The Pros and Cons of Cyber Startups: Is a role at a security startup right for you?

So that’s me today still doing matchmaking, a little less from the recruiting angle, but yeah, just kind of keeping my finger on the pulse of the job market in our space. And it’s just obviously an ever changing, such an interesting evolution.

And that’s what we’re going to talk about today a little bit, is the cybersecurity job market right now, but more specifically, an area that Dan and I have been in, and that’s startups. And what does that outlook look like, particularly from the employee perspective? What is it like to work at a startup is the right fit for you? What does it look like in terms of the job market right now in cybersecurity, particularly maybe tech more broadly? We’re gonna kind of spend some time talking about that today with Mimi, since she is an expert in this area and in cybersecurity particularly. I actually met Mimi at a cybersecurity marketing event at Black Hat a few years ago. So, yes, I’d say, as I’m very new to cybersecurity, you have done well meeting all those marketers.

Oh, my gosh, that was the best. I think that was the best marketing money I ever spent, was, I’m getting that suite. I got a suite of the four seasons at Black Hat and basically had snacks and drinks probably three times a day for all the marketers to come chill and hang out. And it was so fun. I mean, people came multiple times. It was great.

Yeah, I did. And it was so welcoming and just a way to get connected with other people.
So, yeah, it was great meeting you. And now we’re here. Well, why don’t we kick it off and talk just a little bit about the cybersecurity job market right now? And Mimi, I’d love to get your take on where we’ve kind of been over the course of the last year, where you think we’re going. Okay.

So it’s interesting. I would say it’s very hard to put your finger on the science of it. There’s a lot of anecdotal instances and a lot of anecdotal data that you can gather from just really talking to a lot of different people. If you want to see things as being horrible and you see all the layoffs, you could see it that way. But I talked to too many people to see such a limited reality.
Um, there’s a lot of hiring going on. I understand. I think you’re doing some hiring. Um, and the hiring is, though it’s more strategic, it’s definitely more risk adverse, I would say there’s a little. A lot of the layoffs, we’re really an over correction from a time where people were just throwing money at hires, hoping that it would solve the pain of the immediate issues facing a company, especially startups. I will say bigger companies as well. But startups had the money to just throw money at problems from a human resource perspective.

So a lot of the layoffs that I’ve taken note of and looked at and looked under the hood at were definitely that it was companies that, as a recruiter, you know, I saw were just sopping up all the good people and, you know, just paying them insane amounts to keep them there. Raises, raises, raises, raises, until, you know, what we have today. So that’s like, my really high level, I would say, throwing in a little positivity to what’s going on, because I really don’t see, I don’t see doors being shuttered. That’s when we would start to say, oh, we’re really looking at a dark time, is when you would see companies really closing down, not companies getting more efficient with their funds and things like that. So that’s, you know, I don’t want anyone to call me, you know, like, rose colored glasses, but it’s real.

Well, you know, and I think from my perspective, you know, we, we experienced, you know, we were in the, in the wave of, like, you know, hey, there’s lots of, just lots of activity in the market. You know, we were fighting for people, you know, as well, you know, in kind of the, the late 2021, early 2022 is when we got our series B funding.

And so I think we definitely noticed that there’s just, like, so much activity. And some of it, I think what I’ve learned through all this is, like, sometimes, like, if it to trust your gut a little bit, if it doesn’t make sense, it probably isn’t, you know, even if you don’t necessarily know all the, all the factors behind it. And I would, I would agree, I think that, you know, a couple years ago, there was, there was an influx of cash into the market. It was money that needed to get invested based on not getting invested in 2020. And it kind of started to build up, and so people started investing money, and founders and startups, they’re like, well, you’re under some kind of, I would say, intrinsic pressure to how you’re going to spend the money, as opposed to what is the, anytime you’re raising capital, a founder is going to be asked, like, what are you going to use the money for? So you kind of have to have an answer to that question. And a lot of times, the best way to spend money in terms of where you truly see it as an investment is people. Right? Like, well, if I bring on people, they’ll help solve the problems that we need to grow. And that can be very dangerous, too, in terms of, like, it’s not just hire people to throw at a problem or just hire people expecting that to, like, translate into immediate growth for a company. And I think that’s, that’s where you saw that, you know, that over correction. Like, there was a large influx of people being hired and now kind of coming back to like, hey, well, this is actually where we should be, right, in terms of, like, our size of a company, right?

Yeah. I mean, I love what you said about kind of following the instinct. It’s one of my core recruiting and job search strategy philosophies, which is that I, you know, like if you want the best book about recruiting and searching for a job, take like any dating book. And it works better for dating than it does. I mean, it works better for recruiting and job search than it does even for dating, because dating so complicated, there’s too much emotion. With job search. It’s the same principles.

