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EPISODE 81
How to Negotiate a Pay Raise with Edward Skipka

HOW TO NEGOTIATE A PAY RAISE WITH ED SKIPKA

About this episode

In this episode, we listen to Kip and Ed go over how Ed managed to get a 25% pay raise in a very short period of time and the whole details of his situation.

Edward Skipka, a vulnerability management analyst, goes over his experience and how he managed to double his pay in just over two and a half years. He highlights that doing your best and solving problems can take you to another level within your company.

Kip mentions how some skills, like curiosity, can’t be taught and that people with such skills are able to progress in their careers much faster than they think.

You will also learn how important it is to leverage yourself in your current position, how to be able to not take anything personally, and how to know your value and be able to get paid what you’re worth in the industry

What you’ll learn

  • Can you get into cybersecurity without a technology background?
  • How to make yourself valuable to hiring managers and recruiters
  • How to leverage your position to get paid more

Relevant websites for this episode

Episode Transcript

Kip Boyle:
Hi, I’m Kip Boyle and today, welcome. Well first of all, welcome to Your Cyber Path and glad you’re here. Today I’m actually here without Jason Dion, who’s my regular cohost. But Jason’s taking a well deserved vacation and so I hope he’s having a good time in his time off. But the show must go on. So today is we’re doing episode 81 and it’s called How to Negotiate a Pay Raise and we’re going to learn how Ed Skipka negotiated his pay raise. Now you may remember Ed, if you listen to episode 58, which was called How to Get Hired with No Experience, which was another thing that Ed did. He’s a bit of a superhero, right? So he got a cybersecurity job with no cybersecurity experience. Then he went on to negotiate himself a really great pay raise. So when he told me that, I was like, “Ed, you got to come back and you have to tell the audience how you did that because I think that is incredibly motivational when you hear somebody actually tell you how they did it. Can really unlock doors that you thought were locked to you.”

Ed’s previous episode with us again, that was episode 58 and that was published back on November 26th, 2021. Really encourage you to go back and listen to that episode. Ed’s been very busy but he’s found some time to come in and talk to us. So we’re going to recap Ed’s Cyber Path, how did he do what he did, which we discussed in detail on episode 58. Then we’re going to talk about how he successfully negotiated his pay raise. So Ed, so glad you’re here. Thank you for being our guest again and for sharing more of your story with us.

Ed Skipka:
Of course, it’s an honor to be here again and I forgot to thank you in the first episode and I been kicking myself ever since. I just launched cold right into my story and I’m not going to miss that opportunity now. I appreciate you having me back on. It’s an honor and anything to help anybody else out there. I’m here for that.

Kip Boyle:
I love your generous spirit. Thank you so much. I’m sure nobody listening to your previous episode was probably thinking, “Man, I really wish I had taken a couple of minutes and thanked Kip.” They probably loved that you just jumped right into it. But listen, it’s not a problem and that’s just your generous spirit. But really there’s such a overall spirit of generosity I think in the cybersecurity career field. It’s not a very big field and I keep encountering the same people again and again. What’s really interesting is sometimes when I encounter somebody, we are just coworkers on a team and then the next time I encounter them, they’re my customer because we’ve changed jobs and then the tables turn and then I’m their customer and then they show up to interview for a job and I’m on the interview board. It just goes like that.

So it really pays to be generous and treat people right and I just really like the way you do that Ed. Thank you.

Ed Skipka:
Thank you.

Kip Boyle:
So let’s get to it. Now first of all, let’s do a quick recap. So anybody who hasn’t listened to episode 58, but I think you all know, go listen to episode 58. That’s what I want you to do. But let’s do a quick recap. So you’ve got a bachelor’s degree but it’s in education and music, right?

Ed Skipka:
Yes. Since our last interview I’ve gotten my second bachelor’s, but I won’t jump over the cart here just yet. But yeah, my beginnings were as a musician, have a dual bachelor’s in professional music and music education, Berkeley College of Music. Totally into music, didn’t have a technology background. Berkeley used a lot of technology in the school and to bring it to education. But I was not a comp sci or an engineering, electrical engineer. None of that type of background to how I got in.

