Supporting economic advancement among women in cybersecurity | Cyber Work Podcast

Christina Van Houten talks about [email protected] and women in cybersecurity on this week's episode. We discuss tactics for bringing more women and diverse candidates into cybersecurity, the importance of a well-balanced and skills-diverse team, and how the work of Chief Strategy Officer is like an ever-evolving game of Tetris!

0:00 - Intro
2:30 - Van Houten's origin story
4:13 - Strategies cybersecurity was lacking
7:05 - Accomplishments that helped bolster her career
13:46 - Average day as chief strategy officer
18:03 - Entering cybersecurity in different ways
20:37 - [email protected] and trying to help
26:27 - Bringing more women into cybersecurity
29:20 - Making careers accessible to women
34:14 - Diversifying upper management
36:22 - Success stories mentoring women
41:01 - [email protected] book and men in cybersecurity
46:33 - Roadblocks women in cybersecurity face
50:47 - Projects from Mimecast
54:37 - Outro

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    • [00:00:00] Chris Sienko: Today on Cyber Work, my guest is Christina Van Houten of Mimecast and the creator of the [email protected] website. We’ll discuss tactics for bringing more women and diverse candidates into cyber security, the importance of a well-balanced and skills diverse team, and how the work of chief strategy officer is like an ever-evolving game of Tetris. That’s all today on Cyber Work.

      Also let’s talk about Cyber Work Applied, a new series from Cyber Work. Tune in as expert infosec instructors and industry practitioners teach you a new cyber security skill and then show you how that skill applies to real-world scenarios. You’ll learn how to carry out a variety of cyber attacks, practice using common cyber security tools, engage with walkthroughs that explain how major breaches occurred and more. And believe it or not, it’s all free. Just go to infosecinstitute.com/learn or click the link in the description below and get started with hands-on training in a fun environment while keeping the cyber security skills you have relevant. That’s infosecinstitute.com/learn, infosecinstitute.com/learn.

      And now let’s begin the show.

      [00:01:12] CS: Welcome to this week’s episode of the Cyber Work with Infosec podcast. Each week we talk with a different industry thought leader about cyber security trends, the way those trends affect the work of infosec professionals, and offer tips for breaking in or moving up the ladder in the cyber security industry. Christina Van Houten is a veteran of the enterprise technology industry having spent two decades with some of the world’s largest firms including Oracle, IBM, and Infor Global Solutions as well as Netezza and ProfitLogic, the entrepreneurial companies that were acquired by them.

      Currently, Christina is Chief Strategy Officer for Mimecast, a global leader in cyber security where she leads product management, product strategy, corporate development and M&A. She also serves on the board of directors for TechTarget and has been involved as an advisory board member of several emerging technology firms. In 2017 Christina launched [email protected], a resource platform dedicated to the economic advancement and self-reliance of women and girls around the world. All these accomplishments and more are going to be the topics of today’s episode. We’re going to talk about women in cyber security, the [email protected] program, and more strategies to bring a more diverse workforce to our industry.

      Christine, thank you for joining me today on CyberWork. Christina. I’m sorry.

      [00:02:25] Christina Van Houten: Thanks for inviting me. I’m really excited for our conversation.

      [00:02:28] CS: Thank you very much, Christina. I appreciate that. I always like to start out, and you’ve had a quite storied career, but how did you first get interested in cyber security and computers and tech? Your bio straddles a lot of different fields of interest and skill sets. What was it about cyber security that you find interesting or compelling?

      [00:02:45] CVH: Yeah. I’m sort of a latecomer to cyber. I’ve been in tech for over two decades, and I just have certainly always had to think about security as owning ERP products, enterprise, technology products, infrastructure, but I hadn’t had a deep domain experience in cyber until Mimecast reached out. And I think what was really interesting about our CEO, Peter Bauer, is he realized that there was a broader perspective from having been in all different parts of enterprise technology that could add a lot of value to cyber. And that what the space was about to undergo as it had been emerging and lots of different categories proliferating and the need for more of a sweet approach and a more holistic way of thinking about the problem and helping organizations solve it in a way that was more consumable, that there was some fresh perspectives from outside cyber to bring to that and saw that opportunity with me uh combined with a lot of deep domain cyber that was already in the business. That’s how I’ve ended up there. And so three years in, it really has turned out to be that way. That evolution is kind of fully underway and I really enjoyed being able to dig in and become an expert I guess in the industry while also maintaining this broader perspective as well.

      [00:04:14] CS: Can we drill in a little bit more about sort of what strategies that cyber security in this area was lacking that you were able to bring in from like an entrepreneurial or these other sort of business standpoints? What was the synergy? What was the collaboration that was missing before?

