Hacking the Code: Kyle Hanslovan

When Kyle Hanslovan was at the peak of his game as one of the National Security Agency’s (NSA) finest cyber warfare operators, he could hack just about anything. “I don’t recall a time I ever said that I couldn’t get into that network,” Hanslovan tells The CEO Magazine.

From firsthand experience, he knew that there was a fairly big gap in the range of cybersecurity products that promised perfect prevention as well. He may have spotted an opportunity in the market, but he had also identified a problem.

“I knew that if I tried to directly challenge the plethora of tech titans in the space, who were well-funded with millions of dollars of marketing budgets, no-one was going to hear me through the noise,” he reveals.

“I might have been technically savvy, I just didn’t have a reputation, and some of these companies had thousands of customers and multi-billion dollar market caps.”

Yet he quickly figured out a workaround.

“I knew there was value in finding things that slip past these preventive products — past hackers like me,” he says. “I knew I could make a difference for companies who couldn’t afford my talent.”

In 2015, Hanslovan co-founded Huntress, along with Chris Bisnett and John Ferrell, to offer small and medium-size enterprises (SMEs) the level of threat protection usually reserved for big business. Right from day one, the company’s approach has been, as he describes it, “unconventional”.

Beyond its mission of delivering such high-level expertise at an affordable price, there was the small matter of location. Rather than Silicon Valley, the trio were based on the East Coast and made Ellicott City, Maryland their headquarters.

And from day one, the company has been fully remote – Hanslovan himself calls Jacksonville, Florida home.

Pushing the Envelope

What else sets Hanslovan apart? His background.

“I’m a bit of a career rule breaker,” he admits. “I’m somebody who likes to push the envelope.”

Growing up in a low-income family, Hanslovan says he has always been “as scrappy as hell”.

“I’ve always had some sort of side job, side hustle, side gig, whether it was doing computer work or mowing lawns,” he explains, adding that whatever he was doing, there was one constant. “I always tried to work smarter, not harder.”

After studying computer science at the University of Maryland, he joined the military in 2010. The side hustles, however, didn’t stop.

“You don’t make much money in the service. So I ran small side hustles. It was also a way to grow my skills,” he reveals.

Everything from PC repair to website design and what he describes as “shady things”, such as hacking and ‘modding’, were fair game.

“I guess we started getting into things like finding ways around all the content restrictions of being able to support pirated bootleg games,” he recalls.

 

It may not have been fully above board, but the skills would set him up for the next steps when he decided to leave the military after a decade supporting defensive and offensive cyber operations in the United States intelligence community and Air Force.

“Since my background is in computer science, I had actually gone and gathered the core foundations of computer science and data science,” he says.

In addition, through his side hustles, he had started to teach others how to hack through speeches at major cybersecurity conferences and even won the World Series of Hacking (DEFCON CTF).

“I ended up having all the right skills to be able to begin a startup, which is a combination of vision, how to build products, how to make sure that whatever I did produced money and that the money was worth my time away from all those side hustles,” he reflects.

“It was kind of like the perfect background to launch a startup.”

Targets of Opportunity

In June 2024, Huntress hit unicorn status after raising US$150 million in Series D funding to value it at US$1.5 billion-plus.

It currently protects more than 150,000 businesses (and millions of employees) across the Huntress Managed Security Platform – a single dashboard that protects endpoints and Microsoft 365 identities. Behind the scenes, Huntress Security Operations Center detection and response analysts work 24/7.

According to Hanslovan, hackers don’t care where they get paid from. But the way they target SMEs is different to big enterprises.

“What they’ve done is that they mass automate their operations against these SMEs. What that means is you’re not ever really a true target. You’re more like a target of opportunity where they’re just blasting things en masse and using tons of automation,” he explains.

“It’s only when they get in do you actually get somebody who’s kind of my equivalent of skill really messing you up.

“What’s different to a large enterprise is that it’s a little bit more targeted, a little bit more focused. But because it’s so broad, these SMEs don’t usually have a breadth of cybersecurity talent to do what’s been asked of them.”

Hanslovan explains that the strategy has never been to custom-build the equivalent of a Formula One car and team for these businesses.

“But we can build a sports car that your most junior talent can then help set you apart,” he says.

“What we do is we layer enough of these capabilities on top of each other so that even though it’s not the same as a Formula One car, where everything is unique and everything is top performance, we layer capabilities in a way that you can’t see through any holes.”