Kip Boyle:
This is one of the reasons why I think you are such an encouraging person because we talk to a lot of people who come to us and say, “Oh, I didn’t study technology as an undergraduate. Do I have any chance of getting into cybersecurity?” We’re like, “Heck yeah.” They get surprised. They’re like, “Really?” We’re like, “Yeah, it can happen to you.” I think you are a wonderful poster child for the fact that Jason and Kip are not lying when we say that.

Ed Skipka:
Don’t pin all your hopes on me, but I can be at least that for you.

Kip Boyle:
Yeah, that’s great. Then at some point before you switched into cyber, tell us about what kind of work history you had.

Ed Skipka:
I was just doing odd jobs out of Berkeley and just teaching on the side a little bit. I was at a bike shop. I started a little bit before completing Berkeley, Great bike shop, Landry’s Bicycles in Boston if you ever around there, great people. I sold bikes and I took it upon myself to kind of be the backend associate analyst person for the work orders. But I like selling bikes, I like improving people’s lives. But I saw these little things. So we had work orders and orders and repairs and all this logistics stuff that was in an Oracle database and I found ways to kind of pump up the efficiency but it was really good.

I bought lots of bike equipment because it was half off and all the people around me were very passionate about being healthy but not in a toxic way. They just wanted to improve everybody’s lives and they were very passionate about what they did and it was a great environment. Before that I was working in some restaurants and it’s a mixed bag. I liked a lot of the people but you can see that it’s totally different vibe. I was working late nights and my health was not the focus at that a point. So really moving over to the bike shop was a step up for me from that transition from college.

Kip Boyle:
This is the other thing that I really like about your story is not only do you not have a technology bachelor’s degree, but the way you got into this is you figured out how to make technology kind of like an additional duty for yourself so to speak. You took it upon yourself to start messing around that Oracle database and to start learning technology on the job. So many people have jobs today that strictly speaking are not technology jobs or maybe they are in a technology job but they don’t think that they can do any cybersecurity and that’s just not true. There’s so many opportunities you just have to look around and find them and then get yourself into it. I think that’s been a key to your success. We certainly try to encourage people to do that. Okay, now how did you get your first tech job? Tell us about that.

Ed Skipka:
Sure. So there was a number of years, just odd jobs holding down the fort. Unemployment here and there, which can be discouraging after a while. But talking with a friend, they were actually going to be leaving Oahu at the time, but before that he was actually a regional manager so it pays to know somebody.

But, he got me an interview and I got in the room and I made sure to have a clear folder that had my SEC plus Professor Messer and Jason Dion notes on the back so they knew that I was working on my cert at the time. So when I walked in the room they’re like, “Oh yeah, he is working on it. He doesn’t have the experience but he’s working on the cert we need him to get.” They saw that and I went to school or I had learned some things in the past and that really informed that I’m hungry to learn. I really wanted to be there. It wasn’t just a job. I was looking for almost a new purpose honestly in life. I was attacking it with vigor and curiosity that I wanted to be there. They said, “Okay, you just find a subcontractor to us. We’ll give you a shot. You have 90 days probationary period.”

My buddy actually had me talk to another subcontractor. They looked through my resume, they’re like, “Well you’ve done some logistics things, you have a bachelors and it’s in a different thing, but we could tell that you’ve learned a lot of stuff in the past, but you do need to get the SEC plus. Once you do that we can start your clearance process because this is a government job,” which is another hurdle. I found somebody that was able to sponsor that first clearance if I could. That’s pretty big. But the state of cyber right now, I think people put more hurdles in front of themselves because of that clearance than they need to, especially at a lower level of clearance. If you have some certification or background that you can show, people might be able to take a chance on that lower level of clearance and you can build your way, build your jobs up.

But they gave me a chance and I got into that tier two, which in this would mean a step above help desk. So, we were field service engineers or technicians that would go out on site to do the IT work.

Kip Boyle:
Right. Well yeah. Now again, more great things about your story about how you were able to demonstrate some of the things that I call skills that can’t be trained. Curiosity. I can’t train somebody to be curious. You’re either curious or you’re not. I don’t know how to create curiosity in a person who doesn’t already have it. So I love that. I love the fact that you’ve managed to find an opportunity where people were willing to take a chance on you, particularly the security clearance. But we go into all of this in great detail in episode 58, so I don’t want to unpack everything here.