      [00:04:32] CVH: Yeah. I think cyber is a really challenging dynamic space. And so you have these kind of slivers of best of breed capabilities that had been emerging. And for the most part that had attracted people who had very acute expertise in a very discreet part of solving the problem. And so I think that really serves an area of a business well in the early phases of a piece of technology emerging to solve a problem. But I think over time there’s a lot of Darwinism in tech as there is and everything in life, but especially in tech. And so I think being able to see connections and see how the problem is morphing and see where you can kind of look outside of your particular sphere. And I’ve seen that in many cases where coming in sometimes I would come in and think, “Well, how am I going to add value to this?” But by just asking a few questions I would in many cases see connections that maybe other people didn’t. And even the most um advanced engineer who’d been working on something for a long time would say, “Oh yeah, we could use this thing to solve this thing as well and end up with a better, a faster solution, something that’s more efficacious and also easier to use and more cost effective.” There’s been kind of a series of that adjacent innovation pieces of conversation as we’ve been able to bring different capabilities that we developed organically and taking like a nugget of something and apply it to doing something else, but also bringing entirely new capabilities through M&A and just the catalytic effect that those have injected into the business and also into our technology where you really get what we call a sweet multiplier effect by combining things in a way that each becomes better on their own and you’re sort of sharing complimentary things. That’s been a lot of fun. It’s like – I don’t know, Sudoku, or pick your favorite crossword.

      [00:06:58] CS: You want, like Tetris, you feel the pieces are falling perfectly into place. It’s very satisfying

      [00:07:04] CVH: That’s exactly right. Yeah.

      [00:07:05] CS: I love it. I want to talk a little more about your career. Can you tell me about some of the major stepping stones in your career? Because you’ve got some pretty impressive company names in your background, Oracle, IBM. What were some of the accomplishments or successful projects or just aha moments that helped you move up to your next levels of your career?

      [00:07:24] CVH: Yeah. It couldn’t have been more random or weird for meandering. I was a liberal arts under – I’m 54. I graduated college in 1989. Tech was hardly a thing then. I learned how to type on a manual typewriter in catholic school from the nuns. I didn’t even take a computer to college. I think I owned my first computer in graduate school. I wanted to do public interest work. I wanted to do community and economic development and low-income housing and all kinds of – And I did a bunch of things around all of that in my 20s. And I ended up very randomly evolving into a job in tech in the late 90s and frankly never thought I would be good at it. I think I was intimidated by it. I had not been a STEM girl as somebody might say now. And so I sort of fell into it and then very quickly realized that I just was something that was very consumable and that’s something that I was very good at, that I was very energized by the problem. Again, back to our Tetris thing, the problem solving pieces of it, the opportunity to work with this incredible continuum of personalities and nowhere do you get the diversity of personalities that you do in enterprise technology companies because you get these brilliant usually extroverted sales guys and gals who are out there and amazing storytellers and thinkers and engagers. And then on the other end of the spectrum you have these brilliant engineers who are just amazing, quiet leaders, earnest guys or/and gals who are just – I just have so much joy in getting to collaborate with them and envision solving something for an end user or a whole category of problems or verticals.

      And so I very quickly um just dug in and realized that this was the place for me. And the first inflection point, back to your original question, was I was still feeling my way, but I pretty quickly ended up leading the sale, a four million dollar sale in this emerging pretty small company. It was the first big license deal they ever did with a giant tier 1 retailer. And I thought – And it had been a really difficult sale. It had been lots of engagement and conversations and design and all that. And then the opportunity to then really dig in and build something pretty advanced. And so that was sort of the first major inflection point.

      The second was I ended up having two babies like 18 months apart. This was my mid to late 30s. And it was at a time where I couldn’t have been happier in my career and more worried about what is this going to do to that? How are these babies going to mess all this up? Coming back and realizing the opportunity to pivot, like the role that I was in wasn’t the only role that I could add value in, and evolve from more of that role of product management sitting in between the customer in the field and the engineering work to actually being much more embedded inside of engineering. And that was such a great – At the time I thought, “Is this going to hurt my career?” Because it was kind of a lateral move or maybe even a step back. But in the end I think it was one of the most important things I did because it gave me much more an on the ground technical engineering role.

      I ran common components and build engineering along with just kind of overall engineering operations and release and launch management and those kinds of things. And so all of that, and developing a whole detailed product development life cycle, and those were things that have still stuck with me and it enabled me to accommodate my personal life and keep going in my professional life. And I think for women out there realizing that you can make those pivots. And if you can show up and think about what the win-win is. If you’re gaining those bits of experience, it’s very expensive for employers to lose you and they’re probably more willing to accommodate you than you think if you can brainstorm that.

      And then the last – Everything has to be in threes. The third I think big moment was not too long after that I’ve been at this company for five years when Oracle acquired it, and I’d never been acquired like that and I’d never been part of a company that large. And I went in assuming that especially because I had two young babies still and one of them was particularly challenging at the time. And I thought, “This isn’t going to be for me.” But sticking it out and, again, kind of figuring, looking, kind of keeping my head down during all the chaos that ensues after an acquisition, but also keeping my head up and seeing where I could add value on my own without anyone asking. Creating something, seeing who was in charge and who I could who I could help in a world where there were lots of unknowns. I dug in and created something, a business value for who was then the general manager. And from that point he sort of took me, plucked me out of where I was and took me along not only through five years. I ended up five years at Oracle, but then uh also my seven year tenure and four as well.

