Driving Disruption: Haris Pylarinos of Hack The Box On The Innovative Approaches They Are Taking To Disrupt Their Industries

An Interview With Cynthia Corsetti

Embracing a healthy dose of craziness: Sometimes, disrupting the status quo requires thinking outside the box and embracing unconventional ideas. A willingness to take bold leaps and think creatively is crucial in driving innovation and shaking up the industry.

In an age where industries evolve at lightning speed, there exists a special breed of C-suite executives who are not just navigating the changes but driving them. These are the pioneers who think outside the box, championing novel strategies that shatter the status quo and set new industry standards. Their approach fosters innovation, spurs growth, and leads to disruptive change that redefines their sectors. In this interview series, we are talking to disruptive C-suite executives to share their experiences, insights, and the secrets behind the innovative approaches they are taking to disrupt their industries. As part of this series, we had the pleasure of interviewing Haris Pylarinos.

Haris Pylarinos is the Founder and CEO of Hack The Box. With a vision to connect and upskill the cybersecurity community worldwide, Haris disrupted the industry by introducing Hack The Box to the world, and its innovative holistic 360º approach to cyber workforce development, assessment, and recruitment.

Leading the company’s expansion worldwide, Haris has been managing to grow Hack The Box exponentially. Under his leadership, the team scaled to over 260 employees and over 2.5 million platform members since its launch in 2017. 

In addition to his role at Hack The Box, Haris has over 15 years of experience and expertise in cybersecurity and systems engineering. He also possessed a strong background in Networking and Software Architecture.

Thank you so much for joining us in this interview series. Before we dive into our discussion about disruption, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

My journey was driven by two main goals. Firstly, as a cybersecurity professional, I was driven by a desire to improve my penetration testing skills and think outside the box. Throughout my career, I found that the most valuable lessons came from moments of uncertainty, where I had to figure out solutions on my own. Frustrated by the conventional cybersecurity training methods, which mainly relied on reading materials, I created Hack The Box to offer real-world and gamified simulated environments where professionals could put their skills to the test. 

Secondly, I wanted to unite like-minded people and make training sociable, and fun. That’s why I introduced the community element, turning Hack The Box into a social network for ethical hackers and cyber professionals. A community can provide the biggest pool of knowledge – therefore by utilizing it, you enable everyone to continuously learn and advance. Today I’m proud to say HTB stands as the largest cybersecurity community globally, with over 2.5 million members.

What do you think makes your company stand out? Can you share a story?

Hack The Box’s community is truly one of the standout features of our platform, from its inception to the present day. In the early stages, we even recruited from our community. Take James Hooker, now our CTO and co-founder, for example. He began as a user of HTB in its early days, quickly becoming one of the platform’s top players. Even after completing all available content, he continued to engage, assisting new users and even identifying a vulnerability on the platform. His dedication led him to become an integral part of the team that shaped HTB into what it is today. This is just one example of the unique stories that emerge from our community.

Apart from our large community of over 2.5 million ethical hackers and our work with 1,500 organizations globally, at Hack The Box, we’re all about keeping our focus on product quality and innovation. This helps us stay ahead of market demands and the fast-paced changes in the cybersecurity world. Our team is constantly adding new and curated content every week to create a fully gamified and user-friendly environment. Plus, we believe in making cybersecurity training accessible to everyone, so a large portion of our content is available for free to our community.

What also makes HTB different is unlike traditional upskilling methods, we offer a 360 approach to cyber workforce development, assessment, and recruitment. Our ultimate goal is to provide a single pane of glass for cyber-security experts where they can recruit, upskill, retain, and track their team’s success, whether that’s on the offensive or defensive side.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Firstly, keeping calm amidst the chaos is key. Leading a business inevitably involves tackling crises and making high-pressure decisions. Yet, effective leadership means navigating these challenges calmly, making informed choices, and reassuring the wider team. This is a daily practice for me as CEO, there’s always a fire to extinguish, but I’ve learned to prioritize calmly.

