A dynamic, fun, and interesting conversation, you will enjoy hearing from Courtney as she shares about her time as a crypto linguist with the Air Force and her subsequent work in the national defense / national security industry. We talk about leadership vs management, the challenges and opportunities in COVID, and the value and importance of mentors and networking. Tremendous conversation you’ll enjoy!

Courtney mentioned Project Aristotle, here’s the link: https://rework.withgoogle.com/print/guides/5721312655835136/

Shout out to today’s sponsor, Veteran Executives Network (https://veteranexecutivesnetwork.com).

Aaron  00:09
So we’re going to jump right into today’s show bringing in Courtney Greeley. So Courtney comes to us from the US Air Force and she spent a career in the national security area of the world. And so I’m going to let her do all of the explaining for us. And I’m so excited to have her. Courtney, I just want to thank you so much for making time to be with me today.

Courtney  01:21
Yeah. Thanks for having me, Aaron. And thanks for all you’re doing for the veteran community. I think this is a great show and I’m excited to be here, so thank you.

Aaron  01:29
Awesome. Yeah. Well, it’s like everybody has, there’s so many different similarities between what people do, but then there’s so many different things. It’s a testament to the veterans community of how resilient and how adaptive and all the different areas of the world that people end up in. So quickly share with us a little bit about your background. So where are you originally from? Why did you choose to go in the air force? All that fun stuff.

Courtney  01:56
Yeah. So I mean, there’s some fun stories there I’ll keep them free. So I grew up little town right outside of Philadelphia. Go, Eagles. I was the middle child of three and my dad was a Vietnam vet and he was a Philadelphia cop by day. And then at night time it was all about war movies and stories and just a historian. So I grew up in a really patriotic family. I remember as a small girl, I wanted to be a Navy SEAL or a commando, you know, and at that time, my dreams were crushed when I learned women couldn’t fill those roles at that time. So I had kind of put that aside, went on in my school career. I was not the most… I wasn’t the best student in high school. I think I was focused more on the social aspects than the academics. And I say that because nobody was handing me scholarships when it came time for college.

Aaron  03:00

Courtney  03:01
Rightfully so. So I had to pay my way, right? My parents didn’t save for that. We were lower middle-class. So I knew that that responsibility was on me. And it wasn’t until I got to college that I really appreciated the educational aspects, especially when you’re paying for it yourself.

Aaron  03:20
Yeah, for sure.

Courtney  03:20
So, you know, I remember I’ve been at school a couple semesters and then another changing moment was we were in communications class. It was September 11th, 2001. And our teacher was running late. We were just carrying on conversation and then he came in very panicked and that’s when we learned about the attacks on the World Trade Center. And that shook everyone at that time.

And so right after that, a number of my close friends went into the service. And at that time, I had started off in college. So I wasn’t ready to make that pivot. And really, I hadn’t considered it at that time. But it was really exciting, going back to that time, how the entire country really rallied together and really felt united. I’d say it’s probably the most united I felt the country at any time. Everyone was flying their flags outside. Everyone was fighting against the common enemy which is always uniting. And so my friends went off to the military. My very best friend went into the air force. And so I would go visit her and I started to say okay. No offense to the other branches, we’re all friends here. But the air force had it altogether, right? It was good chow hall. Pretty impressive.

And so I continued on with school. But like I said, I was paying my way. So what I had to end up doing as my workload got bigger, I would have to take a semester off, work three jobs, you know, like 24 hours a day to pay for the semester and then go back. And I don’t have to tell anybody that was not sustainable plan. And so that’s when I made the pivot into the air force. And I remember it was really funny. So I get there and I’m like, I’m going to be a doctor. I’m going to tell them what I want to be. I sit down and worker’s pulling up the jobs and he’s like, well, I only have one job open right now and that’s working with nuclear weapons. And I was like, I don’t think anybody wants me working with nuclear weapons. I’m pretty clumsy. So I said, “What else do you have?” And he said, “Well, you could take this language test,” which is the Defense Language Aptitude Battery. Basically, it’s a made-up language. It’s a brutal test. You got to figure out the grammatical structure of this made-up language, et cetera. And I took that. I did well. So I went off and joined and I became a cryptologic Arabic linguist.

Aaron  05:56
Wow. That’s a mouthful just in and of itself. So let’s go back really quick. So we’ll forgive the unforgivable being a Philly Eagles fan. We’ll just pretend you didn’t say that. No, it’s all good. They didn’t have the best season, but you know.

Courtney  06:14
No, no. Still bleed green, though.

Aaron  06:16
Yeah. It’s all good. It’s all good. But no, it’s a fascinating story. So one, hats off to you. Because I know that you were hustling, you’re trying to make it work and trying to figure it out in college. And that’s an admirable thing to do. And, you know, especially in your situation where scholarships weren’t there, funding wasn’t there. You gotta go make it happen yourself. But then it’s also really neat. And again, thank you for sharing your September 11th story. Because it’s always fascinating interest to me of how people connect themselves to that day because we have like this pre 9/11 and this post 9/11 world. I mean, we had the post 9/11 GI Bill for crying out loud. But no, I think it’s a fascinating study of how that works.

