We often talk about the contradiction of seemingly entry-level security jobs requiring years of experience. But maybe that’s because entry-level jobs don’t actually exist.
Check out this post for the discussion that is the basis of our conversation on this week’s episode co-hosted by me, David Spark (@dspark), the producer of CISO Series, and Geoff Belknap (@geoffbelknap), CISO, LinkedIn. Joining us this week is our guest Jay Wilson, CISO, Insurity.
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[David Spark] We often talk about the contradiction of seemingly entry-level security jobs requiring years of experience, but maybe that’s because entry-level jobs in security don’t actually exist.
[Voiceover] You’re listening to Defense in Depth.
[David Spark] Welcome to Defense in Depth. My name is David Spark, I am the producer of the CISO Series and joining me for this very episode, you all love him, I know you do. If you don’t love him, we have to have a talk. It’s Geoff Belknap, the CISO of LinkedIn.
[Geoff Belknap] I feel like sometimes you set an incredibly high bar here.
[David Spark] In fact, I think it’s a low bar. I think most people should be infatuated with you. I’m going down to loving you.
[Geoff Belknap] I appreciate your optimism and I appreciate all of our listeners. Thanks for tuning in, it’s going to be a great show.
[David Spark] We guarantee that.
[Geoff Belknap] David guarantees it. I make no such promises.
[David Spark] I guarantee it or your money back.
[Geoff Belknap] David will return your money. Again, I make no such promises.
[David Spark] Our sponsor for today’s episode is good friend of the CISO Series SlashNext. Greatly appreciate their support. Complete generative AI security for email, mobile, and browser. Pretty much anywhere messaging comes into your system, they have a protection layer there for you, can stop it, and is definitely taking advantage of generative AI to deal with the more creative social engineering attacks that come through your gateways.
More about that later in the show.
So, Geoff, I want to talk about the cybersecurity skills shortage, which we have brought up a few times on this show before. It’s kind of accepted wisdom at this point. I mean, we’ve seen reports after reports, and now the numbers are like mind-numbing because it started at a million, now it’s 2 million, now it’s half the world population, I think.
So, if the industry has millions, I don’t know, billions of jobs to fill, why does it seem like there are still no entry-level jobs? In a recent LinkedIn post, vCISO Olivia Rose broke down why all the certifications in the world won’t make it easier for someone with no cybersecurity experience to land an entry-level job.
Is this just a matter of a tightening economy? And how do job candidates get creative with their experience to get a foot in the door?
[Geoff Belknap] I think there’s a couple things going on here. Number one, as we’re recording this right now, there is a bit of a contraction in the job market, so that complicates matters. But I think if we abstract this to cybersecurity or information security in general, it is very difficult to get your foot in the door, which is why so many people start with certifications and various trainings.
Honestly, I think a lot of that is our own fault. It’s people in roles like mine that are working with HR teams or recruiting teams that are setting a bar that is unreasonably high because we only have so many roles open. I wish we have 3 billion or a billion roles open in cybersecurity. We just don’t.
And because we don’t, we try to set the bar really, really high hoping that we’re going to get a perfect person and we forget that this thing, cybersecurity, is going to go on for a while. We got to build kind of an ecosystem that trains people, and I think today we’re going to have that conversation to figure out how do we make this better.
[David Spark] Joining us for this conversation is a gentleman I had on stage in Denver, Colorado. He was on the CISO Series Podcast, we did a live version of it. He was awesome on stage. I said, “You know what? Are you good talking into a microphone when you’re not on stage?” and he, like Elvis, he has to do a lot of his microphone performance in front of an audience, but he’s actually going to pull it off for us right now.
Without a live audience, but I’m expecting a lot of screams from the listening audience as they’re in their car or jogging, wherever they are. You can pull this off, yes, Jay?
[Jay Wilson] Yes. Although I’m having a hard time not laughing right now into the microphone.
[Geoff Belknap] Sometimes, David, these buildups are the entire reason I listen to the show. It’s just for these.
[David Spark] I appreciate that. None of these embellishments are incorrect. These are on the money, I want you to know.
[Geoff Belknap] I endorse them.