This allows businesses to still thwart the majority of risks that are targeting them at their price point – and without having to hire anyone in house.

“Since our product is fully managed and doesn’t ever require human expertise, that is a huge relief when recruiting and retaining talent,” he points out.

More importantly than that, however, is the total cost of ownership.

“We deliver world-class human experts and enterprise expertise at the price of an affordable product and make it attainable and understandable for SMEs. It’s something nobody else can match at our cost of ownership,” he says.

Or to draw back on the Formula One analogy: “We’re able to deliver Ferrari sports car performance that doesn’t require a pit crew, doesn’t require custom manufacture of parts or heavy, intensive labor. Anybody, even the most junior IT practitioners, can use Huntress and it’s a huge differentiator.”

Building a Unicorn

Unicorn status tops a thrilling nine-year journey of learning for Hanslovan and his team.

“My growth story was trying to learn how to build a software as a service company,” he says of Huntress’ early days.

His first step was to turn to a startup accelerator. “It taught me a lot about the business of scale,” he explains, adding that it was there that the seed of Huntress’ first three key growth milestones were sown: bootstrapping the product.

“We spent several years making sure that the money we put into the company was from what we were getting out of it, as well as a lot of our own personal investment,” he remembers.

The second was triggered by the realization that most small businesses didn’t even have their own IT departments.

“I was calling these companies, pitching them my story about how I was this great hacker, who had won the World Series of Hacking, how I had created this technology and that I wanted to help them out,” he says.

The feedback, most often than not, was that most small businesses outsource IT. Aware that there was no way for him to virtually knock on the doors of the millions of businesses that fell into this category, he considered other approaches.

“I thought that if I could find an IT outsourcing company that might have anywhere from 20–100 businesses on their client list, I could go and reach a hundred of these SMEs through that one-to-many strategy. That was a massive milestone,” he confirms.

The final milestone came later down the road, when Huntress had grown to around a US$40 million business.

“As I listened to my partners, I saw that they were having a lot more problems than I expected,” he admits. “It wasn’t just on their laptops and servers. They needed help educating people, preventing their employees from doing silly things. They needed help protecting their digital identity.”

That was how it dawned on Hanslovan that there was huge potential for Huntress to be more than a single-product company.

“We could expand to be a platform and use that same playbook we did on endpoint security for laptops, workstations and servers across all kinds of different things, such as for employees’ identities and for their data,” he explains.

Blind Faith

Hanslovan knows that the decision to target a very different market segment, the SMEs of the world, has required a significant amount of self-belief.

“Usually multibillion-dollar companies are made two ways: selling to consumers like Apple with the iPhone or selling to enterprise, big business, Fortune 500 and Fortune 2000,” he says.

“It’s not as sexy selling to these companies, which most people don’t even think about, although they’re the backbone of our economy.”

Therein lies some of the greatest challenges he has faced building Huntress.

“None of the investors from 2015 until 2019 even believed. Even when I raised my first round of investment, my Series A, that was about US$18 million,” he reveals, adding that he also had dozens of rejections.

“I probably had 70 nos – people telling us we were wrong, we got it off base, that we shouldn’t be fully remote.”

The turning point came in the wake of the COVID-19 pandemic’s spread across the world.

“You can imagine that it was almost fun not only showing people we had the go-to-market strategy right for this unique segment, price point and product, which is giving businesses so much value without requiring them to have expert staff, but also that it was OK we weren’t on the West Coast and that we were remote,” he says.

What kept him going, however, was one particular thought.

“I knew we were making money. And people don’t pay for something that they don’t like, especially when it’s repeating and recurring every month,” he notes.

“Even if others couldn’t see it, that’s what gave me blind faith. I knew one day the numbers would be large enough that they would have to eat those words.”

June’s US$150 million Series D funding was one such moment.

“I didn’t need the money. What I needed, though, were people who believed just as much as I did as I prepared it to be a public company,” he adds.

Peace of Mind

Hanslovan is drawing upon these rock-solid foundations as he looks toward the next milestone.

“We’re preparing to be not only a multibillion-dollar company, but also potentially grow multibillions of dollars in revenue,” he asserts.

“Right now, we work with 150,000 SMEs. In that figure, there are so many different ways hackers try to go after them, how they try to extort money or sometimes just take their productivity down.