You decided to take the DLAB. You obviously did really well there. And so you go that whole route. So what was that whole pipeline like? And then just kind of we’ll move through this kinda quickly but share with us a little bit about what you’re able to do when you’re in the air force because it’s not every day we talked to a crypto specialist especially on around languages. So share with us what you can about what you did and then a little bit of your transition story.

Courtney  07:30
Sure. Yeah. So the training program for that obviously is they put you through that battery because they need to get, you know, start off with people that have a level of aptitude to learn a foreign language. And then what you are is for Arabic, it’s a 64-week class where you are immersed in the language. Small classes, you have native speakers. They’re very, very, very intense.

Aaron  07:57
Did you say a 64-week?

Courtney  07:59
Yes. Yep. And to put it in perspective, you’re still treated like a trainee that whole time, right? Because you’re still in the training program. So it adds a little bit additional complexity, but I will say that just so much camaraderie there, and because I’ve always been stationed on joint force bases, so we had that fun banter across the different branches. I remember one time outside of the Navy’s barracks, they had an anchor, obviously. We painted it pink. And then one time, one of the new air force guys parked in the CO spot for the Marines. So a bunch of Marines came out, lifted the SUV and put it in front of the door so nobody could get into the air force barracks. So just fun stuff like that. It really did build a lot of camaraderie, right? This was a very difficult training. And I think at that time, the attrition rate was about 50%.

Aaron  09:01
Holy cow. Okay.

Courtney  09:02
And you’re talking about really smart people. And quite frankly, a lot of people because it is the premiere language school. They built their military career around making that part of the path. So very challenging. But I will say my best part about that school, I met my husband.

Aaron  09:20

Courtney  09:20
He was also an Arabic linguist. And so anyone that’s has been a linguist will also probably laugh at that because the defense language Institute (DLI) is also known as the desperate love institute. And I think that’s because the training is so long, everybody just gets together. And then from there, you go on. Once you graduate from there and you hit the fluency benchmarks, you go on the intel school, right? And that’s in San Angelo, Texas. That’s also intense, very long days. And I had also had my first child during that time as well. So it was, you know, just like all veterans, right? A lot of grit and tenacity to get through and continue on with success. So then from there, what I did, went into – obviously, a lot of it is top secret/SCI-classified went on and I was stationed at NSA Georgia, and so supported joint missions there.

And really, in terms of what I can say, we were supporting the front line during Operation Iraqi Freedom and Operation Enduring Freedom, right? So providing that frontline support. There were times, it was really, really stressful. Because for anyone, if you ever got lyrics caught in your head incorrectly, you can’t unhear them. And so when you’re translating real time Arabic, not only are you translating from Arabic to English, but then also the cryptography part of it, right? You’re then deciphering codes that they’re using and building out patterns and that target analysis as well. So there’s a lot of stress there and really a lot of duty and responsibility to make sure that you’re getting things right and providing good, accurate information. So that was in Georgia. And then that’s where I ended my air force career.

Aaron  11:28
Okay. Wow. So then take us through that. So take us through the transition story and then how that led you into your first one or two roles afterwards.

Courtney  11:39
Sure. Yep. And I’ll be completely honest. And this is where I was really excited to come on this show too because I think that the whole transition programs are a bit lacking. I remember sitting through TAP class and they’re teaching you how to write a resume, how to do some of the mechanics, but not really the things that are going to get that return on investment, right? Like the networking, really understanding companies and research and things of that nature. So what I did is, as I was getting out, I would have stayed in for the career. But the dynamics of my family, I had to move closer to home, which is Philadelphia. And I couldn’t get the Fort Meade station at that time. So I got out. My husband, followed him. He started his career as a financial advisor and I stayed home with our son and finished college degree. Thank you, GI Bill.

So I finished my degree and my clearance was going to expire. So I decided to just go to a job fair down in the DC area. And I knew I didn’t want to be a linguist anymore. Just again, because I had done my part, but there was a lot of stress around that. And it’s crazy schedules as well. I don’t have to tell anyone, you know, the different time zones. When things are active, it’s night time here. And that’s when all the fun stuff happens. So I was given an opportunity to work for – it was a small defense contractor and they were going to put me in a role that was working on the actual building of the systems, the SIGINT systems.

So I got to do that. I was really blessed with a lot of great mentors along the way that were willing to teach me anything, but I will say, I asked. Teach me this. I want to learn more about that. Just very curious. So I got that experience and because of that, I was really key to a follow-on proposal. The company I was working at wanted to bid on the follow-on work as a small business. And just like in any sales role, customer intimacy is key to be able to effectively respond. So I moved into –  that’s how I made that pivot into the business side from the technical. And we won that and then move right into standing at the operations to support that contract. And from there, again, I had really great mentors along the way. But I will say I always fought for the next position, right? I would, you always have to be –

Aaron  14:17
How so?

Courtney  14:17
You always have to be thinking a couple steps ahead and always kind of mapping out. Okay. So if you look two steps ahead and what do you need to be successful in that role from a skills perspective, from the tangible and intangible, what do I have to do to get there? Who do I have to work with? Who can I learn from? And so within the same company, I moved into our advanced cyber operation sector. I had previously been an enterprise IT and my boss at the time, and I won’t say his name because I don’t want to embarrass him, but it was a choice between two positions where I could have a director role in one organization or work in a bit of a different role operations for another organization. And based on titles, you might say, okay, well that looks like it’s a step backwards. But in communicating with that senior VP there, he was going to teach me all the things that I knew that I was lacking. And so that, to me, was, yeah, that was more valuable. So I went there. And then from there, I mean, I was just hungry for everything operations, organizationally. How do you better serve your customers? I like the technical side. I like the business side. I like the strategy, the tactical. It was just all together and so I really started to progress down that path of honing those operational skills.