But anyway, so you got that IT job and you were in the field service and then I think you went for a watch officer, so you had a completely different experience there where you were working at night and it was boring a lot, right? So I would say you put in your dues. I mean you were willing to work jobs that maybe most people would not be willing to work because they wouldn’t think that, maybe that work was beneath them. I don’t know. But it’s certainly not the best schedule for somebody. But I think sometimes you have to make these kinds of trade offs. Is that what you were thinking?

Ed Skipka:
Right. Yeah. I mean when I got into IT, I didn’t necessarily say I want to go into cyber security, I’m going to make some money, I’m going to cert up. It was a job and then it became a passion and then I really liked cyber. So at that almost two year mark, I was like, “I want to get to a place that has more cyber.” My contract said, ‘Hey, if we get you over here, more stuff going on over there. But yeah, it is going to be night shift. You’re going to be working 9:00 PM to 7:00 AM and you’re just going to have to deal with that for a while. You’re going to pay your dues and you’re going to get an opportunity that comes in front of you possibly.”

Yeah, I use that time because it was boring because no one’s there. We’re monitoring east coast, west coast, all of the Pacific AOR, but a lot of people still aren’t up. So you’re watching TV. We had three TVs in there, we had to keep one as our operations, but the rest we could do whatever we want with. I took that time to fill in some gaps of knowledge.

But yeah, it took a little over two years to get to where I am now. My third job, you always talk about the two step. I had a three step, it took a little over two years but it seemed to go by fast and you want to use that time wisely. So when you land that first job, you’re useful on day one. You don’t want to get the job before you’re ready because then you can really mess up your reputation. You get the job and you’re not very useful and they’re like, “Oh well we’re not going to give that guy another chance. He really messed us up.”

Kip Boyle:
Yeah, 90 day probation. How about 30 day probation?

Ed Skipka:
How about this week.

Kip Boyle:
Yeah, a week of probation. So fast forward you got a really great cybersecurity job as a vulnerability management analyst. Now, I noticed there’s some acronyms sort of after your job title like HBSS/ESS. What’s that?

Ed Skipka:
So HBSS, host based security system, ESS is a branch off of that. It used to be under McAfee, a McAfee product for host based security. So there’s a little agent that’s Tattle Tale that’s on all these endpoint servers, whatever. It monitors. It has data loss prevention on it, it has policies, it has firewalls on a host basis. So I wear two hats, but I am more on the scanning, vulnerability scanning, and enumerating and all informing assist admins to how to patch and what to do. But I also do that host base security for McAfee Trellix. That’s a big thing within the DOD is that’s kind of their solution for host base. There’s carbon black and all these other offerings, but that’s what the DOD bought and that’s my other hat that I wear.

Kip Boyle:
Got it. Okay. Now and again we’re just kind of recapping because we really want to get to the subject which is how did you get this pay raise? But since you had your interview with us in the episode 58, you told me you did as you finished your bachelor’s degree in cybersecurity and information assurance. You’ve put three more certifications in your pocket and you actually moved up to take more responsibility, which is what you were just talking about there. Then, at about the eight month point you got to pay raise and you won a company award and that’s not even the pay raise that we’re here to talk about. Tell us a little bit about how you got the pay raise and the award.

Ed Skipka:
Also, I mean you have to find your mentors and your advocates. I understand that for some workplaces you are going to be paying your dues. People are always worried about themselves. They might not be very apt to build you up. I always find that it’s incredible what you can achieve if you don’t care who gets the credit.

A lot of times it’s not the case, but there is going to be somebody, their supervisor, a fellow person that’s been there longer. So I found my advocates and that happened to be the person that really got me the job or at least got me set in for my interview, who was a former customer, was the project manager for the contract that I was going to be working on. So he’s like, “We’ve had a lot of people come through. I see you’re ambitious. You’re doing all these things and I want to build that.” He has a PMP. So very project minded and building people up in progression. So I kept documentation and metrics of all the things I was doing, this many accounts, our compliance went from this percentage to this percentage and I was able to show exactly what I did and how it helped. You don’t necessarily want to overdo that.

“Wow, I am so helpful.” It’s like, “Yeah, that’s why we gave you the job to do the thing.” But you can show this is my job that I’m doing the job. But here are the things that I’m also doing above that. That would necessitate almost a raise because it’s like, “Wow, we want to keep you around. You’re becoming extremely valuable and you’re solving all these problems above what your just day to day tasks are.” You want to make it to the point where they almost feel compelled because they want to keep you around. So, that’s how I started the process.