Follow your instincts. If there are red flags, they probably are real, but definitely look, because some, right? If it’s a pink flag, that could end up actually being a plus for you. But if it’s a red flag that, you know, then that means there’s a reason. By pink flag, I mean, you know, looking for opportunistic situations where maybe other people don’t see the value, like a Warren Buffett type of scenario for hiring and job search where, you know, you might not be, let’s say for a job searcher, it might not be the hottest company on the market that’s growing like that. But you like the people, you like the problems they have because everybody has problems. You like those problems. They’re problems that you don’t, aren’t afraid of. You’re the best person for that job. So another person might come and not see that as being an amazing job. That’s an amazing job for you.

And on the hiring side, same thing. You see a candidate who maybe isn’t the most technically in demand or isn’t coming out of your competitor, or, you know, whatever it is, hasn’t done exactly the thing that you dream will happen from this hire, but has some very core strengths that, you know, are missing in your environment. That would be an amazing value driven hire for that company.

So it’s a lot of things like that, and it’s a little long winded. But what I wanted to point to is that during the abundant period, people were either ignoring red flags for the sake of wanting something more than they wanted the right thing, or they were ignoring value that they could have maximized on. And that’s kind of where I think we sit now. Red flags are redder than ever and people are terrified of them. At the same time, I think a lot of companies are finding, let’s make a value driven higher here, and people are looking for jobs that make them happy and they’re not, you know, for startups, for example, like, I don’t think people are thinking anymore, oh, is this going to be the startup that’s going to make me rich. They’re thinking, is this the startup where I’m going to enjoy myself? I’m going to be able to build something real?

Yeah. Yeah, exactly. I think that’s, that’s a, that’s a good, that’s a good call out, right? It’s like that. Hey, you know, the, I think my advice to anybody in terms of, and I think even my exposure to on the back end of like, all these, like, you know, the company can still be very, very large and still have a lot of the same issues that a company, you know, that is very, very small has in terms of like, how they’re managing their company, how they’re managing their burn rate, you know, all those other metrics. Right? And so size can be deceiving for a company and even like, revenue can be a deceiving, you know, you know, again, it comes down to like, you know, the biggest can fail if they’re not managing the company well. But like, also, you know, having the notion of like, hey, is this a, is this a good place for me to, you know, further my career and enjoy, you know, the people I’m going to be working with? And, and then the cherry on top would be like, there’s, there’s, there is that, you know, value that I’m having some equity in the company and there can be some, right?

Yeah. Oh, sure. That doesn’t go away. I’m just saying nobody is going to be like, oh, and you might like, no, people will make their own value judgments about that. In fact, drinking the Kool Aid may even happen once they’re in the company, as opposed to needing to feed them the Kool aid in the hiring process. Yeah, exactly.

So, yeah, we’ve kind of got into it. But let’s talk about a few more of the really positive aspects of choosing a startup. Dan, you were just writing on this topic in your newsletter about the market, maybe making a little shift in the positive direction. Maybe we’ll expect to see a little bit more influx of funding and some of those kings bouncing back a little bit, which could result in more opportunities at startups and smaller companies again. So what are some of those pros? What are some, Mimi, when you’re talking to people, what do you see as some of the major benefits of choosing a startup?

Well, the benefits are usually not the benefits. Not always true. But I just felt like I had to say that because you set me up for it. But I think the benefits are, it’s interesting. The benefits are not for everyone. It is true if you’re looking for the illusion, and Dan, I think you’re 100% right. It is an illusion that there is stability with a company who’s on a certain revenue track. I mean, you hear people talking all the time about saying, okay, I’m looking for my next role, and they have to have this revenue. They could have posted that revenue, and tomorrow it’s, it’s millions less than, you know, what they’ve had to last post. So, you know, there’s always illusion when it comes to these things, and everybody really is making their own risk assessment. So I think, you know, you have to be the type of person that can handle quick change, that can change course. So you have to have that as a prerequisite, I think, if you’re going to even be able to handle the benefits of a startup, because, you know, if you, I’ve also seen, I actually wrote a chapter of my book about this, the manic pixie dream girl concept when it comes to, which is like, the idea of, you know, the, this, like, girl in a lot of movies in the two thousands that were the early two thousands that were, like, basically had no personality, but were like, these very whimsical type of, like, oh, what’s her name? Zoe Dashanel. Like, she’s like the typical, you know, and like, she doesn’t really have personality, but she’s whimsical. And everybody thinks that she’s just gonna bring life to everything. So some people see a startup opportunity or an exciting hire as being like, oh, we’re gonna bring some sparkle in life, and it’s this exciting thing, but it has to fit you, or there’s nothing there. You know, it’s really just this, like, fun little fantasy.

