, that's kind of the lore of it originates garage. But now you're in kind of a big garage, right? You have like a lot of resources you have, like you said, product releases. So how does thinking about the product, not just the brand influence how you approach marketing now, because a lot of people, they're starting something new, the first thing they do is Bradley said, like, where are we rooting this brand? What are our pillars? What are the pain points of our customers? How do we solve that, you pay attention to all of that, but you actually say, Don't forget about the products, even while you're, you know, thinking about your overall brand, sort of

Diana Massaro  5:52  

jokingly, but not really say the best way to build brand is to have a lot of passionate customers. So I don't think there's a huge, huge divide between demand generation and brand building. So we had to do some, some brand building because we were launching a new company called Sky High security that that didn't exist before. But really, the best way to get your message out there is is to understand what value you bring, and who hears about that and what problems they have. So I started my career, my first 15 years was in product management. I actually have a master's in statistics, like I'm a, I say that I'm like a math geek in a in a well adjusted marketing, like persona. Product Management, which meant that I cared, I cared deeply about who the user was and what they needed from from our products and what problems we were solving and trying to match those two together. And so we bring that into the CMO and the marketing role. And so I always like to start with, what's the problem out there. And so the problem for for our customers is, a bunch of data is moving to the cloud. And all the old security tools they had when it was on premise where you just put a firewall around it, and then you could just access everything that don't work anymore. And COVID like, slammed that so fast into these poor security and IT people who suddenly had to figure out how do I enable everyone to work from home and put data in the cloud? And by the cloud? I mean, just, you know, office 365, Salesforce, I mean, OneDrive, whatever, like and how do you make sure that you still have security and you're not putting you don't have crazy marketing people, you know, putting a roadmap out on a on an insecure, insecure SAS app, not gonna say one, because they're all there, you know, a lot of security, whether that's intention, you know, probably unintentional. So that's a problem that we solve for our customers. And so I always make my teams, my marketing teams, and some of them hate me for this, especially when they're listening to this, and make them give me the corporate pitch within 30 days of starting with me, because I want to make sure that everyone on my team all the way down to like administrative help, knows what problems we solve, who we are, and why we solve them and how we solve them and why we're unique. So let me just take that one step further. I am not a huge fan of cybersecurity marketing. There's like, I don't know, 5000 of us in CrunchBase. There's lots of different companies. And I feel like marketers in general in cybersecurity, say things like we protect all your data when we just do this little thing, like little part of it. And so what I am passionate about is trying to communicate that biosecurity is what we do is very, very important. But it is just a part of the security that you need. And here's the reasons that we are the best. And so we if you look at our tagline, it's it's data aware data, where's the big is the big team, that means that we don't we want to block all of the sites in the data, we make sure that the data that you care about, whether it's it's confidential data, or it's your IP, that that data stays safe. So we do it based on what type of document or file or where are you and who are you? And is that behavior that you usually do every day? Or do we TCC something different? We do it based on what the data is, and that's really different.

Ben Kaplan  9:45  

When you're in an industry where you and your competitors sounds similar, where it's difficult to find the whitespace How do you break free? If everyone says they are customer focused, technologically advanced and incredibly flexible? How do you demonstrate that you are in fact, head and shoulders above the rest.

Diana Massaro  10:07  

That's because it's not because people are trying to lie. It's that when you take that value proposition of any cybersecurity software, and you start making it high enough so that it's comprehensive of the whole portfolio, you end up staying same things. I joke around the cybersecurity marketers have just 10 words, and we just like roll the dice, and we just pick words and put them in different order. What

Ben Kaplan  10:29  

are the 10? What are some of the 10, cloud native,

Diana Massaro  10:31  

seamless, flexible data? Cloud? I mean, it's just all the same thing.

Ben Kaplan  10:39  

The stuff that if it's used enough in sort of a imprecise way, that just kind of jargon, it starts to lose all meaning to anyone, like if you say it's seamless, what are people understanding by the fact that it's seamless? What does that mean?