Kip Boyle:
Yeah, retention, right? Hiring managers, the supervisors, if you’re doing a great job and you are checking all the boxes, you’re getting things done, customers are happy. Well the supervisors want you to stay and so giving you a pay raise is a form of doing that, of retaining you, of letting you know that we value you and we want you to hang around. Now you got a 25% pay raise, which is amazing. You talked a little bit about how you did that. What else? So think about the people who are listening to this episode and they’re like, “Man, how could I do that?”

 If I remember correctly from planning this episode, one of the things that happened was you interviewed for another job. That was part of the story about how you got your pay raise, right?

Ed Skipka:
Right. I initially engaged with my project manager and was like, “At six months we’re going to put this letter in and we’re going to see if we can get you nominated for that quarterly award,” because they do it quarterly, which is weird to be nominated for a quarterly award once you’ve been there for one quarter, but.

Kip Boyle:
Good for you.

Ed Skipka:
So that’s where we were going for and then we just built on that and being in the DOD, there’s the 8570, which is the certifications that kind of tell you where you are in your career. So for me, it was a little bit easier to show my progression. My clearance upgrade also got adjudicated so I was more valuable cause I wasn’t waiting for that higher clearance. So that was valuable. But getting the cloud security professional from ISC Squared bumped me into another tier of a IA technician three where I was a two before. So, that was within the DOD. I was able to show I’m no longer, I did these job duties but also within the industry I’m growing and growing. So I engaged with our program manager who has been very receptive, but they are program manager. They look at numbers and they look at people and they’re like, at first they’re going to say, “Well why would I pay you more? You’re doing a great job. Well if you want to go somewhere else then that’s really what it’s going to take.”

So we had a nice conversation, she was very understanding and she was like, “It would really help if you had an offer.” I’m like, “Okay.” I had been engaging with a recruiter because you find once you get four, six, eight months into a cyber position, you have a couple certs, that initial hurdle of getting another job falls away. Recruiters are contacting you on LinkedIn and I increase my engagement on LinkedIn as well. But they start coming after you. A lot of times it’s jobs that are not jobs you want or the pay you want, but they’re at least reaching out to you. So a recruiter had reached out to me for basically the same job I was doing before, the tier two job, the first job. I said, “You know what? I already had that job. I feel I’ve exceeded that in this many ways. This is where I would like to go.”

I went on to their job board to their website and I said, “You know what? There’s a security engineer senior position. That sounds really attractive to me. I’d really like that.” So we set up a call, we talked about it and she’s like, “Yeah, it looks like you’re lined up. Your years of experience isn’t quite where they want it. They wanted seven to ten years, like every other position. But I’ll get you with the account manager that oversees that and then we can see what, if you get through him then we can possibly set up an interview.”

Kip Boyle:
I love that you were not put off by that, by the way that I’m sure you saw that, right? The seven to ten years. But you just kept going and I want to compliment you for that because a lot of people would be like, “Oh, I’m not even going to try.”

Ed Skipka:
Yeah. We’ll find out later how it turned out. If it’s like a director level, I know I can’t even do that job whether I wanted to or not. I don’t have the acumen and the years and years of experience. I would fail at that job. I don’t want to be a CEO or a CTL right now. I think I would be at this point, not ready to, I would be a disservice to that job. But engineering jobs and they’re like, “These are the skills you need. Here are the certs you need and here’s where we’re going with the position.” I’m like, “That actually sounds like exactly what I’m want to do and expand into. I have a lot of those qualifications, at least 60, 70% of the qualifications perfect. So why not? Get me in front of a person, see if I can talk to him.” Then that’s how I got to the account manager and he liked my resume. Again, it kind of talked about the years of experience, but he’s like, “Well, we’ll set up an interview.”

Kip Boyle:
So what were you thinking at this point? Because origin, the reason why you went ahead and responded to a recruiter’s outreach to you is because you were trying to get this pay raise. The advice that you had gotten in that process was, “It would be great if you had an outside offer, right?”