      There are these moments where I think if you can –Especially in sort of that emerging part of your career, be willing to move sideways, be willing to take initiative around creating something for someone in the business that no one asks you to do that you might be uniquely positioned to do because it’s frankly tedious and hard, and/or hard. That can lead to moments of inflection that open new doors and opportunities.

      [00:13:46] CS: Let’s talk about your current job. What is your average workday or work week look like as Chief Strategy Officer at Mimecast? What are some tasks or projects that you do every week?

      [00:13:56] CVH: Yeah. I think the reason I’ve kind of stayed in this area of the business from pretty much all of the 22 years is that that area between the people who carry a bag and the people who code is because of the opportunity to do such a hugely diverse set of things. And I think some people really prefer predictability. They want to know what their role is. They want to know what’s expected of them. That’s not me. I like a little bit of – Or a lot of ambiguity, a lot of sort of hairy things that need to be solved and disorganization that needs to kind of brought together in one way or another. And I love being able to see an end game that maybe everybody else doesn’t see and then figure out how to map back to the starting point. Get those people together and then sort of together move our way toward that promised land or that amazing thing that you’re creating.

      [00:14:58] CS: Like you said. It’s a lot of that problem solving and the minutia and sort of finding surprising connection points and stuff. Is that right?

      [00:15:06] CVH: Right. And I would say constraints breed brilliance. Like you’re always going to run into things you didn’t expect. You don’t have enough money. You don’t have enough time. Looking at that is a challenge. I mean, an opportunity really, more than a challenge. And something that hey – And you can really uncover something that maybe you didn’t think of. Again, back to my role, I think one day we might be building wireframes and a prototype for something new. The next day we might be engaging deeply with customers and getting their feedback from all over the world. The next day we might be really engaging with engineering on like our best practice around our whole product development life cycle. And are we doing the right thing around the way we’re writing requirements and handoffs and getting product out the door? How do we want to measure success? Are we tracking the right KPIs and how do we want to evolve that? That diversity, even extending into support and feeling a huge level of empathy and engagement around not just getting something out the door, but what happens on the day-to-day basis? How does it feel to be using the product and how can we make that better? Whether it’s in the core technology or surrounding pieces of it?

      One we’ve really focused on in my team is something – I started climbing the softer side of security. And as a Chicagoan who probably maybe loves Sears somewhere in your heart, even though it’s gone, but not forgotten.

      [00:16:45] CS: Oh, we don’t call it that other thing, right? It’s still the Sears Tower.

      [00:16:50] CVH: I’ve been calling it the software side of security. What we found in dealing and engaging with our customers is it is crazy. I was kind of a backroom guy. I’m a techie guy. I’m not a marketer, and yet I’m finding the most challenging part of my job is engaging with my stakeholders and managing change with end users and because they’re paranoid that your big brother or just the complexity of how things is just –

      [00:17:16] CS: Just going to make it too hard for them or – Yeah. Yeah.

      [00:17:19] CVH: Yeah, exactly. You’re going to get in the way of productivity, and then also explaining to executive members or boards on Monday mornings, like you’re spending and spending and spending. What is enough? How do you measure risk? And like helping them put some concreteness around how good am I? Am I getting better or worse? How do I compare to my peers? If I’m a mid-market healthcare organization in the US, am I better or worse than all the other mid-market healthcare organizations in the US? And so that’s something, that softer cyber security that we’ve been focused on as well as just kind of the core, “Hey, stop bad stuff from coming in,” and then fix it fast if something does get through.

      [00:18:02] CS: Right. From a work standpoint as well, we drill this home almost every week, but for so many people who think that the only way to get into cyber security is by coding or by pen testing or by doing this or that, like there are so many vital important jobs that involve other aspects of cyber security. Whether, like you say, it’s making sure that it’s integrated properly or that people are comfortable with it or that stakeholders understand the scope of it. And those are real jobs with real important skills and real outcomes that affect things as much as tuning the firewall up correctly or blue teaming or anything like that. If you’re worried about it, then – “Oh, I’ve been a lawyer my whole life.” “I’ve been a veterinarian my whole life.” Like there are still these paths in as you’re basically saying here.

      [00:18:52] CVH: Yeah. I’m so glad you mentioned that, because like I said, I’m kind of new to cyber security and I’d like to think that I’ve brought a lot of value to the company that wouldn’t have otherwise happened. And since I’ve been here, I’ve also brought in several people especially women who didn’t necessarily have any legacy in cyber, but are some of the most impactful well-known people in the company. And one of the most rewarding things for me not just at Mimecast, but my whole tech career, is kind of figuring out that magical cocktail of personality traits. You probably know about portfolio optimization and investments. And I think there’s an analog to teams where you can have sort of high-beta people who are kind of really creative and energetic and add a lot, but they’re also sort of maybe a little bit unpredictable. And then you have some people who bring kind of this really steady execution focus and an ability to always kind of see things through. That magical combination of talents and personalities that together really enable you to envision and achieve something that would otherwise never be possible with a homogeneous group or a single individual is really the fun. And seeing that happen and seeing what that ends up meaning for those individuals in their careers, like finding a round peg round hole. And then also watching teams just uh feel good about achieving something together that otherwise wouldn’t have happened has really just been an amazing thing for me.