So I think that really, the benefits of startup life are the challenges. Just like, you have to really thrive on change and enjoy it. The major thing that is another prerequisite is the ability to take ownership over something that’s not even necessarily your fault. And I find that the people who just, and again, I know I haven’t said the benefits yet, but I’m saying a lot of the things that I’ve seen, people think it looks exciting. So let’s say the benefit isn’t that it looks, you know, let’s just say somebody thinks exciting. Um, you know, if you’re going to blame anyone, or you can’t, you can’t handle taking blame for something that’s not 100% your fault, um, then, then you will always be unhappy, because you’ll always be looking the blame chain is the most toxic cycle of a startup. You know, like sales will blame marketing, marketing will blame product, product will blame, you know, like the core, you know, founders and all these things and then the founders will blame the VC’s and everybody who’s blocking them from doing their dream. So if you are that type, you’ll get caught up in a toxic cycle. But if you can take ownership, that’s the best indicator you will be successful at a startup and be able to benefit from the benefits.

And the top benefit I’ve seen is career skyrocketing. So in a larger environment there’s going to be a lot of people who will be above you or next to you doing things that you might want to be exposed to or that, you know, you could be really good at and it will be considered stepping on toes to even get into it. So I think that that’s what I’ve seen. People just come back to me who’ve, who aren’t lifers, you know, come back to me after, you know, entering startup and just saying, wow, this accelerated my career five years ahead. Something that I would have had to wait for somebody to retire or get fired or quit. So that’s the huge benefit. Yeah.

Oh yeah, totally. And I say like, you know, having, you know, having built a company, you know, having built a startup from the ground up. Right. And it’s funny because like I think everybody that’s like been in any stage of a company, they still consider themselves a startup. Like, I would still consider us a startup even though we’re very well funded and like, you know, have Series B and, but like there’s just so it’s always new. Every, every stage is something different. And I think that’s another benefit is that you get you, if you come in early, you get exposed to like all the different things that go on, right.

And it’s a great learning opportunity just like for growth. And like, you know, Anna can even attest to you. Like you, you end up wearing a lot of different hats than you actually signed on for and that’s that ownership piece too of just like, hey, we’re all on a team trying to figure out how to get it done. It does nobody any good to try and, try and get into that blame cycle. There’s a book that I often talk about in our company and I show the illustration, it’s called the Oz Principle and it has a great illustration about the accountability line where staying above the accountability line is like, hey, as a team we’re going to see the problems we’re going to own, the problems we’re going to solve them and execute on them, as opposed to staying below the line. What I call below the line is that notion of, well, it’s not my job, it’s somebody else’s fault, that blame game thing. And that, that doesn’t do anybody any good.

Right. Regardless of what’s. It’s literally the downfall. I’ve seen startups fall apart. Yeah, yeah. Completely because of that. Just, yeah. Down to the founders who like, weren’t able to see their own part in everything. Right. Yeah, no, exactly. I mean, it’s, it takes some self reflection, for sure, and, and it takes a lot of just fortitude as, you know, coming into an early staged company, you know, that like, hey, you know, there’s going to be good days and bad days and everybody’s going to, you know, cheer and cheer and cry together and so. Cheering and crying, yeah. Look, I think that startups really like to look for people who are not considered job hoppers, which is, you know, a bad term in my world, because especially these days, you never know. But I do think one of something that hiring managers can look at is, was there a time or two where they stuck around? Focus on that and ask them why.

Because if, and I talk about this with a lot of just job search clients and with hiring clients that just because they’ve had a hard go of it for the past few years now get curious about the times that they didn’t, and it’s very likely you could be the next place that they would be able to stick around, if you know why. So, yeah, I mean, I think that people who have that stay with it ness at all in their makeup, there’s something there to look at. Yeah. You have to be able to get hurt, feel sad, and then move along, get back to work. Yeah.

Yeah. So that’s interesting. You mentioned that there can be a lot of opportunity. I think there’s a lot of opportunity not just to learn and grow, but specifically to break into a new industry because you might get a chance that no one else is willing to give you, which is what happened to me. I was in higher ed and nonprofit work doing exactly what I’m doing now. But to break into this industry was, I wouldn’t have had that opportunity without, without PlexTrac taking a chance on me very early when they just needed help. Thanks, Dan!