Diana Massaro  10:51  

factly. Easy, I don't know, I don't use that word. Like when I see that I tell I people laugh at me. But I'm like, No, that's marketing BS right there, you can't use that word. The way out of this is to be use case driven, and to talk about examples of how you solve specific problems instead of of only focusing on the highest level message. So what that means is, it's a harder job for marketing, because we have to get very specific about the target market and what problems we solve. You can only do this as a marketer. If you know the customer, you understand the buying criteria, and using criteria and really what you do, and how your products. So I realized really, in this job, I branded myself in the last couple of months, I'm a product focused CMO. And I think every marketer in cybersecurity needs to be product focused.

Ben Kaplan  11:50  

And what that means, because that's different than like some of your product lead marketing, which is a little bit different. They say like, let's kind of like let the product do the marketing for you built into the design of the product, it kind of helps you market. A lot of sass apps are like that, right sort of naturally kind of promotes itself. You're saying product focused marketing, which actually means let's focus on real use cases, real pain points, real solutions, and be precise in the language we use and very specific as opposed to general and we're, I don't know, I'm trying to think of it some somebody would end up on your top 10 list like 300 360 degree solution. Were turn key for this, where I'm trying to think of what else one could say which you would if I was on your team, you would be taking a red pen to all of that and crossing that out. Correct.

Diana Massaro  12:38  

I when I was at RSA a few weeks ago, and I just was walking around just like oh, that's bad messaging, that's bad messaging. Ooh, that one's good messaging. And, you know, going through all of the different the different vendors, I think, way that this kind of ends up being executed is that you start with, who are you going after, like, who is who's a target that cares about what we haven't as a problem. And we'll be looking for solutions like ours, because we really solve a serious problem than that we have in the industry, you say, where are these people going to be? Where did they look for information? And I've had, I've had countless calls with either prospects or people who aren't even prospects. And I say, where do you where do you go to learn about about security solutions when you have a problem? So number one, no surprise is I go to my peers and my friends, right? We need people to have a good experience with our software and then talk to other people. So you say where are these people going to be? Okay, they're going to go to, I don't know, this, this show, or they're going to read this publication, or they may be doing this thing, or they only care about like small events with their peers. And then we plan our marketing campaigns. You don't say, Hey, we're going to spend X gazillion dollars on trade shows now, which shows we get to, we start with, who cares about this,

Ben Kaplan  14:04  

I would sort of message it when we talk about on our team or for our clients is you first instead of me first, like you, meaning you're the customer we orient ourselves around you as opposed to say, it's me, which is like, Here's my message. Here's what we're trying to say here's what we're trying to do. You're kind of reverse engineering engineering that from from them, correct. Like the way

Diana Massaro  14:27  

you do you said that I also say like, let's start with the problem instead of the solution. Like we never want technology out looking for a buyer. Right? We want we want to be the company that solves real real problems. And that's one of the reasons that I that I came to sky high. This is our when I was when I was interviewing our CEO G Rittenhouse. She's focused on protecting customers. And there's so much money being poured into cybersecurity that I felt like like a lot of companies were just there Because we can get 40% growth, and then we can have great incident and we can all be rich, and he didn't talk to me about that at all. He talked about what the real problems were, are with securing data in the cloud and how we can really help help companies enterprises be safer,

Ben Kaplan  15:17  

as you're trying to to have everyone on your team, you know, get that corporate pitch down within 30 days, how do you do it? Because you have the added challenge of that there's a lot of companies that are in fast growth that might be hiring, but you're kind of starting from like standstill because you didn't exist as an entity before March, now you're growing, I know, you know, the size of your team is growing. So how do you start thinking about cmo as a leader of people, as a leader of a team, you want them to get that kind of the be able to explain to others your reason for being why you do what you do how you do it. But how do you do it, when there might not be a whole kind of culture built up? That kind of reinforces this, right? When you're starting from standstill, you have resources, but then you've got to get moving fast.