Ed Skipka:
Oh 100%. I really wanted to stay where I was because I liked the team, at least for a little bit. This is a really good developmental area where I could learn a lot. The schedule is more flexible. People are understanding, you’re left to your work because it’s kind of a SME level position where you do your work, you’re expected to do your work and then people don’t micromanage you.

So, that’s tough to find. But I was coming up on that six to eight months and I’m like, “Well the rest of the industry is going to pay me this and I really like this. But at the same time, if I could get paid 25% more, that would really, I’ve already gotten about a 18% bump from my last job. This would really put me in a bracket and a spot that I could be really comfortable and really make some moves and pay down some student debt from that first degree. This would be great.” So I wanted to stay, I engaged with it because.

Kip Boyle:
Now at this point, you’re doing it because you want get that increased compensation, which is completely understandable. But at this point were you starting to think, “Oh wow, here’s a senior job that I might be able to get because I’m getting these signals from the organization that, ‘Okay, you’re not quite meeting all the requirements, but we do what we see. So let’s keep talking, let’s keep talking.'” I’m wondering at this point were you thinking, “Well maybe I am going to leave this employer that I’m with now because we’ll see what happens.” But I got to think that you were at least starting to think about the possibility that you weren’t now just trying to get an offer to increase comp. You might actually get a different job from this.

Ed Skipka:
We did go on to two interviews after those first screening calls. The one was with the security ops manager. I did well with that. I really liked the guy that would be my overhead. Not my direct report, but my boss’s boss or boss’s boss’s boss. I was like, this is a really cool guy. This seems like a cool mission. Then I got in with the engineers and a net ops lead and I was like, “These people seem like they would be cool to work with. It’s work from home and you go in every Friday, maybe two times a month and everybody’s just trying to bust out certs. They’re going to Sand’s Institute, they’ll pay for it once a year maybe.” I was like, “Yeah, this is actually sounding pretty good.”

But again, that was a real confidence booster that I was engaging with it. This was one of the first opportunities that I didn’t have an inside person. I didn’t have a referral. This was someone that reached out to give me my old job two jobs ago. Somehow I’m talking about a senior position where a year and a half ago I wouldn’t be looking at senior security engineer positions is like that’s, “Well maybe five years from now.” This is not even in the ballpark of me even being able to do that job. I engage with this opportunity knowing that I could be at least 60 to 70% of what this job needed. That happened very quickly within the last year, year and a half. That was cool.

Kip Boyle:
Ed, I’m seeing that too. Just so you know, and for everybody who’s listening, there is a lot of opportunity to have career progression sooner than you expected because there’s a lot of demand for people with curiosity and integrity and who show up with humility and they want to learn. So, even if you don’t quite meet all the requirements, there’s just this sort of vacuum that’s happening and it’s pulling people up faster than they might otherwise be able to do. So I’m really glad you mentioned that. On my team, I just experienced that in a very real way because I hired somebody six months ago and I didn’t expect him to stay for a long, long time. But during the hiring process, we got to talking and the impression I came away with was, “Well maybe he’ll stay on the team for two or three years.”

But boom, right about the six month point, he came to me and he said, “I just got offered my dream job, Vice President of Information Security at this credit union.” I was like, “What can I do? I’m so happy for you. I’m a little disappointed for me, but I’m so happy for you. Absolutely. With my blessing, you should go and do that and whatever we can do to help you be successful in your new job, just let us know.” But yeah, that’s one of the cool things about being in cybersecurity right now.

Okay. Sorry, that was a big divergent there. So let’s get back to your story. Now you’re starting to have conversations about this new senior position. Then what happened?

Ed Skipka:
Well, they were kind of stalwarting me a little bit because they’re a business. It’s very tough because this company that I work for it’s a family. It’s an ohana here. It’s local and folks getting together and we’ve been out to eat. I’ve been out to eat with the program manager and the VP above her. I got along with them, they’re great people. Now I’m kind of met with this business front where it’s like, “Come on. You know me. You know I’m good for it.” But they had to go through two or three VPs, because that’s a significant raise. I acknowledge that it’s tough to get like, “Hey, I want 25% more that.” That’s a lot.

Kip Boyle:
That’s a big number.