[Jay Wilson] At least my bar was lower than Geoff’s, which I am very happy about it.
[Geoff Belknap] Very achievable.
[David Spark] By the way, let me introduce…
[Geoff Belknap] Yeah. Who is this guy?
[David Spark] This guy is the CISO of Insurity, it’s Jay Wilson. Jay, thank you so much for joining us.
[Jay Wilson] Thank you. Nice to be here.
Sometimes it’s really not that difficult.
[David Spark] Seth J. Kirschner of DoubleVerify said, “I disagree.” Disagreeing about the job problem. “There are dozens of entry-level jobs in the industry, but you have to know where to look.” Seth mentioned vendors looking for account execs and biz dev reps. And consultancies and MSSPs looking for interns.
Analyst positions now have training programs. James O. Holley of 3M said, “I also disagree. Many companies have intern programs focused on early identification of cyber talent. Both as Global CISO at Caterpillar and a Managing Director at EY, I had college interns every year get experience in my cyber organization, and we hired more than one of them every year directly from college into an entry-level cyber role.” And lastly, Keith Price of Envision Pharma Group said, “There is more interest in hiring entry-level folks and developing them outside the USA, whereas in the USA and due to 10,000s of mass layoffs last year, there is more competition for jobs.” So, Geoff, we’re beginning with people arguing the premise that there’s no entry-level jobs.
What do you think?
[Geoff Belknap] I think there are not nearly enough entry-level jobs is basically threading the needle on that conversation.
[David Spark] Yeah, I would agree on that. I think they exist but definitely not enough.
[Geoff Belknap] 100%. Like I was saying earlier, right now there’s definitely very few jobs in general, but that’s cyclical. I think the longer-term problem on this is we… I think there’s a great example here from James that talked about like, “I take an intern every year.” Like, great. It can’t be one, right?
There can’t be 1% of all hiring at cybersecurity can’t be the entry-level role. And frankly, if you’re coming out of college, you’re getting more than just an entry-level experience, right? So, I think the solution here is for people like me, and especially for organizations like me, to make sure that we are building pipelines that, almost like the military or like the medical profession, that start in a structured way of you have a base set of knowledge and you will build it over the years into being a fully high-performant InfoSec engineer in one discipline or another.
And we’re getting there, but we’re still not quite into that pattern yet.
[David Spark] It isn’t quite formalized yet. Jay, what do you think of the premise of, “Hey, we do have entry-level jobs”?
[Jay Wilson] I think that entry-level jobs exist, like Geoff said too. But it’s one of those things that I think we all are challenged with as CISOs because the reality is we have a huge mandate, we have usually confined budgets, and the first thing that is on my list is not to hire an intern with that confined budget and large problem space to solve.
So, I don’t look at it as a pipeline problem I need to solve, but I definitely agree with what Geoff is saying. We need those pipelines, they need to exist, it’s just not my focus so I don’t have that right now.
[David Spark] Now, do you have the breadth and the availability to create some kind of pipeline in your organization or it’s not even set up that way? Because some organizations just simply aren’t set up to be able to do that, and some larger ones, and I’m thinking like we had a reference to EY, I definitely know they have it set up like that.
[Jay Wilson] Yeah. I think we have limited. Insurity absolutely hires interns from time to time, but I think that the question isn’t about interns at a broad stage from a pipelining perspective, it’s about cybersecurity interns. And when you step back into the difference between those two, what are we talking about?
When I hire an intern for two months in between college semesters, what is it that they’re going to do and learn, and I am spending as much time teaching them as I am getting something from them, and all those kinds of questions kind of emerge in my head. So, I actually had someone recently approach me about, “Would you take an intern on?” I said, “Well, how long would they be here?” Because the answer’s, “Yes, I’d take an intern.” But I don’t want someone to show up for two weeks or three weeks or some period of time like that because by the time they’ve even understood our 25 different products, then they’re out the door.
[Geoff Belknap] I do think there’s a little bit of responsibility larger organizations like mine have here. It’s like I have hundreds of people in our web security organization. I absolutely have the room to build a pipeline or developmental program. And certainly at LinkedIn, we do that exactly. But I think more people need to be thinking about the skills they need to develop people into those fully-performant engineers so that people like Jay or somebody who, I don’t know, is doing security for a dental office or something don’t need to carry that full burden.