      [00:20:38] CS: That’s fantastic. Along with, or in conjunction with your work with Mimecast, I learned that you have made it your life’s work to help uplift and support the economic advancement of women in the workplace and cyber security and in all aspects of work around the world through your mentoring and educational organization, [email protected], as well as your books [email protected] and [email protected] and much more. I wanted to start by talking about your long-standing mission. How did you start helping in this way? I’m sure a lot of our listeners would like to know how to get involved with solving problems that are important to them but might not know where to start. Let’s start with that question. The moment you realized that you needed to help women and girls get ahead in the world, what was the first thing you did to begin helping and where did it grow from there?

      [00:21:19] CVH: Yeah. I went to Georgetown in Washington, D.C. and I was there in the late 80s and there was a lot of community and economic struggle during that time period. And so I started working in transitional housing facilities. Anybody who’s maybe too young won’t remember this, but kind of the crack epidemic was in full swing and there was just a lot of poverty. And so I started getting engaged then, and that that inspired kind of the first ten, almost five to ten years of my career, where I was really committed to being involved in social change and, again, when I started talking about community and economic development and public policy and those kinds of things.

      That was a real focus and dedication early on my career and I thought it would be a long – That’s what I would be doing forever. But as I got out of business school and I randomly ended up in tech, I felt like I’d gotten away from that. And I had micro-level opportunities to continue doing it during my career in the private sector. And one of the things I realized through that is how – I think early on I thought, “Oh, I’m kind of selling out by going away from what I was originally doing,” but realizing that the private sector is really an opportunity to be incredibly magnanimous, and there’s really no better way to serve sort of that original mission I have than to give someone a job and give them an opportunity to realize a career that they would never have otherwise had and that they completely earned on their own but they may not have ever had that opportunity to get their foot in the door. And I’ve been able to do that so many times over for the last 20 something years. And that has been so fun and fulfilling. And then in my late 40s I suddenly started getting asked to speak to more and more groups of women. At first I was like, “Why does anybody want to hear from me?” Especially because I would get in front of these groups of women who were amazing, and they had been engineers like right out of the chute. And I frankly still felt like a complete imposter. I think everybody sort of has some level imposter syndrome, but I still was.

      But even though kind of I felt just a little uncomfortable with it, and every time that I had the opportunity to do it and all of a sudden it was happening quite a bit, I walked away just realizing I would get all these notes and just overwhelmed with gratitude. And I started to think, “Well, maybe there there’s an opportunity here and an obligation.” And the opportunity to get back to kind of what I originally wanted to do but in a way that made perfect sense for me given how my career had evolved and where I was at this point in my life. And so the other challenge around it was that I had really pretty much this whole time been traveling. I always had jobs where I was on the road. I wasn’t someone who could say, “Oh, I can show up and volunteer or do this thing on this day.”

      And so having this epiphany that there were these groups of women who were so hungry for this kind of engagement and advice and guidance at a time where I realized that I could achieve kind of a publish and – Like a very high-scale publish and subscribe model around not having to be there, but to have content and to have a platform that connected women to each other that you didn’t have to rely on your network just in your immediate – And your immediate sphere. Especially for women –

      [00:25:11] CS: Right. Especially if you don’t have one. Yeah.

      [00:25:12] CVH: Yeah, exactly. Like so many women, their parents, they’re the first generation in their family to have the opportunity to go to college or be this kind of a technology field, and so to be able to reach around across the world. So like when I set up that mentor matching program, one of the most rewarding things was to start to see Women in India ask for appointments with women in the US or vice versa, or women in US asking for appointments with someone I had from South Africa or the other way around. And so um that’s really –It’s been really interesting.

      The thing that – There’s so much more I want to do with it. So I have this whole curriculum that I’ve written around – I call it the One Day MBA, but I haven’t launched it. I have a third book called [email protected], a career guide to navigating pregnancy and parenting. But it’s served its purpose so far and it’s just brought me a lot of joy and I hope that it’s also opened opportunities and connections and guidance for women who wouldn’t otherwise have had it.

      [00:26:27] CS: Yeah, it sounds like it has. Every good act is an act that moves everything forward. That’s very gratifying to hear just how much you’ve filled this need and sort of inspired people. I want to move, sort of focus down into cyber security. I’d love to talk to you about the work of bringing more women into the cyber security field. I guess first to ask, what has been your experience as a woman working in the cyber security field and what are some common policies, prejudices or underlying and unaddressed issues in the cyber security field that you’ve seen holding other women back or caused unnecessary roadblocks for them?