Aaron  15:49
It’s quite the journey that you were on. So, I mean, here you are in this super technical, very specialized role, TS/SCI, this, that, and the other. And you’re working these crazy hours. You’re right. You’re supporting OIF and OEF. So yeah, it doesn’t take a rocket scientist figure out the time zone change and what kind of impact that had to your personal life and the stressors involved in that. So I can only imagine what that was like for you, but then to come out of that. And so at the time, you weren’t like the cybersecurity guru, but over time, you’ve applied yourself, you’ve worked really hard, you’ve networked. And so talk to me a little bit more about the importance of mentors. Because I feel like that is such an understated aspect of transition. And it’s something that I feel like once people embrace it, it’s like the secret weapon. So share with me a little bit about your experience when it comes to mentors.

Courtney  16:45
Right. Well, it’s actually a really great point here as well talking about that path. So I’ve had great mentors along the way. I’d say earlier in my civilian life, I worked really hard and I had people that came to me and wanted to mentor me because they saw the level of effort being put in. Because at that time, I also didn’t realize the value of a mentor. So I had people that got out and more proactive and said, “I want to see you be a success.”

Aaron  17:17
That’s cool.

Courtney  17:17
And so that was how that start. And then once I realized how valuable that was in transitioning different roles, that was something that I then went after proactively. So while I was at my last position, I had gotten involved with one of the local groups here in the Fort Meade area and it was called Rising Stars. And there was one woman there and I will say her name, her name was Doreen Hardwood. And she had been within the NSA. I’d worked with her very indirectly. She was high up and I was kind of down here doing the work and I always really admired her. She got stuff done. And so I saw her at this event and I sought her out and said, “I know there’s some mentor pairing that has to happen, but I want to expedite that, like, can we meet?” And so she ended up becoming one of my mentors and really, really, that’s when I saw like the magic of it.

I came to her at one point and said, “Hey, I’m looking to transition. I think I’ve done everything I can do here. I’m looking for what that next step should look like.” And at that time, it was funny. I had a couple options and I was really looking for her to tell me, go through door A or go through door B. What she did is added a twist in there. And she said, “Hey, I was talking to one of my good friends and they have a position open at this company called IronNet Cybersecurity. I think you should talk to them.” Well, I didn’t want to be rude. I was familiar with IronNet Cybersecurity. That was General Alexander’s, you know, former DIRNSA. That’s the company that he started. And working in the same circles, I knew a bit about what they did. But they were more on the commercial side and that was not on my radar.

So out of respect, I went ahead with meeting and it was like all these light bulbs went on. Everything that I was hearing about the work that they were doing and how they were applying what they learned – really, what he learned at the NSA and taking those tools and him having a different perspective on the gaps that existed between public and private sector collaboration, it was really exciting. So here I got thrown a loop, thanks to my mentor. And it was a game changer for me. I went ahead, took that position and outside of joining the air force and marrying my husband, of course, it was the best decision I’d ever made. It really just opened up a whole new world to me of going from military, defense contractor to leveraging all of that and applying that to the commercial space.

And then there also, because I knew the value of a mentor, you have to seek them out. So there would be people – I’d start to watch across the board, inside the organization and outside, for people that I knew could challenge me and help take me to that next level and seeking them out and being intentional with that time and not being bashful. You’ll find most people want to help you, but you have to help yourself as well, right? You have to come to them with an idea and not just this blank paper of help me, help myself. You have to make those connections.

Aaron  20:42
And you’re making so many points right now with that because it’s like, there is this expectation and I don’t know where it comes from. It’s like this whole – it’s going to sound so bad, but the whole military discount type mentality, like, hey, you owe me this or something. And I don’t subscribe to that, by the way. So let’s just make that clear. But your point about mentorship, I think, is spot on. And I wish we could yell this point out because you have to go proactively seek this out. It’s not just going to show up on it. It might every once in a while show up. But I mean, you’re a good example of that, right? You had someone who really wanted to help you, but that is definitely the exception, not the rule.

And if you’re wanting to advance in your career, or there’s certain things that you want to go do, you gotta be strategic, you’ve gotta be thoughtful. You’ve gotta be a little bit proactive. You may have to put yourself out there. But like you’d said, people generally are really interested in helping others. And using a little bit of intuition, you can kind of tell who those people sort of are, so you kind of filter them out beforehand. But I just think it’s a really cool story. And you’ve already said it just how impactful it’s been to your career, but I cannot – I just want to continue to hit this point hard because so many people could really hear that, could really use to hear that because there’s so many opportunities. I mean, has that been a continuation? So tell me where then from there, where you are now, what does that mentorship situation look like for you?