I didn’t think of these options.
[David Spark] Timothy Pham of Free Geek said, “Pretend you’re a hacker trying to get into this system called First Cybersecurity Job.” By the way, I love this setup here. “The way everyone else has been trying to get has been patched. You got to think like a hacker and get creative. You might need to enter the network as another user and do some lateral movement or privilege escalation.” Great, great theory of approach.
And Edward Mattison of Practical Security & Property said, “The best path for these cyber newbies is to take entry-level jobs in IT. Focus on security tasks when they get the opportunity, get a certification or two, then move over to cyber jobs that need some prior experience. There is always a path, sometimes it is longer than we would like it to be.” And also, I would also mention throw in Help Desk with Edward as well.
Jay, what do you say on this? I mean, I think Timothy’s take and Edward’s are both on the money.
[Jay Wilson] I completely agree. I really like Timothy’s quote there. And this is how many of us all ended up in security as well. Already. I certainly didn’t take some path that was super straight and narrow onto a cybersecurity role. I bounced around in technology and marketing and somehow ended up in security.
[David Spark] By the way, the paths are like fingerprints. No two are the same. Everyone takes a different path.
[Jay Wilson] Correct. And where there’s a will there’s a way. So, if you really want to be in cybersecurity, find your place in an organization where you have an opportunity to learn something about cybersecurity. It could be adjacent, like one of the earlier quotes said, but the point is go seek it and you will find it, I think.
[David Spark] I love this whole concept of hacking the job hiring process. Have you seen anyone do a great job at hacking the process, Geoff?
[Geoff Belknap] I’ve seen a lot of people do a good job at this, but I want to just pause here for a second and please, implore our listeners, do not take Mr. Pham’s advice literally. Do not send me or Jay a phishing email with malware attached. That’s not what Mr. Timothy Pham is getting at here, right?
[David Spark] No, right. He was talking euphemistically here.
[Geoff Belknap] Yes. Yeah. Do not go the other route. Now that being said, I think this is a really sound strategy, right? So, I started in technology on the networking path, I was doing networking and telecommunications work.
[David Spark] Like what Edward said.
[Geoff Belknap] Yeah, exactly. So, I worked on an IT Help Desk. I eventually worked in the networking space before I sort of pivoted my career to security. But I worked in sales and marketing and all these other things. And honestly, that gives you a lot of a well-rounded experience. Now that being said, you don’t have to do that.
There are ways to pivot into security directly but there are a lot of ways to get into security. There’s risk and compliance, there’s third-party risk, there’s product security, there’s incident response, there’s penetration testing. There’s all kinds of ways to bring yourself into the space. But if you were starting out in music, you wouldn’t go, “I’m trying to get a job as a stadium arena pop band.” Right?
You have to start somewhere else and build into something that you dream about, and you have to be willing to work really hard and try different opportunities. And frankly, trying different opportunities is a really great path because it gives you exposure to all those other parts of security. You may be listening to this right now thinking, “I want to be the world’s best product security engineer ever.” And you may get into that path and decide that that’s not actually what excites you.
You’re excited about incident response or third-party risk, whatever it might be. So, getting into the space in any kind of job is always a great way to grow yourself into what might be a great career for you.
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What kind of experience do you need?
[David Spark] Rodrick Epps of Interstate Batteries said, “Remember experience is experience and it is okay to place on your resume. Projects you’ve done, any volunteer work you’ve done, all counts as experience.” Tania Jareen of Wichita State University said, “Get your hand dirty very early when you are in school, go for an internship, or even volunteer.” I have stressed this as well too.
“Some companies have campuses in the schools and hire students as well.” Deandra S. D. of Georgia Department of Corrections said, “It’s fine if employers no longer want to invest and onboard new/less experienced talent. Since they want you to make the upfront investment in education, professional certification, and sweat equity, be sure to negotiate your salary and benefits accordingly.