“Think about it. If someone goes and prevents you from running payroll for two months, I bet the majority of employees who aren’t in leadership roles can’t make it that long. They don’t have those types of coffers.”

Such scenarios have meant Hanslovan has started to consider how broad Huntress can be.

“My biggest area of current focus in the business is expanding the addressable market to protect more of it and take away the risk,” he says.

Much of that centers around becoming its industry equivalent of the likes of Uber and Airbnb in the sense of building out around its two-sided market model.

“Take Uber; there are drivers and then there are riders, but ultimately it is providing convenience, matching them to transport or a food delivery,” he says. “And for Airbnb, where you have to have places to stay and people willing to stay in them, one of the biggest things they’ve got right is providing experiences.

“I would say Huntress’ version of that is we not only connect and enable businesses with IT and cybersecurity experts, we also provide peace of mind. This allows somebody, after a long day, to focus on their kids or themselves and take care of their own personal health and journey, instead of worrying whether a hacker is going to steal their data or dump their information on the dark web.”

That concept – peace of mind – is what is driving his vision of Huntress’ future.

“Think about peace of mind for your health – it’s about knowing, even if the worst happens, that problems would be discovered early enough and with enough treatment options available to allow you to make it through it,” he says.

“My plans for the future continue to focus on what new products I build, not just in terms of detecting and chasing down hackers, but how we harden the networks to prevent people getting in, and help them with their security posture management.”

On the flip side, Hanslovan also wants to ensure that when something does inevitably turn up, the response in recovery is as seamless and painless as possible, and has them back up and running as quickly as possible.

“Because cybersecurity really is like health. If somebody told you, ‘I’m going to prevent you from getting sick’, you would call them out. It’s the same in cybersecurity,” he says.

“If somebody’s telling you that they are going to prevent you from getting hacked, even the best – even the Huntresses – can’t prevent that.”

His vision for the future of the business is that it is able to restore any damage automatically.

“Or if you took a financial loss, that there’s some blending of cyber insurance into the package where we start guaranteeing our work so that we’ve got you covered, even in your worst days. Because that’s what I would want as a business,” he adds.

A Bottom-up Vision

Hanslovan knows that much of the reason Huntress has enjoyed so much success is thanks to the people the Founders have surrounded themselves with.

“I’m very much a bottom-up leader,” he reflects. “I firmly believe the C-suite is only in charge of establishing vision. The people who execute the vision come from the bottom up.”

It was a leadership lesson shared by one of his earliest mentors in the Air Force, who told Hanslovan, “To be a good leader, you must first be a good follower.”

“That means you have to close your mouth and listen,” he says.

This, combined with an environment that supports belonging and transparency, is crucial to his leadership philosophy.

“It’s about making sure that no matter where somebody comes from or what their perspective is, they feel like they can work in an environment where they belong, even if there are differences,” he muses.

Hanslovan appreciates diversity, equity and inclusion is a hypermetric, but he is also aware from experience of the strengths that come from diversity and perspective.

“It turns out people growing up in an environment where, like in my case, they were poor and scrappy can make decisions that are financially responsible without being conservative,” he says.

He adds that diverse perspectives, whether from gender, race, religion, career pivots or any other metric, allow for good leaders who think about things differently and who help avoid failure.

The Ripple Effect

Hanslovan’s journey to the C-suite has been unconventional, but he wouldn’t have it any other way.

“This work, and the way I build products, makes me happy,” he reveals. “I love knowing that the skills I once used to protect national security are now used to protect those businesses that are the most vulnerable.

“It brings me major satisfaction knowing I’m doing something that is giving back more than I can take.”

The word ‘legacy’ may be a premature one, but Hanslovan hopes that whenever he decides to hang up his boots, people remember that he brought – and left – it all on the battlefield. “The cyber battlefield,” he says with a laugh.

“I hope I’m remembered for giving back way more than I took,” Hanslovan reflects. “Sure, I’m benefiting financially from my company, but I’m also delivering tremendous value to my customers and that helps me sleep easily at night.”

What will make his mission complete, however, is the impact he has on others.

“If you think about me as a rock that’s being thrown into a lake, the splash I make is cool, but I want my legacy to be the ripple, and not just for the people that I’ve improved and helped their businesses, but also my teammates,” he says.

“I hope every teammate that I bring into the company goes off and really crushes things in their lives. I’m pretty excited about that and keeping it going.”