Courtney  22:24
Right. And that’s a great question. And I think there is a bit of strategy there too. So I’ve now moved into the role. You know, you’re a student for so long and then you have to also be the teacher. And so I’ve moved into a role in my career now where I’m also mentoring informal programs, formally and informally. So with the WiCyS, which is Women in CyberSecurity, great, great program, they now are international. It was started out in Silicon Valley, had some backers. They have big sponsors right now. Facebook, Palo Alto, Google, you know, you name it, Target. There’s a lot of people that sponsor that organization because they really believe in the mission. And so what WiCyS has done is they’ve set up this mentor-mentee program. And so that’s the formal program that I’m in in terms of a mentor. But then also I signed up to be a mentee because we can always learn, right? And so it’s fun to see both sides of that.

But what I will say, as I’ve learned and moved into the mentor role is that, again, you really have to help people help themselves. Or you’re not giving them the answers. You’re giving them enough direction to go find some information, come back and then helping kind of coach them through those decisions. But more than that too is when you get a mentor, you’re expanding your network, right? They become an extension of your network. And when they see that you’re going to work hard and that you’re in it, and you have skin in the game, they’re gonna match you with that. And they’re gonna want to see you succeed and they’re gonna feel vested and they’re going to want to reach out to their network to make sure that if there’s a connection, they can make that.

Aaron  24:21
That’s true. So what you’re saying, you gotta be a good mentee as well.

Courtney  24:25

Aaron  24:25
You gotta be someone who’s going to be willing to take coaching on board. You’re going to be engaged and not just sit back and expect to help chart your whole life’s situation out for you. It doesn’t work that way.

Courtney  24:40
Right. Well, that can leave a bad taste in people’s mouth too. I mean, the reality of it is though it is a small world and we tend to roll in the same circles and people communicate that information as well. The good, the bad and the ugly. But what I will say, too, staying on the mentorship track is that one of the really cool, good news stories from 2020, we always hear about the bad. I think a lot of good came out of 2020 as well, and that’s not to discount anybody that’s suffered or had losses, but really to be balanced there and see the good. I will say the accessibility to mentors is, I mean, it’s at an all-time high because people are still home. And instead of feeling like you have to schedule a lunch date down in DC to get to know somebody, everybody is willing to hop on a call. And so the accessibility factor, it’s something that people should be taking advantage of this time.

There are challenges in terms of networking to find those mentors. But really, again, we’re in the age of information, it’s easy to do some background searching, find something out, find somebody that you’re interested in being a mentor. If you don’t have access to mentors where you are currently, do the research and find them. I always say, too, as people are making that transition from the military into the civilian world, and I’m talking now from an audience perspective, I’m talking to people that have been in the military, not like myself for a couple of years, but really that either have retired or put their 10, 20 years in, as you’re making that transition, start to look at – I always look at the top and work down, right? So it helped me in my path, as I said, where do I want to end up in the C-suite, which of those do I identify most with? And then working backwards from there. And it doesn’t mean that you’re going to end up in the C-suite. You certainly can, but it starts to give you that kind of backwards career pathing to understand where you want to invest your time. And that will help you also identify which mentors that you want to go ahead and seek out.

Aaron  27:09
Rewind 30 seconds, hit play and listen to that again. So that was solid, I would say. I mean, that’s great, great advice on how to kind of map out your path and then put a little bit of thought behind each step along the way. And I mean, that’s brilliant. Absolutely brilliant insight. So when we come back from break, I would like to transition a little bit more into a topic that you broached just a few minutes ago about Women in CyberSecurity. I would love to understand what is that like because there’s not a ton currently, and that’s something that’s growing. So I’d love to learn more about that. And then I’d love to learn more about some of the leadership challenges and some of the leadership triumphs that you’ve had over the last few years.

Courtney  27:58
Sounds good.

Aaron  27:59
Awesome. So this show is made possible by some of our amazing sponsors, and so I’m incredibly grateful now that the Veterans Business Podcast, we are accepting sponsorships and so I’m incredibly excited. And our first sponsor that I would love to promote and would love to thank is the Veteran Executives Network. So Veteran Executives Network, it’s network that I’m tied very, very closely to. It’s a group, it’s a network that is being formed currently. It’s in development. You can find more about the group on LinkedIn, but it’s a place where veterans can help each other, do business with one another, whether it’s private sector, whether it’s public sector, there’s a ton of opportunities. It’s in development. So I would encourage you to reach out, start on LinkedIn. You can also go to veteranexecutivesnetwork.com for more information. But incredible opportunity. And I think it’s a great way for veterans, for us to team and partner together to advance business. There’s so many synergies that we can realize if we were just to take a quick second, pop our head up and maybe work together. So check them out. Again, grateful for the sponsorship.

So Courtney, again, just want to jump right back into where we left off. So Women in CyberSecurity, that’s a new topic. Cybersecurity obviously has been a male-dominated space for quite some time. So share with me from your perspective, what that journey has looked like for you.

Courtney  29:19
Sure. And I think the reason for that, it’s nobody’s fault. It just started, I think, with the education and providing more opportunities earlier in that cycle for everyone, really. When we talk about the reason why there’s such an emphasis on Women in CyberSecurity is because the numbers, the data backs it up, where when you’re looking at jobs, the gap there, and I will say that it’s closing, so we’re making a lot of really great progress to do that. And it’s not saying that at the end of the day, we’re trying to see the numbers be equal, right? But to make sure that we understand why there is a gap and seeing if we can address that, right?