Ed Skipka:
Yeah, that’s a big number. So I had to go through a lot of folks. I was just more and more I was like, “I kind of like this other job. It would be nice to have the flexibility of being home.” I’m a person that actually would prefer a hybrid. I don’t want full remote or full there. But I was like, it would be nice three, four days of the week to be home to take care of some stuff, but I also take care of your work and these people are really cool and I see this could really launch me off on another branch of the tree. This could be a good opportunity for me. So it went from 90% wanting to stay, even if they met half of what I was asking for to, “Well there are other people that value me at this number.” Things are always worth what someone’s willing to pay for them. You have to steal yourself away slightly and not take it personally and just look at it.

This is your value and you can build that value and you can seek out that value and there’s nothing more valuable than someone else saying this is worth something. You put a number on it. I went to them, I said, “This is the posting, this is what they’re looking to pay this position. This is what I’m asking, which is actually less than that and I’m actually advanced in the stages.” It took about two and a half weeks for them to come back to me with that final like, “Hey, it’s going to start.” They actually gave me that in the middle of May and they started that raise in June. So they actually started at the next pay period, which was, that’s awesome too. But it took two and a half weeks and every a week would go by, I would send them an email.

Then that second week I was a little bit more aggressive. I said, “Hey, I went through two screenings two interviews. I believe they went extremely well. Again, this is what they’re looking to pay this position. I’m actually asking for less. I would love to stay, I would love to build this team, I would love to keep building with this team.” They’re like, “Okay, thank you for being so frank and upfront about this.” I don’t think you need to be aggressive and mean, but it’s all about leverage and not taking it personally in that point. You just have to say, “I am worth this. I am worth this number at least and if not more, I could probably go find somebody else that’s going to pay me more. This is what I’m getting now. This is what I’m asking for and I believe I deserve it.” I’m not entitled to it, but I deserve it.

Kip Boyle:
I think you also have to be ready to leave if they rebuke you. If you get to that point where you’re having that conversation, in order to be credible, you already have to believe in your heart that if they’re not going to give you the increase that you’re going to leave, right? Because if they don’t give you the increase and you stay, then one of the messages they’ll get from that is, “Oh, he was never really that serious and so we don’t ever have to worry about this again. He’ll never come back and try to do this again.” You don’t want that, right. That’s not a favorable position for you to be in.

So let me recap something here. So you’re at your current employer. You’re asking for an increase in your compensation. They say, “It’d help if you had an outside offer.” So you go off and you get an outside offer and then you bring it back and you go through this process and ultimately you win and you do get increased pay in your current job. But I want to explore something else. What did you do with that outside offer? What happened there? Because did they actually offer you the job?

Ed Skipka:
So here’s the kicker. Maybe you can hear my cat in the background.

Kip Boyle:
Nope.

Ed Skipka:
Good. Very, very good. The kicker was I didn’t get my offer, my official offer letter before getting the raise. I said, “This is the range, this is how far I’m in the process and I am serious about leaving,” which I was. You do have to have that in your heart that in every negotiation, you have a number and you have to have some dignity about it. Again, not personal, not taking it personally. This is what I’m worth and I thank you and no thank you type of thing. So, that was my number. I was sticking to it. They said, “Can you lower the number? Can we have this as a series of raises up to that number?” I said, “No, this is actually what I’m worth within the industry.” They gave me what I asked for exactly, which was great.

Then maybe three or four days later, I got a call from the manager, the account manager said, “We’d like to offer you that job.” Here’s the thing was he said that was a level three senior or level four engineer position with this company. He said, “We want seven years of experience. You have three, four. We’re going to give you a level three, which is going to be.” At that time the top end of it was going to be about a 15% raise. So I was like, “I really like your mission and I have already been offered 25%. Is that a possibility?” They’re like, “No, this is really what the customer came back with.” I was like, “It’s bittersweet. It was disappointing.”

But that’s what they came back with. I said, “I thank you very much for the opportunity to interview with you. I really like the company and the people. The team, it’s great. But I have been offered more. Not an insignificant amount, 10% over what you’re offering and I’m going to have to go with that because I really already liked the job I had.” If I just absolutely did not and I wanted to jump ship, then I probably would’ve taken that 15%. But, they came back three days later with the offer and said, “We’re going to give you a mid senior and rather than a senior position, is that okay with you?” I actually had to turn it down because it was less than I had originally negotiated with my current company.