      [00:27:06] CVH: Yeah. I’ll talk about the field more broadly, but I’ll start with just my experience at Mimecast, because when I first came in the team that I ended up bringing together, there were a few different teams that were brought together and there were almost no women on it. And it wasn’t anybody’s explicit decision to do that. It was just kind of the way things naturally evolved. And I mentioned that just because it was such an example of what you’re saying around these individual things that happen that have a domino effect or catalytic effect. As soon as I was in that role, suddenly women from inside the company who are maybe in sales who didn’t want to be in sales anymore who wanted to stay in the company approached me and said, “Hey, I want to come work with you.” But they wouldn’t have had –There had not been a female leader in that role. They wouldn’t have done that. And they’ve turned out to be just absolute rock stars. I can’t even imagine our business without them having evolved into those roles and also what it meant for them in their careers. And then also at the same time that the outside talent that I I’ve been able to attract based on that.

      And I’ll say, and the guys that I’m talking about would admit this. Like in the early days of me bringing in some of that, it was people who weren’t that kind of dyed in the wool deep domain been product managers in cyber for 10, 15 years. They were like, “Why are you using this valuable head count that should be for another one of those guys for this this other role?” But then within a quarter, they were all like, “Oh my God!” They just couldn’t believe what it did for them and our team and our ability to do the things that we needed to do in an extraordinary way because of, again, that cocktail or that optimized portfolio of talents.

      [00:29:11] CS: Yeah, balancing of sort of forces or energies or dispositions or skill sets.

      [00:29:17] CVH: Exactly, yeah. Yeah.

      [00:29:18] CS: Okay. I guess to that end, I want to ask what we can do in the cyber security field to not only make cyber security careers more accessible or desirable to women, but also sort of go beyond moving roadblocks out of the way and move toward actively seeking, recruiting, encouraging a more diverse set of professionals to enter and enhance the industry in this way.

      [00:29:41] CVH: Yeah. It’s such a good question because it’s hard – Most of the actions that have happened since I’ve been there, the before and after picture is so different. And so it’s neat to see that catalytic effect. To think about it being more programmatic and more widespread is an interesting question because I think part of it is – Back to the original point, I think it is a chicken and egg thing because it feeds on itself. If women can see themselves or they see someone who they can see themselves in or who they’d like to see themselves, they’re more apt to sort of all of a sudden imagine and pursue something they wouldn’t otherwise do if they just are looking at a group of people that don’t reflect them at all.

      And so just an interesting example is I plucked a young woman who I knew who was a kinesiology major right out of undergrad, which is physical therapy, and she was kind of – I had known her for a long time. Her parents were first-generation immigrants in the US, and I just had kind of followed her because she was very bright and I kept saying to her, “Does she have a job? Did she have a job?” And I made her come in and interview. And even though I think she was probably like, “Ugh! I have no interest in this.” She’s ended up being – She’s not two years in and just a rock star and absolutely loves it. And so I think when I think about the programmatic aspect, if there’s a way to grab people like that early on into jobs that don’t require – There’s always jobs in the early phases of these – There’s pockets of things where you just need smart people, like hungry male or female. I mean, I’ve hired several people right out of college in the last couple of years. Almost every one of them, I think 100% of them have been unbelievable.

      And what they have become in the organization and how they’ve evolved in six months, a year, is just – I don’t know if it’s this generation or like their ability to learn and pick things up, and it’s literally like they’ve been there for 10 years. I think, again, it’s not necessarily gender specific, but I think if you can make a concerted effort to bring interns in an undergrad and then just proactively – Because the graduation rates are over 50% women and undergraduates and not just look for engineering backgrounds and those kinds of things. I think if you can get that early on and they’re just kind of part of the ecosystem they’re learning and it becomes like a graduate degree for them in the early, and they add a lot of value to the company because they’re able to be good arms and legs and pick things up. And they may not stay in that particular role, but just making it known that those kinds of lateral moves that I mentioned earlier that I made are open to them. I think that’s the other thing that the company can do, companies can do, is make those career paths not so prescriptive especially for those people that are coming in their 20s. They just need to get started. And so they may find that they started in support, but they actually really have an amazing interest and strength and a lot of the work that is involved in product development or QA or whatever it is, or marketing and vice versa.

      I think if it’s possible to almost have those kinds of programs and maybe even let people rotate around the company for a quarter of the time, and then at the end of it it’s almost like you had sort of a fellowship. And we had this at my last company where it was – It was a very programmatic way of plucking people out of undergrad and even business school. They moved around at different parts of the organization and at the end they were kind of fellows and it was something you could put on your resume. And many of them stayed or still at the company 10 years later and some went on to do something else, went back to school or took a job at a different organization.