And what the research has shown over the years is that, again, starting off in earlier education, providing more opportunities and getting that excitement for STEM programs started earlier in the process. And so what we’re seeing is that there are now, like I said, that gap is closing and it’s because there’s a lot of great programs out there. What WiCyS is doing, and right now, there’s a lot of affiliates. I’m on the board for the Critical Infrastructure Affiliate. The Critical Infrastructure is a huge part of cyber. And so instead of having a locale, we service really the whole world in terms of people that are wanting to understand how to work within cyber and what are the issues affecting critical infrastructure at this time.

So what we do, and it’s interesting having worked there, started there during the middle of the pandemic but really learning a lot and understanding that audience and what they’re seeking out. And what we’re seeing is that women, and we just talked about networking and mentors, that they don’t see those positions of where they can find other women to connect with. Because the reality of it is we all have unique challenges. And so having those women in leadership positions and along that career path, that people that are curious can ask questions of is really important and understanding what I get a lot of questions about is, well, how do I get into cyber, right? And so being able to help pull out some of that information and help them understand, well, you know, cyber covers a lot, right? It’s very broad. And I mean, you can talk about the policy, or you could talk about the technical aspect, and then each of those really branch off into their own specialties. And so helping them understand and get some education really on is really important.

And then when we’ve talked to women that are later in their career that want to make that pivot, that’s a little bit of a different discussion. Getting them access to resources. One of the greatest things about WiCyS, and is a nonprofit, is that we have a lot of companies that are reaching out, providing free training SANS, trying to help, like I said, provide those resources that women that have those capabilities can get into the field and get there just a little bit easier and have equal opportunity. So I would say to this group to check that out. And it’s not just for women. We have a lot of men that are active in the community as well.

And for the veterans side of it, they have then also classes for veterans as well. And I think membership there is really cheap, especially for veterans, but it’s a great program to check out. A lot of resources. And then really just community, right? Sometimes we don’t know who to ask questions of despite having access to so much information at our fingertips.

Aaron  33:22
That’s true.

Courtney  33:23
We want to be the person to help talk you through that. And so we really try to bridge that gap and reach out and be that community to support people. And it’s a very supportive community. So it’s exciting.

Aaron  33:36
Do you see – when it comes to women asking you these questions about getting into cyber, is it principally around cybersecurity technical roles or is it more policy-driven and then what is the general path? And not only just applies to women, just for people in general that are looking to transition to a career related to cyber, whether that’s cybersecurity or infrastructure or whatever the case may be. What do you see being some of the first stepping stones for people, especially those that used to have a security clearance and it’s expired and they want to get back into it, how does that whole thing work?

Courtney  34:10
Oh, the clearance. I’m not going to talk about the clearance thing. That is a challenge all on its own. We’ll see if it’s expired. But if I could just back up to the other question.

Aaron  34:20
Yeah, for sure.

Courtney  34:21
Right. So typically, when I’m getting asked that question, it is more on the technical side and I think that’s because – again, that’s what they associate with cybersecurity. And so it’s helping them on that journey, understanding start to look at jobs out there. Go search a job board, start to see, you know, understanding the what. What are the different paths, right? And then I would argue, if you’re going to go down the technical path, what I tell a lot of people, and this is just because I’ve seen it firsthand, is starting off understanding like some basic inner workings of computers and really networks, start to understand what is happening in networks, right?

A lot of people want to jump, they look at certification paths and they want to go right to Security+ (Plus), and I say, just stop and go back, understand the network. If you’re on that certification path, look at Network+ (Plus), right? Because you’re not going to be able to defend something that you don’t understand how it works, right? So that’s kind of like 101. Outside of that, there are so many great free resources online where you can start to just get a taste of different things that you want to do, right? Do you want to do, you know, there’s things like pen testing and then there’s flavors of that. You can go – there’s lots of courses online. Udemy, I think, has a lot of free courses, Coursera, Codecademy. There’s all these different pieces that you can start to dabble in those.

And so I would say that start to look at jobs that are out there, start to understand what they’re looking for and which ones get you excited. Because otherwise you’re going to start to put like a, you know, what is it, don’t put a square in a circle, whatever. You’re going to go the wrong way. Look at things that get you excited because once you’re excited, especially if you’re a later learner, I mean, the reality of is learning is more challenging especially with the demands of life. So find something that gets you really excited. And if it’s policy, I mean, obviously policy is huge right now. Especially as we have a change in administration, start to dig into that. We just had an executive order that was put out, start to decompose that understand what that actually means. Not only just at the state level, at the national level, at the international level.

And like I said, just start to piece those apart, and really whatever gets you excited, dig into that more and then find those networking groups. There’s so many out there. I would say that the community overall in cybersecurity is really welcoming and people really want to help others get into that field. So there’s no shortage of opportunities to network and find resources. But you, going back to the earlier comment, you have to come with something on the paper. I can just show up with a blank piece of paper and say, “Tell me about cyber.” It’s going to be really challenging conversation. You’re not going to get all the value out of it.