Kip Boyle:
That’s fabulous. Okay. So what I’m hearing you say is you were in the perfect position, you had two employers, your current employer and then this other employer. They’re both seeing you as irresistible. They both want you on their team and you are the one who gets to choose which one you’re going to take. On your own terms, and Ed, this is what I want for everybody that I work with who are coming to me and saying, “Kip, how do I get into cyber security? How do I get promoted? How do I get a pay raise?” This idea that you get to choose from multiple competing offers, both of which are better than the one you have right now. Congratulations. What a wonderful place to be.

Ed Skipka:
Thank you. What works for me won’t necessarily work for everybody else, but there are lots of bedrock foundations that you can build in yourself, building it up. I’d say not including my mileage, and over time of that first job, which I had already said in that other episode, was my secondary income. If you just take my base rate of pay, I’ve just about doubled my pay in about two and a half years.

Kip Boyle:
That’s amazing.

Ed Skipka:
Which the pay when I first started it was not bad at all. So it’s not like I was going from $5 to $10 an hour or something like that. But, through this journey I’ve seen people that are happy or complacent. You have to make that decision for yourself. If you’re happy where you are and you work for a school system, you’re going to get paid less, more than likely. You have to weigh these multiple things, Work life balance, benefits, package, flexibility, the team you’re working on. Because if you just go to another job because you’re going to pay you more and you’re miserable, leave in three to four months and that is really bad. It doesn’t look as bad in the DOD contracting world.

People hop four to six months all over, doesn’t necessarily matter that much, but if you’re in the private sector and you stay there four months and you have a bad experience, they didn’t like you or you didn’t succeed, then that’s just going to shoot you in the foot. So, the other things I was looking at for this job was, “Okay, they offer me 10% less, but again, this security engineer, they really wanted a threat hunter and that’s something I’m really interested in. I want to get more into that.” In vulnerability management, you’re kind of doing things after the fact to kind of drive compliance. You’re doing security operations rather than forensics and catching the indicator of compromise. So that was really attractive to me that I could be a threat hunter for all these different folks. Other thing was that it was work from home hybrid. For some people that have to pay for daycare or don’t prefer to commute. I commute a total of an hour and a half a day, hour and 40 minutes and some days that really grates on me.

So you take your pay rate at least and the time that you’re driving and that’s how much time you’re losing every day. You have to wake up earlier. So that you have to take all these things into consideration. My first job up to this job, I’m getting paid more, but also I pay way less for my medical, which is another thing. If they don’t pay any of your medical or they have a very, you can end up paying $500, $600 per person for your medical. If you take more money, but now you’re paying significantly more for your medical, you have to take all these little pieces into account and how it’s going to benefit you. Don’t just look at a number. It’s a total package and it’s your life. I mean work life balance. It’s kind of funny to say that, but work is also your life.

You have to take you that into account. If you’re going to be extremely miserable, you better be getting paid a lot. You can totally enjoy your time off.

Kip Boyle:
Your misery costs. Well what a confidence booster that must have been for you to have those multiple competing offers and to make your choice and just downstream of that. Right. Wow, that was really cool. Had you ever been in that situation before, Ed?

Ed Skipka:
No, not at all. I mean, I’ve always tried to get at least one referral or endear myself. When I got the bike shop job, I was a customer there and I talked to the people and they liked me and I was friends with one of the people that worked there. So I got that job doing that. When I was doing my education degree, I got my practicum, the student teaching by going out and shadowing this teacher.

They didn’t usually take people on, but they liked me and they gave me a chance there. So throughout my life I’ve been helped greatly by other people by talking to them and using those soft skills. I’ve never been in a position where someone’s reached out to me and just cold. I’m like, “Well no, I would like this position actually.” Then finding a way to interview through that. It was really a validation of the skills I’ve built over the last year, year and a half. The confidence that I’ve gained by just being around great people that have helped me and learning more. Never stop learning where I felt confident in that position where I wasn’t just doing a Hail Mary applying to. I didn’t even apply to 300, 500 positions. This person reached out to me. That was the only thing I applied to.

I had two others that reached out that were. It just was not going anywhere. So I didn’t apply for them. So it was literally the only other job that I applied for. But just being able to get through that first and second hurdle to talk to a person. Yeah, I mean that’s always the hurdle.