Diana Massaro  16:04  

And that's part of why this is my dream job. Like I love this. And worse than that, because we don't have an office, we're all remote. And the CEO is new, and his executive team is new, my leadership team is new, and we're adding a bunch of people. So I jokingly say it's like riding a unicycle while spinning plates. And then someone also is trying to light you on fire. Like it's fun and a little scary and crazy. And it's a it's a very challenging, challenging job. So the situation that I walked in is I had some people on the team when I started, like people who had been dedicated to the cloud business at McAfee. So, for example, Product Marketing, was already in place. But after that, I had to basically create an empty org chart based on my budget, and then have people opt in. So I did have some people who said, I want to work at sky high, who are already part of that McAfee enterprise and got some amazing people. And then we've been recruiting like crazy, and I've got quite a few people right now who have who I've accepted. And who will be starting in the next six weeks, which is a really interesting challenge. Because my team based on the size today, it's gonna grow 44% in the next six weeks, and we're looking at how do we how do we build a culture when I haven't even been able to meet everybody in person? And so I've really been thinking, I've been thinking about this problem, how do you quickly build trust and culture in a remote environment, because that's, that's what I'm in. And what I found is I have to be more authentic and open and vulnerable than ever before.

Ben Kaplan  17:44  

That's an interesting word. Because the idea in a cybersecurity company being vulnerable, it's a word you don't hear a lot, or you hear it like what are the things we solve the talk about what you mean, and specifically, why that helps you with leadership? And why that would, I think two years sort of phrase to kind of build trust faster. Because if

Diana Massaro  18:02  

you don't have a personal relationship with someone and have an assumed the best and have empathy for their position, then it's really hard to have conflict. And that's really what we're about is taking good ideas and figuring out who's the best and how do we work together and marketing's? Well, you obviously know this, but marketing is one of these functions where you have a duplication of function, like everything that happens goes across the whole team. So having rest and and being able to handle conflict is is essential in marketing to be able to function while

Ben Kaplan  18:38  

one of the interesting things about team building is that if you're a growth oriented company, you can't ever just keep the status quo. If you're growing a team members aren't, they will feel like they are falling behind. So how do you align the growth culture of the organization with the growth of key individuals, Diana says you have to make each team members growth a priority above virtually everything else.

Diana Massaro  19:06  

I'm gonna give you my view on this. I don't. So my goal is for my employees to grow and be successful. It's not that I don't care if they stay on my team, but I don't think if they want to go to another role in the company, I will 100% support that. If I don't have the job for them to grow to the next point in their career, and they need to go outside the company. I've helped people do that too. So I've decided that I make a commitment to the human and the person and then I help them with how we grow their career that I find that makes everything so much so much clearer. And the impact of that is that people want to stay with me. I know it's a little counterintuitive, but I really think it works. Well. Let's

Ben Kaplan  19:56  

say like, you know Reid Hoffman who now now Now as an investor, but you know is kind of famous for for LinkedIn and being the CEO of LinkedIn, one things he talks about is this alliance that is formed between the company and a person and without alliances is that the person signs on and says, I agree to sort of put my time and efforts and skills into advancing the company forward. But then the company has to also say, we agree to do what we can to help you move forward in your career for where you're going to go. And that the best companies, especially with critical people, formed this alliance. So is that some of what you're saying to because if you look at their holistically where they're trying to get to, very few people are gonna stay in a job for life, most people are gonna shift. Even during this, I guess, this time of the great resignation, there was a lot of shifting. So you're saying it might just be better strategically, overall, to center yourself around helping the person get where they go. And in fact, that might, in fact, be the thing that causes them to stay.

Diana Massaro  21:10  

The other thing is, people will come back. So I was I was looking for a specific role. And I went to LinkedIn. And I saw someone who used to work for me a long time ago, 18 years ago. And I contacted him, and he's one of the people who's going to start on my team. So people will come back to the same company, I tell people, when they leave, if somebody says, Hey, I'm gonna go somewhere else, I'm like, I'm so proud of you, congratulations. If it's not what you want, or your career progresses, and you want to come back, just let me know, in the in the sometimes do and you get these wonderful people who then have gone out and had different experiences and come back and they're even stronger. And so I find that it's I don't know, it's like, it's like business karma, you know, they come, it comes back. And I didn't always feel this way. And by the way, your quotes on Reed Hoffman, like, obviously, he's thought much more about this than I that I have. I'm still just just doing what I think is right without sort of sort of thinking all the way through. But I do, I do know that I can't be successful without great people. And the way to recruit and retain great people is to treat them holistically with respect, and trust them, and listen to them and understand that there are people first and part of their part of their their experiences work.