Aaron  37:28
Well, it’s like the conversation of the veteran or where someone’s getting out and you want to help them. And you’re like, all right, man. So what do you want to do? And where do you want to go? I’ll go anywhere and I’ll do anything. I’m just like, come on, man. You gotta help me out here. So kind of the same rules apply when it comes to cyber. Like you’ve got to start to of kind of dabble and kind of get a little bit of a smattering of a few different things, whether it’s cloud, whether it’s pen testing, whether it’s security, whatever. There’s so many different places that you can go with that. And so it sounds like, just do your research, tinker with it, play around. Like you said, there’s so many resources that you can get a pretty good sense of what that’s gonna look like and then job boards and then networking again.

And what’s so cool about networking, too, is you could go – and this is like solid advice that I’ve heard from several people. And even if you’re not looking for a job but do informational interviews with people. So it’s like set the table first and let them know like, look, I am not trying to solicit you for a job. This isn’t like a secret sales pitch. I just want to get to know you. I’d love to learn more about your career. How did it work? What’s some things you’ve loved? What’s some things you hated about it? What’s some advice you’d have? And in the process, you’re doing a couple of things. You’re picking up a mentor, possibly, whether you realize it or not. And then two, you just never know you do enough of those. And they find out what you’re all about, what you want to do. They’re like, you know what, we’ve got an opening at our company. Or, you know what, my buddy over here working over here has a position that would probably be a good fit for you. And so it’s just really good advice.

I wanted to kind of transition our discussion then into – so there’s a few things here. One, you assumed a role with a company in the middle of a pandemic, so that’s got to be kind of fun. I would love to hear how that whole thing went down and then tell me what it’s like then be a VP of operations. What does that look like for you?

Courtney  39:27
Right. Yeah. So you noticed that. Yeah, that was interesting for me too. And it was really just… it was an organic transition. So I had been at IronNet some time, learned a ton. That entire company, every person there, super talented. I said it was like the West Point of companies. Everyone was at the top of their game and it was exciting to see how that dynamic really makes everybody better. So nothing but wonderful things to say about IronNet and their mission. It was just for me, there was this feeling of I’m ready for the next thing. And so going back to full circle, I went and reached out to my mentor.

Aaron  40:16
Boom, there we go.

Courtney  40:16
And I said, what I had said is I was early in this process. It was just this itching feeling. And I couldn’t shake it. And really I’m very – a lot of my decisions are based in faith. And so, you know, I really felt like God was just poking me and saying, “I need you to explore this.” So finally, I was like, okay, okay. So I reached out to a – to me, it was a third party of someone that knows me really well, a former boss. And I just let him know. I said, “Hey, here’s some things that I’m feeling. I need some help thinking through this from an objective perspective.” So we talked through some things, and at the end of the conversation, he said, “I’ve been talking with this other CEO and I think you both could fit well together. So let me set that up.” And really, I didn’t know what that looked like. He knew my skills and he knew the CEO and the company. And he saw something that I think we didn’t see.

Aaron  41:13
That’s cool.

Courtney  41:14
So we had a conversation. And at this time, I had started exploring other opportunities and entertaining some other offers. So I started to get a feel for what I really want in that next step. We had our conversation, and it just was… I mean, it’s just we clicked. And I want to pause there for a second because I think it’s really important to foot stomp on this one lesson that I had to learn over my career was be you. You have to be yourself. I understand that when you have interviews or you’ve reached out to somebody because you’re interested in their job or you’re interviewing or trying to find a mentor, don’t be anybody but yourself, right? Because eventually, that’ll come out if you’re putting on some sort of like, you know, we all wear a different kind of masks sometimes. But in those moments, especially early on, you have to be yourself because if it’s not going to work, it’s not going to work and figure that out sooner than later.

And so I remember his name was Greg Virgin. We had our first call and we were both just very transparent on here’s what I’m good at and here’s what I’m not, here’s what I’m looking for. So we continued the conversation, and every time we met, we met a couple of times, it reinforced that. And where I really saw some magic there, going back to diversity, was we were very complimentary in our strengths and weaknesses. And I saw that as being really exciting. And his company, the company RedJack at a time was at a place in their growth trajectory where all that I had learned over the years, and I called them like legos of information, slots I’d picked up along the time, I could see the building now and see how all those fit together. And so at that point, it was really a no-brainer. And then when I let IronNet know, they understood. You can’t really keep people back from growth. And there wasn’t an opportunity there at that time. So it was very amicable and moved on into, transitioned into RedJack.

And I will say, I love people. So I think it was like a couple of days before I started, and all of a sudden I realized, I said, what am I doing? I’m starting a new job in a pandemic. And like, I’m not going to meet this team in person. But all that aside, it was unfounded fear and the team has been really great. And thank goodness for technology. I feel very close to the team right now. So that’s been good. And it’s important because especially when you’re in a leadership role, trust is paramount. And it’s difficult to build that trust if you can’t look people in the eyes. And so we’ve been able to have those conversations and it’s been really great.

Aaron  44:11
That’s awesome. That’s great. Yeah. It almost relates back to the point you made earlier with the accessibility of mentors. And so we’re all at home. We’re all working out of a home office, like a large majority of us are. And so there there’s a greater accessibility to people, but it gives you, as a leader, an opportunity to really speak life into your team and to get more connected. And not that there was any excuses prior because there shouldn’t be, but now. there’s really no excuse to be able to get together with people and really connect with them. Whether you’re geographically concentrated in the same area or you are spread out the country or across the globe, there’s so much more access to people now. And so it’s fascinating. It’s fascinating to do the whole getting hired in a pandemic. So you didn’t have a building to go to on day one, I’m guessing.