      [00:34:15] CS: Well, to that end, I want to talk a little bit about the notion of sort of building the bench, to use a baseball term, for female cyber security professionals in the industry, because as you’re saying there’s a lot of incentive to bring women and diverse candidates in at intern levels or at entry levels or getting moves into sort of lower level jobs. But do you have any thoughts on sort of diversifying the upper levels of management, c-suites, etc? It seems like an even taller order in some ways. Do you have any strategies for female cyber professionals that want to sort of promote into upper levels of organizations?

      [00:34:52] CVH: Yeah. I think back to kind of how I ended up here. If you look at tech, cyber’s probably one of the least gender diverse areas just because it is so techy. I think when you get into infrastructure tech it becomes – The numbers get more tough. But I think tech more broadly, if you’re looking across b2c and all parts of b2b enterprise, there are a lot of amazing women who have risen in the ranks. The last company that I was in was a three billion dollar, very broad ERP portfolio, and there were all kinds of women running sales engineering, support, for a massive organization of 15,000 employees and a hundred thousand customers around the world. There’s no reason that those kinds of – That kind of talent. And there was amazing next level down as well like that kind of VP senior director, director level. There were almost more women that had risen in the ranks there.

      And I’m guessing the same has been true like in Oracle. And I spent a little bit of time in IBM. IBM had lots and lots of women. And so I think where there’s an opportunity to look more broadly in tech to women that have risen to a certain point and then give them the opportunity in cyber even though their domain might not be as deep, but they’re bringing lots of other amazing things from a broader experience, and tech might be a way to do that.

      [00:36:22] CS: Yeah. Now, I want to go back to – You talked a little bit about the mentoring program through [email protected] You have a very robust mentor to mentee matching system. And as you said, it’s global and it’s a key component of the site. Can you tell me about some success stories that you’ve seen involving mentors helping professional women clear institutional or cultural roadblocks and succeed?

      [00:36:43] CVH: Yeah. It’s actually been a real range. One of the things that to say about it, we leveraged – Just for those of you who don’t know it, we leveraged – I think of it as like a marketplace. There’s supply and there’s demand. And the way a lot of this was selfish on my part because I wanted to be able to mentor and help women, but I wasn’t able to give a long-term commitment to anyone. And I think that’s true for most women. I didn’t want to have to sign up for like some big mentor training or say, “Hey, I’m going to meet you every Sunday,” or whatever it was, but I felt like there was a lot of value in being able to connect with someone and solve a discrete point in time challenge.

      And so that’s what’s what it’s designed to do. We use like a shopping cart framework through – We’re a platform on Squarespace. So you go and you see there’s an architect or there’s a physician or several different physicians. There are several people in different roles in tech. There’re all kinds of people, designers, and teachers, and coaches, all that stuff. When you pick when you pick someone, and I’ve had some women come on and pick three people they want to meet with. I’ve had some pick one. I’ve had some pick five. In the examples of things are, “Hey, I have an interview next week in this field. Can you just help me dry run it? Or what are the key things that I should highlight out of my background or avoid?” It’s like a real tactical pragmatic opportunity to get guidance from someone who’s very objective. Same with, “Hey, I’ve been out of the workplace for five years. Here’s what I was before. I think this is what I want to get back into but I have no idea how to sort of wedge my way back in. What’s the best way to do that? What are my options?” “I’m trying to negotiate a raise. Like I’ve been in this place for three years. I’ve done this.” How would you go about positioning that? What’s realistic? What’s going to resonate with someone?

      Those are some of the examples I think. Also, just people feelings. I had one example of a woman, amazing woman who has had – She’s now in her early 60s. She’s the most amazing person I’ve ever known. Has been a tech exec forever, lived all over the world and was a woman in sales in tech with Microsoft, and mainly with Microsoft, or when there were just no women, because she’s in her early 60s. And a young woman who I’ve gotten to know in South Africa who’s one of the top sales people now, and she’s probably in her 30s. She reached out and wanted to meet with this woman in the US, and I think part of it was about, “I’ve been selling for a long time, but I just don’t know if I want to sell for another 20 years, but I want to stay in tech and I want my career to grow. What are my options as someone who – Watching someone who is now in their 60s and 20 or more years down the line who’s done a couple of different things and twists and turns and her thoughts on that. I don’t know if that answered your question, but there’s been a lot of very nice of stories.

      [00:40:13] CS: Yeah. Yeah. Yeah. Yeah. Yeah. No. And I think a lot of those times too, like you said, that feeling of stuckness or confusion about what to do next can be answered with two or three authoritative answers from someone that you trust, and sometimes that’s all it takes to get unstuck, is hearing the right person say, “You can do this.” Or, “This is the thing you can do or you just need to pivot in this one small way.” Yeah, I can totally see the benefit.

      [00:40:37] CVH: It is. It’s so true. It is amazing. The thing that always amazes me is people who actually don’t know the problem that well or at all. And that, like you’re saying, just a couple words or just one question phrased in a particularly incisive way that just unlocks something that you’re, “How did I not think of that before?” Yeah, I hope it continues to add value. We’ll see.