Ben Kaplan  22:37  

You've been split off from another company, there is some legacy there you're bringing people in. And you've got to make out this org chart, you mentioned that you're increasing by 44% in the next six weeks, just in terms of headcount. So how do you think about that org chart and the context of people fitting into that meeting, you need a certain number of really strong individual contributors who are just like have great skills, need a certain number of people who are managers that can manage and kind of direct us and align us and get us in the vision can be all individual independent contributors, you need others who are people who are kind of the glue between things that just allow connectors as a good way to Google glue people, that's a better term that you said connectors as well, if you do all that, and you have to build this and you have to build this quickly. So how do you think about that org chart for someone that has to do it kind of build one from scratch, or really change one in a short amount of time? I love that

Diana Massaro  23:35  

question. So I was super fortunate. So when I when I came in, I said Okay, the first thing I have to do is I have to build my leadership team. So I had, you know, boxes of six boxes. And a few of them were already filled with amazing people who had already been at McAfee some of them only year. Some of them I have two leaders who had been at McAfee 18 and 19 years

Ben Kaplan  23:59  

and when you say six boxes, why six? Is there like divisions? Is it how's it organizes their kennels? Is there

Diana Massaro  24:06  

actually the marketing function so I did you know, corporate communications and analyst relations is very important to us. That's a box and demand gen.

Ben Kaplan  24:16  

Okay, so these are like traditional channels that you're going to market in there's going to be leaders for each of those gotten.

Diana Massaro  24:20  

So I'm just lucky that there were some natural leaders that either opted in or were already there. And then where I still had open boxes, I pulled from my network and I had I got those within within probably six weeks of starting this job I had all of my leadership positions filled

Ben Kaplan  24:42  

because you've got that you've got the the heads of each of the channels then

Diana Massaro  24:47  

they had to go staff their teams and that's where we're seeing all of the team the other people coming in so I've been you know, we're helping recruit that so I mean, in the kind of tell him like, hey, my team staff What about yours? So then they have to go and find, find those people, but I hold my leadership and my direct reports responsible for their functions. And so they need to go find the best people they can, some of those are going to come internally, and some of those are going to come from my network or their networks. Most has been done through referrals, most of the people that we're hiring are through referrals, or some one of us has worked with them before.

Ben Kaplan  25:24  

And when you're building a team like this, are you just evaluating each person on the merits of the person? Here's our role, you know, did they fit that role? Or are you thinking about how these people kind of fit together? Meaning like, oh, I, you know, this person who has this very, I don't know, quantitative background, this would be great. paired up with this other person who brings something different, or at this point, he's got to hire you got six weeks, you just got to get people can fill the role? How do you think about the team dynamics versus the individual person?

Diana Massaro  25:58  

Well, so because we're going because a lot of it is referral, it's easier for us to, to know that they're good, and they're gonna fit because we've got, you know, we have experience with with them, to some extent, we are still, so let's just give like, like a role like a someone to manage manage our customer program. So our customer marketing manager, you know, that's a pretty like, again, in marketing, it's like, it's a pretty defined role of what that person is going to going to do and how they're going to grow that. So one of the things that we're looking at is for our individual contributors to be able to move up. So we are a little bit sort of over hiring or trying to get people that we know can grow with the organization, because I expect that we will, we will grow and increase the marketing staffing over time. And I want to always be able to hire in at the bottom and then provide career advancement for the people that we have. So that's one of the things we're looking for. I have I have this thing called the lunch test. So when you interview someone, if you don't want to go to lunch with them, you shouldn't hire them. So there's a little bit of likeability, it doesn't mean that they're socially well adjusted, because I like crazy people, obviously, like a little bit of a little bit of mental illness is good.

Ben Kaplan  27:19  

Okay, okay. Sure.