Keep in mind these organizations should not only provide you a salary based on your hands-on experience, but also compensate you for the cost of developing yourself.” This is a really interesting angle here because if I’m entry level with no experience and the company’s going to take a risk on me to train me and I may or may not do well, I may or may not like it, so is this all sort of taken into account when you’re hiring, Geoff?
Like, “This person has done all the training and education and experience before they came to me, even though we’re truly their first job, although they have this volunteer and intern experience as well.”
[Geoff Belknap] I don’t know if for the first job this is how companies are thinking about it, but I do recognize, and I hope others recognize, that the base level pay for most people, even in an entry-level cybersecurity role, is pretty significant.
[David Spark] Yeah, it’s high.
[Geoff Belknap] I’m hiring people out of apprenticeship roles and right out of college at more money than I had ever hoped to make when I was entering the workforce, so I think the pay is quite high. It does not necessarily compensate you for all of your college right upfront or all of whatever training programs you’ve taken, but you’re entering a career, and I think over the balance of time you will more than make your money back.
But I do think it is valuable to sort of make sure that the core of Deandra’s message is right. If you are getting into this space, there are two things to keep in mind, and these are absolutely out there, and I don’t want to call them scams but there are things to be aware of. There are programs where you will get paid very, very little money and they will say, “Oh, but you’re getting experience, we’re paying you in experience.” Never take that job.
Never take that job.
And then there are programs that will offer you a little bit of money because they can’t pay a lot of money. Just be very thoughtful about what you’re getting in return. Ask others, ask about their experience, I don’t want to shoo anybody away from this universally because there are jobs, like for example in the government, that are just never going to pay what private sector’s going to pay.
As long as you can get the experience that you feel like you need to pivot into whatever sector or area you want to work in, maybe that’s worthwhile for you. But just be thoughtful about what that is. And overall, I think most people are not trying to scam you or take advantage of you, we’re just trying to pay what we can afford and what the market will bear.
[David Spark] Yeah. Be aware of that. Jay, this whole concept of taking a risk on people that don’t have experience versus people who absorb the experience themselves so making themself look like a less risky hire, I mean, do you take this into account?
[Jay Wilson] No, absolutely. Before I answer your question though, I just want to go back to one thing Geoff just said. And I would say the one category you didn’t hit, Geoff, is sometimes you’ll find opportunities at startups or smaller companies and the compensation is low but the experience and the multi-hat nature of what you learn is very high.
Especially when you’re young, that can be a tremendous boost to your career. So, don’t judge everything by the dollar, especially the younger you are. It can be worth a lot to you.
[David Spark] The best advice I ever got from a mentor on this very issue because I remember I was starting on my own doing my own business and I remember getting my first job, my salary got negotiated down, or my first contract job. And he, by the way, has built many businesses. He goes, “Oh, at the beginning, I don’t worry about the money at all.
In fact, I’ve done things for free.” He goes, “What you need is the stories. You’ve got to be able to tell the stories when you’re there.” By the way, speaking of that, Geoff, I cut you off for a second, has someone, like a green person who wants to work for you, has some experience, have they convinced you with their stories?
[Geoff Belknap] Yeah. Look. I think what Jay is saying is 100% dead-on. I’ll be very clear. My path to where I am today ran through startups. I earned, relative to where we are today at the size of the organization I’m at today, very little money at the beginning of my career. Now, startups are unique in the sense that you’re effectively agreeing for deferred potential compensation if the stock pays out or something like that, but that experience and that exposure, especially at startups are great.
Like you get broad exposure to a broad cross-section of problems that you might not get at a large organization. They are fantastic for developing yourself if you’re a committed learner.
I am always looking for other people that went through that path that have learned on their own. And I’m not saying like went and got a bunch of certifications. I’m saying you took a job, you got a couple of years of experience, you were exposed to a lot of different things, and you’ve got those stories to tell.
And those stories, the things that I’m interested in, are, “I have this experience, and this is what I learned from it, and this is how I grew from that.” That will win me over every single time. And I think that is at the same level as, “I have 20 years’ experience in this space.” If you are broad, I’m just as interested as if you are deep in one area.
[Jay Wilson] Agree completely.
Where are we falling short?