Secondly, I pride myself on being approachable. This quality creates a culture where employees feel comfortable reaching out directly, not only about work-related matters but also about personal concerns. It’s crucial to me to create an environment where everyone feels heard and supported.

Lastly, embracing out-of-the-box thinking has been key to our business’s success. From our business model to our products, we continuously strive to push boundaries and explore unconventional approaches. This mindset has enabled us to stay ahead of the curve. 

For example, our recent CTF (Capture The Flag) shows our commitment to this. The theme is ‘Hacker Royale’, where users are thrust into a dystopian society teetering on the edge of collapse and participants have to think outside of the box and hack to survive and save the world. This kind of gaming environment not only keeps things interesting but also encourages creativity and engagement among participants.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader? I’m curious to understand how these challenges have shaped your leadership.

I’m no stranger to navigating tough decisions, they are an integral part of leadership that shapes my growth. Learning often stems from confronting difficult choices and embracing the lessons from both challenges and failures.

One particular instance that comes to mind occurred in 2022, a year marked by uncertainty and economic volatility for many businesses after the pandemic. Amidst this, HTB faced the need to temporarily halt hiring—a decision that weighed heavily on me. As someone who constantly strives to expand our team with innovative talent, it was a tough call to make. However, it was a necessary step given the circumstances.

Despite the difficulty of the decision, I knew it was vital to guide the company through this challenging period. We made sure to prioritize progressing our product offerings and ensured progress for our internal team. Fortunately, I lead a remarkable team and we have a unique solution that brings tangible benefits to businesses, hackers, and students worldwide, so following that, we quickly regained our momentum despite market volatility.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Let’s begin with a basic definition so that all of us are on the same page. In the context of a business, what exactly is “Disruption”?

For me, disruption is about finding a better way of doing things. It’s about doing something entirely unique. It’s not something you can gather from consumer feedback or research; it’s about chucking out the rule book. That’s at the core of Hack The Box. No one else at the time was offering gamified learning solutions and hands-on upskilling exercises. So, disruption is when you innovate and change the way a market operates. That’s real disruption.

How do you perceive the role of ‘disruption’ within your industry, and how have you personally embraced it? Is it a necessity, a strategy, or something else entirely in your view?

To me, disruption isn’t just a strategy or a necessity. Many successful businesses operate profitably without shaking up the market, they simply provide a much-needed service. Instead, disruption is a mindset. It’s a unique quality that only certain individuals or businesses possess—it’s special precisely because it’s not common. However, disruptive or out-of-the-box thinking can be cultivated. It requires openness to new ideas and a commitment to finding better, unique approaches to doing things, all while enjoying the process.

What lessons have you learned from challenging conventional wisdom, and how have those lessons shaped your leadership style?

Becoming a leader at HTB and challenging conventional wisdom has been a significant learning experience. One crucial lesson is realizing that as a leader or CEO, you don’t need to have all the answers, being a founder often means learning as you go.

Before HTB, my mindset was often black and white, rooted in IT where things either worked or they didn’t. However, leadership requires working with people and facing new challenges daily, demanding openness to continual learning. My journey of growing a company has felt like a fast-tracked MBA on steroids, where you adapt and embrace a fight-or-flight mentality, consistently choosing to lead with fight! It’s been like going through a rapid, hands-on learning process—exactly what Hack The Box is all about. 

Disruptive ideas often meet resistance. Could you describe a time when you faced significant pushback for a disruptive idea? How did you navigate the opposition, and what advice would you give to others in a similar situation?

Oh, there have been a few instances where it felt like the whole world was telling me not to do something, especially with product initiatives! One incident that comes to mind is when a user asked our finance team for a refund after signing up for one of our products because he was getting married and wouldn’t have time for it. 

Our finance team was reluctant to grant this. However, I suggested giving him HTB for free for an extra year as a wedding gift. My colleagues weren’t exactly on board with that after I first suggested it. But, we did it and this user shared the story on social media. It practically went viral, and we gained a lifelong customer.