Kip Boyle:
You’re right. That’s another thing that I love about your story and why I’m so glad we can share it with the audience is you never had to worry about getting through the applicant tracking system. You never had to worry about getting noticed about getting us a hiring manager to notice you because they came to you. So you were able to skip all of that tedium of having to customize your resume to get those keywords correct. To try to figure out like, “Oh, who’s the hiring manager and how can I get a message to them?”

I mean, all of that shuffle, it just didn’t even happen for you. Not only that, but you’re a more experienced interviewer now than you were before, right? So.

Ed Skipka:
Yeah, no, the interviews. The first one was a behavior interview, but even that was great just to hear, again because it’s been a while. I got that first job a little over three years ago or whatever, and that again, I had somebody there. So the interview was, “Hey, you’re going to get your SEC plus, right? You’re going to do this.” So I wasn’t getting grilled. Those [inaudible] interview, and it was all coming upon me to get that SEC plus. Then the next job was just to roll over on the same contract with my current contract supervisor. So it had been a while since I had been in front of someone that was asking me probing questions and the second interview was a tech interview and it was probably an hour and 15 minutes.

Kip Boyle:
Wow.

Ed Skipka:
20 minutes and asked 20 to 30, maybe even more questions. Maybe even more. “What’s the diamond model? What does that mean to you? What is threat hunting? Where would you find indicators of compromise within a file system? What is risk? What is vulnerability? All these, some of them were, that’s a lower level question. But you need to know it cold. “What would it mean that somebody is attacking from Russia?” You have to back out of that question and say, “Okay, geopolitical things going on.” You have to be creative about it. “How would you direct and deliver threat hunting program?” So I have these banks of questions now, 30, 40, 50 of them that I did write them down. I have a decent memory. I wrote them all down and I knew about 85% of them, which is always a good place to be in.

I did prep for that interview for about a week. I looked up threat hunter questions, thought questions. But they asked some questions I hadn’t even thought of. That will only help me in the.

Kip Boyle:
That’s right.

Ed Skipka:
Keep your finger on the pulse of what are people asking of you for these types of jobs.

Kip Boyle:
Sooner or later you’re going to go for a threat hunting job probably. Now you’ve got all this interviewing experience and extra knowledge. So I mean, it was really worth the effort for you to do this in so many different ways. Ed, I’m so happy for you and I’m grateful again that you came to share your story with everybody. Thank you so much for being here. What I want to do now is wrap up our time together. So listen everybody. Every episode that we publish, we publish show notes and you can get those show notes really easily.

You just put the episode number after our URL. You put yourcyberpath.com, forward slash, and the episode number. You put that in your favorite web browser. This is episode 81. So you just put 81 in your web browser there. Then you can go check out the show notes and you can actually also get a transcript of everything we’ve talked about. You can also go to yourcyberpath.com to sign up for my mentor notes. Okay, well why should you do that? I mean, you should be asking yourself that question.

Well, I’ve designed mentor notes to teach you how to get into the cybersecurity field and then succeed from all kinds of different angles. I write about all kinds of different things. Sometimes it’s, “Hey, there’s an apprenticeship program that’s open, go check it out.” Sometimes it’s just, “Hey, here’s a skill or here’s a trap that you might fall into at some point. You want to see this and not fall into it.” But each mentor note is practical and short. It’s only about 500 words. Very easy for you to read. It’s easy to unsubscribe in case you don’t like it. So I’d like you to give it a try. Go to yourcyberpath.com, sign up for it, see what you think. In the meantime, Ed, thank you so much for being here. Hope you all have a great week and we’ll see you next time on Your Cyber Path.

Headshot of Kip BoyleYOUR HOST:

    Kip Boyle
      Cyber Risk Opportunities

Kip Boyle serves as virtual chief information security officer for many customers, including a professional sports team and fast-growing FinTech and AdTech companies. Over the years, Kip has built teams by interviewing hundreds of cybersecurity professionals. And now, he’s sharing his insider’s perspective with you!

Headshot of Jason DionYOUR CO-HOST:

    Jason Dion
      Dion Training Solutions

Jason Dion is the lead instructor at Dion Training Solutions. Jason has been the Director of a Network and Security Operations Center and an Information Systems Officer for large organizations around the globe. He is an experienced hiring manager in the government and defense sectors.

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