[David Spark] Diane Gandara of Silicon Valley Networker said, “I’d like to see folks brokering an intro for someone and getting comfortable with it. It’s not hard to do, and how weak we are as industry professionals if we can’t do that much to give someone an ‘at bat’ or intro somewhere.” I got to assume that you have made introductions for people in the past looking for jobs.
I mean, it’s kind of what we all do. Now, let me ask you though. It’s tough to do for someone you don’t know who’s really green. How do you handle that situation, Jay?
[Jay Wilson] You have to start looking at potential. The last section we were talking about experience, but potential is the other important factor here, right? What could this person become? How could this person grow? And it’s not always about what’s in it for me, myself, right? Sometimes it’s simply about how can we help move things along, how can I help this person in this one moment.
So, I’ve done this many times and I’ll continue to because it’s simply the right thing to do, to be honest.
[David Spark] Very good point, the looking for potential. And I’ve had this, like, there’s a lot of people ask for introductions, I give them. And a lot that I don’t, I go, “Look. I don’t really know you. I don’t feel comfortable making the introduction.” What is the line? I mean, have you had a similar situation yourself, Geoff?
[Geoff Belknap] Absolutely.
[David Spark] Can you describe that line, if you will?
[Geoff Belknap] Well, I think there’s a couple different layers of introduction, right? If there’s just, “I want to meet David,” and I think that’d be interesting because I’m building my network, sure. If you seem like a reasonable person, like I would introduce them to either of you two. If it’s, “Hey, will you vouch for me so David will hire me?” I need to have worked with you before.
I mean, also that’s a red flag. If I’m meeting you for the first or second time and you’re like, “Hey, will you please vouch for me to somebody?” That’s a little unreasonable.
[David Spark] The amount of first introductions that go to vouch for me, will you partner with me, let’s do business, like, it’s too much too soon.
[Jay Wilson] Well, if somebody came to me and asked me that, I would actually push them back and say, “Look. Life is not transactional. If you want to go into that, go into sales.” This is all about relationships. And frankly, the best salespeople are relationship people anyways. So, this is not like a just a, “Hey, let me get this transaction done with David.
Oh, great, I got a job.” It doesn’t work like that.
[Geoff Belknap] I think this cuts right to the heart of this discussion though, and I think this is so, so important. And I tell everybody who’s new to the space, “The one thing that you’re not going to learn in college or the boot camp or your home certification is you have to build a network for yourself.” And this is not just cybersecurity, although it definitely helps quite a bit here, learn who the other people are in your space.
Meet the other people in your community or your town that are doing jobs that you’re interested in. Now don’t learn them because you want to go hound them to help you get a job, but go learn who they are, learn where they hang out, learn are there meetups, are there conferences, are they all going to a live taping of a CISO Series Podcast because it’s great to meet those people and understand what are they doing, what are their perspectives on the jobs.
You learn a lot about the industry from being part of the community that is associated with the industry, and eventually those people will give you a heads-up when there’s a new job.
Most great jobs are found not from the classifieds or anything like that, they’re from people that will tell you that job is coming available. Even if that job’s going to get posted on LinkedIn, a lot of times you’re going to hear about it a week or two before that happens from a network of people that have gotten to know you, know what your skills are and what you’re looking for, and they will give you a heads-up that opportunity is coming.
That is as good as me going, “I vouch for Jay, David. You should hire him.” But the bottom line is build that network. It is so, so valuable. And even if you’re not a CISO or a senior leader, be willing to help people break into that network. Again, not to vouch for them if you’ve never met them, but at least be willing to introduce them to other people working in the space so that they can have some community and not feel lonely trying to break in.
[Jay Wilson] Yeah. I did a talk many years ago at South by Southwest and our topic was about how we have too much coming at us in this world. But to connect to what Geoff’s saying, we ended the talk with, “Look, you need to be open to the adjacent possible.” And that’s what this is. And there’s so many opportunities that exist with relationship building.
You might just be great friends with that person. You might get a job with that person. Who knows? You might meet your future life partner. You just never know. You’ve got to be open to good things and open to those relationship-building moments.