So, if I were to share advice, I’d say, don’t shy away from disruptive ideas. Disruption can sometimes be as simple as doing something unexpected, like offering a customer a free subscription as a wedding gift.

hack the box team photo

What are your “Five Innovative Approaches We Are Using To Disrupt Our Industry”?

  1. Out-of-the-box thinking: At HTB, I firmly believe in constantly exploring unconventional solutions. My founding principles emphasize finding better and unique ways of doing things, challenging standard practices, and paving our own path in the industry.
  2. Investing in people: I genuinely believe in the potential of our team members and empower them to bring their best selves to work. Everyone has something valuable to contribute when given the chance to shine. By nurturing their growth, I build a team of happy individuals who are dedicated to our genuine vision.
  3. Embracing risk: Disrupting industries inherently involves taking risks. I understand that failure is a natural part of innovation. If I’m not failing, I’m not pushing myself enough. It’s through calculated risks that I pave the way for success.
  4. Building community: Community plays a vital role in our journey of disruption. Whether it’s the unique HTB community of over 2.5m members we’ve created or surrounding ourselves with the right people who share our vision, collaboration, and support are essential in driving change.
  5. Embracing a healthy dose of craziness: Sometimes, disrupting the status quo requires thinking outside the box and embracing unconventional ideas. A willingness to take bold leaps and think creatively is crucial in driving innovation and shaking up the industry.

Looking back at your career, in what ways has being disruptive defined or redefined your path? What surprises have you encountered along the way?

Looking back at my career, disruption has significantly influenced my journey. Success, in my view, is closely tied to disruption—it’s not just about financial gains but about trying to create a unique vision. 

For Hack The Box, disruption means providing groundbreaking hands-on training to create the coolest swag in the industry. Since the founding of HTB, surprises have been constant. For example, meeting people I’ve admired who tell me they admire me has been incredibly rewarding. One of the biggest surprises has been seeing companies I once looked up to emulating Hack The Box’s approach today. It’s a compliment to see them following our lead!

Beyond professional accomplishments, how has embracing disruption affected you on a personal level?

I think the disruption in personal and professional life goes hand in hand. Founding HTB has been a truly life-changing experience. The knowledge gained, tough decisions made, places visited, and people met have all shaped me as an individual. I’m constantly pushed beyond my comfort zone, and I love this as it keeps me growing and evolving.

In your role as a C-suite leader, driving innovation and embracing disruption, what thoughts or concerns keep you awake at night? How do these reflections guide your decisions and leadership?

Ironically, one key lesson I’ve learned is the importance of not letting work keep you awake at night. As a CEO, the day is often filled with putting out fires, but prioritizing which ones to tackle first is crucial. The more fires you handle, the less they affect you overall. This is a lesson I’d share with other leaders—there will always be challenges, but it’s about leading the way and prioritizing what needs immediate attention, that’s the only way you can sleep!

There are always live fires, which one to extinguish first. More fires you extinguish it stresses you / affects you overall. 

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

That’s an interesting question. Honestly, I believe I’m already part of the movement I was meant to start. Hack The Box is more than just a platform—it’s a movement towards better learning and bridging the 4 million cyber skills gap. By democratizing cyber education, we’ve shifted the focus away from traditional degrees to providing a playground for cyber enthusiasts while simultaneously upskilling individuals. It’s a movement towards a better way of learning, and I’m incredibly proud to be at the forefront of it.

How can our readers further follow your work online?

Linkedin: https://www.linkedin.com/in/hpylarinos/?originalSubdomain=gr 

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!

About the Interviewer: Cynthia Corsetti is an esteemed executive coach with over two decades in corporate leadership and 11 years in executive coaching. Author of the upcoming book, “Dark Drivers,” she guides high-performing professionals and Fortune 500 firms to recognize and manage underlying influences affecting their leadership. Beyond individual coaching, Cynthia offers a 6-month executive transition program and partners with organizations to nurture the next wave of leadership excellence.