Diana Massaro  27:21  

I do, I do have a bunch of tests. And I've had in the past, I've had managers come and say, You have great skills. Here's what they said. And I said, Well, did they pass the lunch test? Did you get lunch alone with them? And I like no, like, you can't hide

Ben Kaplan  27:36  

it? Well, interestingly, this is a different lunch test. But Thomas Edison, obviously famous inventor was famous for his lunch test, because what he would actually do with people to hire when he was hiring scientists, he would actually, you know, they'd order lunch, and he would see, he would observe how they ate their lunch. And actually, if anyone salted their food, or added some kind of spice to it, without trying at first, he wouldn't want to hire them the reason because they're in his line of work, they're making assumptions about the food. And they're not actually testing and trying, and he wanted people who didn't make assumptions. So that there you go different different lunch tests. But now you can look and see, are they putting the pepper on that, and then the and then you can make a hiring decision,

Diana Massaro  28:20  

I have my own tests like that. If you don't have excellent writing ability and good grammar, then you won't get hired. So if I see no

Ben Kaplan  28:31  

matter what the position, even even if it's a marketing position that has nothing to do with writing, doesn't

Diana Massaro  28:35  

matter, everyone in marketing history. And so sometimes I do encourage some email communication back and forth with people. So we can see one, one intern candidate once responded from her phone. And it wasn't, it was she didn't she didn't prove it well enough. She didn't get the job. And the next year, she came back in and she said, I'm going to try this again. And she's she was wonderful. We actually ended up hiring her. But yeah, you got to mean I have I have one test like that. So if you're applying for a job at Skyline marketing, careful what you write,

Ben Kaplan  29:09  

okay. If writing ability is a critical skill for a marketer, what other skills round out the ideal cmo skill sets? At top agency we have a unique litmus test. Our reason for being is to combine the left brain analytical skills of performance marketer with the right brain creative skills of brand marketer, and we hire across the organization looking for that rare combination. If you're on the CMO track, I want to ask Diana, what other skills do you need?

Diana Massaro  29:42  

So the first the first thing is to understand what is the difference between a VP of Marketing and a CMO? Let me tell you my personal view of that. So VP of Marketing knows all the marketing functions like how do you run trade shows and measure that and how do you get messaging out and how do you do Always, a CMO looks at the company strategically and understands where the industry is going, where the competitors are going and has that higher level of being able to really talk to industry analysts and be part of having a strong voice in the direction of the company, whether that's should we do m&a? Or should we look at this type of value proposition? What if we went into this market, so that real voice on the on the executive team, that's to me, what differentiates a CMO versus a VP of marketing. So if you're, I would say the best thing is to get as many as much experience in various disciplines as you can. One of the things that makes me an incredibly strong marketer is I have been in product management, professional services, I was CEO for a couple of years. So I understand how the company works, I understand financials, I understand, I understand the inner workings of a company and the relative importance or not importance of working. And then so the first thing is get as much experience as you can in various functions. And the second thing is really is start reading, start trying to understand a little bit more about the industry. And the customers get as much customer and prospect feedback as you can.

Ben Kaplan  31:23  

If the difference between a VP of Marketing and a CMO is that sort of perspective on the whole business that goes beyond just the specific functions of marketing, then what is the difference between a great cmo and an average cmo results?

Diana Massaro  31:42  

I'm laughing but it's true like like if you mean a great cmo helps drive success in the business. Like that's it, the sales, the sales leader and I have the exact same goal. We succeed and fail together. So a great cmo helps the business succeed. I mean, that's it, it's repeated.

Ben Kaplan  32:06  

According to Diana Massaro, CMO of sky high security, don't be timid. Be fearless. When you're new to a business, find out as much as you can about how the business operates, not just about specific marketing functions. Read the reports, do your research, understand the industry you're in and where it is headed. Be absolutely selective in your hiring become a champion of Team growth, and the individual careers of each team member. Remember, we're all human first. So choose people for your team that you'd want to go into battle with. And before you go into the foxhole, you've got to want to go to lunch first. Align your marketing objectives with your revenue objectives. And you'll always have a seat at the table. Good CMOS, Craig, good marketing, great CMOS accomplish great business objectives. For top CMO, I'm Ben Kaplan.

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