I want to ask you, and I hope this is okay, just because there is an element that I’ve seen where startups are risk adverse when it comes to hiring somebody from outside the industry. So I hope it’s okay. I want to ask you, when you joined, what was it that was that bridge that they knew with certainty that you would be able to kind of grow into that? Cause I think a lot of people wanna know that. I see a lot of people trying to break in, and I think it requires either a person bridge, but not just a person bridge, because that’s never enough, but also a skill bridge or an experience bridge. And I always recommend people to have both, because then it makes it easy to, for the company to then see the potential. So can you remember back, and maybe even Dan, can you guys remember back to when you were hired and what, what did you know, Dan, about Anna, that, um, that you believe that you felt that the risk was not high, that should be able to get on?

Yeah, I mean, I think that’s a great question. Um, and so hopefully won’t make Anna blush too much, but I think, like, you know, definitely knew Anna from, you know, we, we do go back.
We have, you know, we have a history, but, like, so I’ve known Anna for a long time and know what she’s capable of in terms of just, you know, so I knew, I knew the people, the person that she was right. In terms of, like, being able to, you know, do the research, dig in, you know, you know, figure. Figure stuff out, solve problems. Right. And I think that’s in any higher, like, especially early on, that was the biggest, that’s the biggest thing I always looked for is, like, does this person have the ability to go research and solve problems? Like, you know, I mean, we had a lot of other folks in the company that knew the cybersecurity industry, so I felt fairly comfortable that we could at least guide some of the content as long as we had somebody that could do it on their own, was a good writer, was able to research and things like that. So I think that was the biggest draw. I think that we probably would have been much more cautious with somebody that we didn’t know at all.

Right. Like, but I love what you said, that the experience that you had had, knowing who, who, Anna, you were professionally, is that you were somebody who could research problems. And I think that’s just really so important for people to hear if you have a problem, that you’re not going to become, like, a blocker in the flow. Yeah. And I think people would really. And then I also, like, Dan, what you said, just, I think these are two, like, basically groundbreaking things for people to hear. You don’t, you may not see it as so much, but I think anyone who’s looking, you know, right now to join either you guys or other startups, you know, asking if they have resources of people who, where they might need that training and that the company feels confident.
And this idea that you can show a company that you can research problems, I think that’s huge. It speaks exactly to what we said before about, you know, somebody who’s accountable and can carry things.

And I think from, from my side of that conversation, you know, I had a fairly long background. I taught education class. I mean, I taught at the college level for like 15 years, classes in technical communication. And that’s the thing I was constantly telling students is that your experiences, even if they aren’t directly in what it is that you want to do, you have to connect the dots, because it is really, truly, and now that I’ve been here for a while, you know, doing what I was doing in higher education, selling and promoting and marketing very expensive college experiences for students, isn’t that much different than,

Yeah, you were able to make that bridge and you were able.

And I think it also is about being very realistic about what it is that you do well, where you can add value. So I came in and I was like, okay, Dan, I don’t want to be a marketing director or anything. This is where, these are the areas where I think I can add value to you right now. And, you know, did I end up doing many different things? Yes,

But things that you were so confident in. I love how you said that, that I can do and bring value right now. And that’s another really good guiding principle for people looking is, are the things that you’re good at, what that company needs to solve right now.

I’m not trying to oversell myself because I knew I didn’t want to get in over my head.
So if these were not things that they needed at that point, then, you know, I didn’t want to take that job. I didn’t want to start there.

So that, you know, that ironically, Dan, you didn’t have to even look at the potential as much as you could look at that. The things you needed right now were there. And I think that’s also something that sometimes founders and hiring managers are pressured to see potential, and it messes with their instinct because potential is great on a certain level, but being able to be clear about what the issues are today, what the challenges are, and that this person can address those today with potential for growth. You can deal with that later. Right.

Yeah, exactly. A lot of people hire on a kind of like inflated potential, you know, fantasy idea of something, and I love just hearing a really concrete example of that. And then you took what you could do that day and then you just expanded and grew as you became a part of things. And that’s, that really is sustainable.

I think one other area that I see that may be positive or negative for people that are joining, especially early stage startups, is that you may end up being more of a generalist before you’re a specialist. So if that makes sense, you may end up doing whatever’s thrown at you. I mean, hey, I did a stint in HR for three months and we hired like 30 people. It’s just what needed to be done right then. And so we figured it out and did it. And what a great experience. And do I want to do it again? No, but I learned a lot. And if I had an issue stepping outside of my comfort zone and not doing what the company needed right now, that might have been, that might not be something that someone wants to do that feels like they are really, really, you know, grounded, that they’re, that they’re ready for that very specialist role. Now have I got to move there? Yes, but there were also events marketing, there was, you know, I, and this is on the marketing side, but I imagine it’s probably true for others on the more technical side that it may be a while before you’re a specialist in your area within this context.