Courtney  45:06
No, we did not. I did not. So it was a little anxious. But my first, when I got there, and I had asked the CEO, I said, “Would it be okay with you if I in those first 30 days really set up one-on-one time with each employee” primarily just to get to know them as people, right? And I wanted to ask for permission because there’s a lot of goals that we have and really those first 30 days consumed a lot of my time, but it was time well spent because at the end of the day, you know, you have to be – the people are what make any company their core differentiator. And so understanding them and knowing what their personal goals are, professional goals and what they need on those different levels are really important. And really, it’s driven, I’d say, so I’m still within, you know, I think I just passed maybe my 90-day mark, but it has really driven the remainder of those strategies to really work and prioritize around the employee base.

And you asked a question earlier about leadership and challenges there. And I would say, I mean, it really goes back to the basics to be a great leader. Like you can’t fake caring for people, right? And so in that job, where leadership is different from management, like you’re really trying to build those people to the next level and do things to get them to the next level, remove their obstacles out of their way, get them the development that they need, really that coaching and really their success is your success. And you can’t do that unless you have things like –  really, especially during this time, being empathetic.

And I think Google did a study, they did a co-work study trying to figure out what really makes highly productive teams. And so I think it was a two-year study and I’m kicking myself because I can’t remember the name of the project. But one of the outputs of that is they’ve realized that people are more productive when they feel safe in an environment, right? And I don’t think that’s any shocker here, but it really reinforced that as leaders, we have to empathize with people. So, if someone’s not getting something done or you’ve seen a change in their work productivity levels or behaviors or attitudes, really taking a step back and seeing them as a person, or like try and putting yourself in their shoes and understand what are the challenges that they have. Right? And being there to help them. That, to me, is paramount.

Aaron  47:52
I just looked it up, I think. Is it Project Aristotle? Was that right?

Courtney  47:57
Yeah, that’s it.

Aaron  47:58
All right. So I will link this up in the show notes for people to read. There’s quite a lot of articles about it. Yeah. And you just hit on a topic that’s near dear to my heart and I get really, really amped up when people mentioned this. And so I’ll share with you a little bit about my perspective on it, but I’d love to get yours as well. And so leadership and management, right? So often in the military, because I think it starts in the military. We get fed this perspective that your rank equates your leadership responsibility. And I’m trying to say this the right way without putting my foot in my mouth and having to edit this out later.

Courtney  4846:
Well, that’s an option.

Aaron  48:47
Not really. I’m trying to do this in one take. So even all this right now is staying in. But what I’ve noticed, I’ll just fast forward to kind of what I’m thinking. And then maybe I can back up into it. So what I’ve noticed is leaders are the ones who actually give a crap about people and the organization in terms of the wellbeing and the care of their people and how they’re advancing towards a common goal, whether that the individual goals of that person. And guess what, it may include not being at that company. It may include going into something else. But that’s leadership at its basic, at its foundations for the individual person. And then you’ve got leadership as it associates to the company of like getting people inspired and rallied around a vision and a purpose and the why behind the work that they do and why it matters and why it’s important. Leaders help instill that. Versus managers are dealing with deadlines, tasks, or task masters, or masters of organization and delegation of things that need to be done.

And I think so often, and I may have jumbled some my words there, but what I have found is that those two things are not synonymous. And I know it sounds obvious, but they’re not. And I think so oftentimes we equate them to be the same thing. And so we have people that are in “leadership” roles of a company, but really, all they are freaking awesome managers, like really, really gifted managers, but they’re not leaders. And so we’d love your feedback on that. Do you think I’m crazy? Do you have another perspective? What’s your thoughts?

Courtney  50:29
No, I think you’re absolutely correct. And I like how you said that they’re awesome managers, right? I think part of that comes with, you know, there has to be some introspection as well, and really, there are tools to help with that, right? There’s all those personality tests out there, but one that really impacted me as a leader, it’s called DISC. Don’t ask me what it stands for. I was getting ready to go to leadership training. And about a month out, we got this quiz. I took it. To be honest, I completely forgot about it. So then we show up for training and day one, and the woman comes around and hands us a booklet with our name on it. And here it was the analysis that was done on the test that we took. Well, I’ll tell you what. I opened that book. And I was like, okay, I was expecting the same feedback you usually get. And then I took the book and I held it closely to me because this assessment saw deep inside me. Like it was telling me things that I knew about myself, but I don’t think I ever really knew.

Aaron  51:36
Oh, my gosh.

Courtney  51:37
It was really wonderful because it helped me understand where I had some deficiencies in regards to how I view leadership as well. And so there’s those resources out there where you can start to get an assessment of where maybe you have strengths and weaknesses, and the same thing for your team. I think continuous leadership training’s really important as well. Because we can sometimes, you know, again, we can lose sight of that. And so having that constant focus back on people and the vision, just like you said, that’s so important. The why. What are we doing every day?

At RedJack, we just started rolling out OKRs, which are objectives and key results. And that’s really exciting because it gets the team focused around a common mission and it helps everyone understand how they’re contributing to moving things along. And then it’s really clear what a win looks like and everyone can celebrate that together. And so we’d been really big on helping people understand the why behind everything because that’s really what’s going to get you through some of the lower times, right? There’s peaks and valleys. And so understanding what you’re doing and how it’s impacting the overall mission is really important.