[David Spark] I cannot stress this enough. The advice I’ve given is just aim to make one connection a day, one real human connection with a person. Just think about it. If you do that one a day, in a year look at how many connections you’ve made. I mean, a month, just look at a month, it’s insane. And people don’t think that way.
I mean, half of the work we have to do for the CISO Series is audience relations. I mean, that is half of my work is maintaining relationships with our audience. And I communicate with them, and my team communicates with them all the time. It’s a key, key part of building a network, if you will.
[David Spark] Now we’re at the end of the show where I ask both of you which quote was your favorite and why. And there’s a lot of great quotes, and this spurred an amazing discussion here. I’m going to start with you, Jay. There’s one that we both talked about, or all three of us talked about. Which quote is your favorite?
[Jay Wilson] Oh, my favorite is, and I agree with Geoff’s comment about the quote, is Timothy Pham’s quote around hacking into the system.
[David Spark] Don’t really do it.
[Jay Wilson] Don’t really do it.
[David Spark] Euphemistically do it. [Laughter]
[Jay Wilson] But I think I connect with it personally because I really do believe that we can go out and get what we’re looking for. Legally, not illegally, please don’t hack. But if you’re seeking this role, if you’re seeking this opportunity, you can go out and get it.
[David Spark] Very good. Yeah, I’m in agreement. You got to just think of it with out-of-the-box thinking, different eyes. Geoff, your favorite quote and why?
[Geoff Belknap] Gosh. Between Deandre talking about negotiating your value and Diane talking about building the network, I can’t pick one. So, I’m going to pick both. I’m just going to take a little bit of liberty here.
[David Spark] Okay, it’s a tie. Well, they both start with the letter D.
[Geoff Belknap] That’s right. I don’t know if that’s why but two things to keep in mind. Definitely be thoughtful about what you’re getting in return if you’re going to take a lower salary. If it’s not everything you hoped for, is it valuable to you in the long run. I think it’s perfectly reasonable to take a job for a year or two.
I think there is no shame in that if it’s an opportunity for you to learn and build some experience. And then I think alternatively build a network. If you are already in the space, you should be helping people build their network. That is, again, not the same as vouching for them and giving them roles, but introduce them to other people that are in the space that they might be interested in.
That is good for you, it’s great for them. Someday they might be hiring you. You have no idea. This space is such a weird place and it’s also the world’s smallest place, so it’s great to be generating positive vibes in the space and being that person that helps pay it forward.
[David Spark] Excellent. Well, that brings us to the very end of the show. I do want to thank SlashNext, a great, great supporter of the CISO Series. We greatly appreciate their support. Really, check them out for all your messaging protection needs. Now, it’s not just email. Email is one of many ways messages come into your system.
And the whole concept of phishing is not isolated to just email. It’s across all messaging apps. So go check out what they’re doing at slashnext.com. And I want to thank you, Jay. I’m going to let you have the very last word. For those of you looking for jobs, Geoff’s company LinkedIn has a great opportunity to do just that.
You can just go to linkedin.com and search for jobs there. I think it’s under the linkedin.com/jobs page or something like that.
[Geoff Belknap] Something. Go to linkedin.com. You’ll find some stuff from there, it’ll be great.
[David Spark] Jay, any last words on the subject? And we always ask our guests are you hiring. Are you hiring?
[Jay Wilson] I’m not currently but hopefully soon. I have [Laughter] some roles I’d like to hire.
[David Spark] So, by the way, make yourself present to Jay. Begin your network with Jay now so when he’s ready there’ll be a great opportunity.
[Jay Wilson] Exactly. My final word that I would add is there’s no bad experience to contribute to a great cybersecurity practitioner. Cybersecurity is about securing businesses, and I say it that way because the business matters. So, for all of us as cybersecurity practitioners, we need to care about those businesses.
Any experience you come with will probably inform your perspective of that business and how to help protect it. So, I don’t look at any experience as bad experience on a resume.
[Geoff Belknap] A great point.
[David Spark] Very good point, and I’m in agreement with that as well. Thank you very much, Geoff. Thank you very much, Jay. And thank you, our audience. We greatly appreciate your contributions and for listening to this very show, Defense in Depth.
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