      [00:41:02] CS: Can we talk a little bit about your book, [email protected]? And to use the book’s phrase, the process of navigating male archetypes. I would like to know how understanding some of the hard coding of male cultural assumptions within cybersecurity can – If we can use that information to change the culture and make it more fertile for a diverse workforce.

      [00:41:21] CVH: Yeah. Well, first, I just wanted to get a little background on how it started. I was mentioning earlier in my late 40s where I was all suddenly getting asked to speak more and more to groups of women. And I have a colleague from Oracle who’s still my closest friend and he’s 10 years my junior, but he’s so wise and he’s ended up serving as this amazing kind of career and life coach for me on the side. He’s one of those people that shows up with that incisive question that just gets right at it, and he doesn’t he doesn’t let me get away with anything. I can always call him and know that he’s going to give it to me straight.

      Around the time that I was telling him about how much joy I was getting out of this unexpected engagement, he said, “I really think that you’ve become too one-dimensional and you need to do something – You need to pursue something else in your life make your life bigger beyond work, and I’ve always thought that you should write a book.” And you should write a book.” He called me the next day and he said, “What’s your book about?” And I told him what I thought it was.” He said, “No. It’s not about that. You need to write a book about how you’ve been successful because you have figured out how to drive really productive connections with men in a way that a lot of women struggle with, and that there’s real opportunity in that and that that certainly isn’t your only factor of why you’ve been successful or how you’ve been successful,” but that’s having watched me. He said, “As an outsider, I believe that that is like your superpower, and that’s what’s really helped you evolve your career in a way that many people don’t.”

      I went away, and I had always heard about the seven stories that get repeated over and over again. And people often attribute it to Shakespeare, but it’s not. But it’s attributed to all kinds of different people, but it’s basically like you can somehow boil down every possible plot, like book, or play, or movie, into one of these seven stories. And so I kind of liked that idea and I realized that throughout my career there was so many times that we’d say, “Oh! He’s the new John Smith, or he’s the new whatever.” And you start to see, there’s some danger and over-generalizing and stereotyping, but it’s sort of human nature to try to categorize so that you can understand –

      [00:44:07] CS: Yup, and to give people a shorthand. Yeah.

      [00:44:10] CVH: Yeah. And also like just to understand someone and where they’re coming from and what makes them tick and how they’re motivated. And I think part of it came to from me early on actually being quite terrible at doing this. And I remember coming home and being like really knowing I was right on something and going head-to-head with a very hard-headed sales, very loud and alpha dog-ish sales leader and telling my husband about how frustrated I was with it. He said, “You are overthinking us. We are very simple people, us men.” And so I think that epiphany point and realizing that it wasn’t enough to be right and that kind of taking the time to figure out how these guys were wired and what made them tick and then how they could be more successful given that wasn’t a bad thing. Like that that wasn’t necessarily selling out or that was just part of being effective of being an executive, becoming a leader, was being able to be more thoughtful about all of that.

      I felt like too as I started that I had stories to tell, like that for each of these types, there was there was a story to tell that would bring it to life. And to be honest with you, it’s kind of funny because, I sort of forced how you solve for X. I was like, “It has to be seven.” Like the seven story, that has to be seven. I kind of cranked out what the first seven were that came to mind thinking that that wouldn’t stand the test of time, but it seems to have so far. I’m sure there is an eighth type. I’m sure that there are a lot of people who are multiple types. But it’s been fun. I actually just gave a keynote on it. I hadn’t done that in a while, and it’s always really interesting. It’s a great way to get conversation going. Usually one of the first questions I always get are when are you going to write about the women types? And it is an interesting thought, but I’m going to stay away from that.

      [00:46:33] CS: Yeah, in your bio you noted, and we already talked about a little bit, but you’ve been involved in programs that help women find transitional housing and help get back on their feet. And so I want to talk about the hindrances to work across the board specifically here in cyber security of course that come from material issues such as housing instability or toxic home life or other massive disruptors that many of us thankfully never have to deal with. In working to hire more diverse candidates and more women in the industry, how does one factor in these difficulties and maybe even build them into the creation of jobs for people being held back in this?

      [00:47:08] CVH: Yeah. I just read some stat. I’m sure you’ve seen it too like just during the pandemic, not just in cyber, but how women have been particularly hard hit I think and left the workforce. I saw something like over 2 million.

      [00:47:21] CS: Massive. Yeah, massive.

      [00:47:23] CVH: Yeah. It’s so heartbreaking for me. That was really one of the main reasons I started [email protected] There were kind of two things. One was to help women figure out how to stay in the game during those difficult years when you’re really trying to have a family and kind of hopefully not just quit entirely and figure out how to do that in a way that works for you. And the second was to maximize your economic opportunity. How do you play your career in a way that gives you the most financially that’s possible around negotiating your salary and making different moves, because that gives you a lot of power?