Aaron  53:00
For sure.

Courtney  53:00
Yeah. I agree. I agree.

Aaron  53:01
For sure. No, that’s pretty awesome. And so genuine curiosity if you remember from the assessment, so which type were you, D, I, S or C?

Courtney  53:14
So I will say every time I take these tests, they’re like, oh, well, we’ve never really seen this before. You’re kind of like a little bit of everything. But it was interesting. I thought I would be more, again, I think D was dominant. But I was actually more on the softer side than I’d realized. I’ve always been a very direct communicator. And so I think I had this idea of myself that was a little bit different than what I actually was displaying in my work. And so it helped me understand how I can adjust my communications. But really, again, hitting on that empathy. I think earlier in our careers, we’re doers, right? And we’re rewarded based on how we accomplish things by deadlines. And so there is a transition that happens when you move out of that, then you become a manager, right? And understanding what those skills need to be.

Aaron  54:09
And then – oh, sorry.

Courtney  54:11
Go ahead.

Aaron  54:11
No, it’s like you just triggered a thought there. So it’s like it goes back to the point you made earlier. So I just want to reemphasize a point that you’ve made when it came to wearing masks, so to speak. And so one, like in the military, we may have this tendency – or maybe it’s truer in the Marine Corps. I’m not sure how it is with other branches. But there can be a tendency to reward those that are incredibly brash to the point and will beat you up, crack you upside the head to get done what needs to have happen, right? And then there’s this, I mean, you articulated it very, very well. I don’t think I’ve ever heard it articulated the way that you laid it out, which then when you get out, then you’re really good at tasks, right? You’re like a really good task manager, or you’re really good at working through a project, you’re really good at getting stuff done.

And then over the course of some time, then you begin to find yourself transitioning into a leadership role because you start to kind of – it’s indicative of the tests that you took, right? So you thought that you’re probably going to be a D because that’s kinda what you were told to be. That’s kinda what you thought you needed to be. And you may have even adapted some of those traits just to fit in or just to be able to adapt to your situation. So you’re as effective and as efficient as you could possibly be. I mean, I think a lot of us tend to do that and until we get away from that stuff, then we allow –  it goes back again to another point you made, which is being yourself, allowing yourself to just like, it’s going to be okay, just relax, be who you are and let that shine through. And then you don’t have to fake it anymore. You may not have even known you were faking it. It’s like one of those things  where you’re like, man, have I been acting this whole time? Do I need an academy award? What the heck?

Courtney  56:04
Especially for women. I think I’ve been really fortunate to be in great organizations where I didn’t really see that. I, quite frankly, never really paid much attention to the gender roles, right? And any type of gaps there or deficiencies. And so I was fortunate in that regard. And then, especially when I was doing hiring, for the NSA, we just want the best. So we never even took that into consideration. There was no special pay for women versus a man. We just gave the salaries that fit those skillsets. So I see that. But then as I started to progress in my career, you start to see it a little bit, that there were different skills that men were displaying, right? And so you’re like, okay. And again, looking at those that C-suite, well, I’m going to start to mimic that, right? And some of that didn’t feel as natural to me.

And so there was a period where I think I was trying to be something that I wasn’t, just being completely transparent, and feeling like I had to be more aggressive and I had to be more of this or that to really fill that role that was maybe a male-dominated role. And then when I stopped. And again, going back to mentors and having people, a community that really encourages you, and when I stopped and said, “That just doesn’t feel right to me. And if that’s what it takes, I don’t want that.” Once I accepted that, and I could be myself, it doesn’t mean that, you know, there’s a time and a place for everything. The jokes that I might have in a smaller group where we’re maybe teasing each other, I’m not going to do that in the boardroom, right? And that’s what I mean there’s a time and place, but always being authentic to yourself too. It’s really important.

Aaron  58:00
Yeah. Well, that’s really well said. And I just realized like, holy cow, time has flown and we didn’t even get to some of the stuff I was really wanting to get to, but this has been fantastic because I feel like there’s a lot of really non-tangible, intangible things that we talked about in the last little bit with each other. And I think there’s a lot of great lessons and great nuggets to be plucked out of this conversation for people in terms of how they navigate their career, how they treat each other, how do they progress? What are some things that needed that need to happen? And so I think it’s been terrific. I mean, I’d love to give this last segment back to you. If there’s anything else that you’re just dying to get off your chest, this would be the time to share it. Because yeah, I cannot believe this. Time has flown by.

Courtney  58:47
Right. I would just say, it’s important that as you’re seeking out and growing your career to always give back. At any stage of your career, you’re going to have an experience and a story to tell that’s going to help somebody else. So even if you’re early out in your career and you’re like, well, I can’t be a mentor, you can. You can be a mentor to college students, right? There’s always a place to give back and making sure that you’re keeping community at the forefront of that is really important. And that’s really what makes the world go round.

Aaron  59:17
It’s awesome.

Courtney  59:17
So thank you. Thanks for your time. And thanks for having me on. And again, thanks for all you’re doing. I think it’s wonderful and I think it’s really needed.

Aaron  59:25
I appreciate that. No, this has been a lot of fun. Thank you, Courtney.

Courtney  59:28

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