Yeah, I mean, I think, I think, I think like the biggest thing early on, you know, and I think that’s where it’s like when we talk about a person coming into a startup and then also what stage the startup is, what stage are you really looking to come into? Because the bigger they are, then they just can’t just go higher for specialties. I need a data science person in this realm, but there’s definitely something to be said about just having somebody that can adapt to a lot of different scenarios from the technical side, depending on how and being able to move quickly and fasten. So I think those are the questions that you have to ask of yourself. Like what kind of examples of that? Oh, sorry, I didn’t mean to, I was just curious, what are some examples of that from a technical side? I don’t work as I, you know, I don’t know as many technical people, but, you know, where, where are those lines blurred where somebody who has, let’s say, this specialty is able to move into other technical realms?

Yeah, I mean, I think you know, without trying to be too technical. I mean, I think, like, early on, you know, we were kind of looking at more like full stack engineers, somebody that can kind of pull them across the entire code base. And then as we’ve grown, it’s like, hey, well, no, we can, we can get specialized in somebody that has a deep background in just the backend or just data science or AI and things like that. I got that.

So. But, you know, early on, you know, and that, again, that’s, that’s where you kind of look for those folks that they may not have all that experience, but can they dig in and research and solve the problem? I mean, truly be a hacker right at the end of the day, which is my background, I mean, like, you know, you get on a pen test and you gotta be able to figure out the technology you’re testing in about a week, or you’re not gonna provide any value to the customer.

Yeah, that’s so interesting. And I assume when you’re hiring, let’s say, a full stack person, you really do have to have that honesty of, like, you’re not getting a full stack person that is a specialist in every single right part of that process. So you have to know your own needs deep enough, well enough to know how to make sure that person can address, like, a really specific, immediate piece.

Yeah, yeah, exactly, exactly. So, yeah, like you said, it’s a balance between hiring for the needs that you have at the time while trying to kind of keep an eye on, like, hey, you know, as we grow, what are we going to, what do we need to kind of keep an eye out for, you know, in 6, 12, two years, you know, six months, twelve months, two years kind of a thing.

Right, got it. Yeah. That’s great. Well, we are, we are, man, almost at time. It’s been a great conversation.I kind of want to wrap it up here, but, Mimi, do you have any final, you know, just thoughts or takeaways on this, on this subject you want to throw out to kind of sum up?

Well, I mean, I love talking to a startup that has the right attitude about hiring because people are looking for that. So, you know, I think it’s, it’s great. It’s great to hear that. And I think anyone who is on this job search right now, in this time, and is falling into, like, the darker perspective space, I think this is just a great example of companies that are hiring that are doing things right, and it makes me feel hopeful, so I hope it makes the world feel helpful.

Well, thank you. And thank you for coming on. I just want to, you know, I want you to give us a rundown of the projects that you’re involved in so folks can find you, use your services. I think you got a podcast going, so why don’t you tell us a little bit?

I’m so excited to. This is actually the first time I’m announcing it. We’re still in the planning of it, but I’m going to be working with the Millionaire Recruiter, Brianna Rooney. And we are going to be hosting a six week Job Search Chiropractics, that’s what we’re calling it. Little tweaks on the search to help you get realigned. And we’re going to be having internal recruiters from some of the bigger companies and some of the really cool smaller companies just to help people make tweaks on their job search. And so that should be coming out. I think we’re going to be doing it in July, so it should be coming out really soon.

And that’s what I’m doing a lot of job search strategy, also hiring strategies. So companies that are looking to maximize their time hiring, just looking at what they’re about to do and making sure that they have the right strategies in line to make it the most efficient and good process that it can be. And of course, I’m with the marketing society close to my heart. And so if you are a cybersecurity marketer and you’d like to be a part of the community, I can send a link and we’d love to have you. And there’s a lot of amazing resources for both job searchers and hiring people, hiring managers. And just in general, if you’re just trying to do your job better, you can network with other marketers and learn a lot. It’s like a very friendly space.

People have planned parties together at RSA through the network just by throwing things out there and seeing who has similar interests in customers. So it’s just a really wonderful community. Thanks for letting me promote it.

Absolutely love it. And follow, follow Mimi on LinkedIn. She puts out lots of great content, great helpful tips and just very encouraging stuff.

So thank you so much for having me.

Yeah, thanks. We really enjoyed it. Yeah, everybody have a great Friday. Happy Friday.