      And so it is on the transitional housing front and the barriers. I’ve seen Mimecast do a lot of really amazing things during the pandemic and even more broadly to really help women stay in the game, whether it’s helping them navigate daycare. I think especially because I can’t even – My husband works as well. I cannot we said so many times in the first six to nine months of code that my boys are now teenagers. But if they were under 10, I don’t know what we would have done. It just would have been so chaotic. But I do think there are – it can just seem so overwhelming so to the extent that employers can really think about flexible work, can think about daycare support, can think about helping women transition into different roles during times in their life that help accommodate what they need, but you don’t lose them. So even though they may feel like they’re taking a step back like I mentioned earlier, or they’re treading water, it is so much easier. You’re still at least – You’re adding value, you’re staying current, and it’s in your whole scheme of your career. It’s actually a relatively short time span. And as soon as you want – What I’ve found in my situation and women like me who’ve kind of followed a similar thing and been able to hang on even if it’s in a form that’s a little ugly or messy for a little while. You completely end up back to where you should have been. Like I thought I would be behind forever, but I was immediately, I mean, within a year or two able to be exactly where I would have been had I never had to do that, and I’ve seen that with other women as well. That’s really heartening I think to realize that it’s worth kind of figuring out both on the employer side and the employee side how to sort of make it through that, like that part in your road that’s just you’re so squeezed and you may feel like it’s not worth it to spend all the money on day care and the pain of commuting and all of those things. But I think if you can just really – And if organizations programmatically can partner with their female employees to feel like that’s part of being a good employer and that it will pay off, I think we’ll end up in a better place. I don’t know if that answers your question, but –

      [00:50:45] CS: Yeah. Yeah, absolutely. This has been great, and just as we wrap up today, feel free, tell me a bit more about Mimecast. What are some project services or initiatives that you’re working on for 2021 that you’re particularly excited about at the moment?

      [00:50:59] CVH: Yeah. Mimecast is such an amazing company. Our founder and CEO, Peter Bauer, is really one of the most extraordinary people I’ve gotten to know just as a mind in cyber security, but also just as a person and the way that has built the company, the way he runs it, the way how thoughtful he is about our customers. I’ve never been able to work for an enterprise software company that cared about its employees and customers as deeply and genuinely as we do. And that really is a standard set from him and really permeates everything we do.

      Beyond that, like the backdrop of cyber and what we’ve all seen unfolding over the last – I mean, it’s an incredibly dynamic and difficult space to be in, but it’s been very much so or more so I guess over the last six months. And so that opportunity to help to really dig in to achieve the next level of sophistication and solving the problem the way it needs to be solved now, not the way it was solved a year ago or two years ago, is really quite exciting. And to feel like we’re in a position based on some really wise decisions that were made about our technology footprint and the way that our platform works around an interconnected global grid that enable us to evolve very quickly to solve the ever-changing problem in the way that it needs to be solved.

      And so part of that is overcoming the complexity that has kind of ensued around those – I was talking about those micro-categories of best of breed tech and seeing the opportunity to blur those lines to create stronger efficacy, to create kind of a stronger scale publish and subscribe model that thinks that thinks about not just email but this explosion of communication channels and collaboration channels with teams and OneDrive and Slack and all of these things that – And instantaneously you can be taking something whether it’s a bad URL or an attachment or whatever it is and it can just so quickly traverse across everything you have on your own, my own life, but then across the entire organization or into our supply chain. That’s what I’m excited about because it’s another Tetris that take us full circle back the ever changing Tetris that we get to solve.

      [00:53:46] CS: One last question, the most important of all. If our listeners want to learn more about Christina Van Houten, Mimecast, or [email protected], where can they go online?

      [00:53:54] CVH: My site is womenatwork.com, w-o-m-e-n-a-t-w-o-r-k.com. And Mimecast, just reach out to us anytime, mimecast.com. You can find me, and please feel free to reach out to me directly on LinkedIn if you’d like, or I’m always here for – I love the opportunity to give advice to women that are looking to get into cyber or tech or other things that they might be facing. It’s nice to be a wise old lady at this point and be able to focus on giving back as opposed to always just trying to figure out how I was going to make my own way. I’m excited for the opportunity to do that more.

      [00:54:36] CS: Awesome. Christina, thank you so much for your time and insights today. It’s a lot of fun.

      [00:54:40] CVH: Thank you. I really appreciate it. I enjoyed it too.

      [00:54:43] CS: As always, thank you to everyone at home or work for listening and watching. New episodes of the Cyber Work podcast are available every Monday at 1 pm central both on video at our YouTube page or at infosecinstitute.com/podcast, or on audio wherever find podcasts are downloaded. And don’t forget to check out our hands-on training series, Cyber Work Applied. Tune in as expert infosec instructors teach you a new cyber security skill and show you how that skill applies to real-world scenarios. Go to infosecinstitute.com/learn to stay up to date on all things cyber work.

      Thank you once again to Christina Van Houten, and thank you all again for watching and listening. We’ll speak to you next week.

      [00:55:21] CVH: Ciao! Have a great weekend. Thank you.

      [00:55:23] CS: Take care, everybody.

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