Hack The Box is the leading AI-powered cybersecurity readiness and upskilling platform, trusted by Fortune 500 enterprises, government organizations, and MSSPs to build effective cyber resilience and mastery at scale. Through AI-enhanced intelligence, gamified labs, live-fire simulations, and the power of one of the world’s largest cybersecurity communities, it helps teams master offensive and defensive skills in the age of AI through real-world scenarios. Pulse 2.0 interviewed Haris Pylarinos, Founder and CEO of Hack The Box, to gain a deeper understanding of the company.
Haris Pylarinos’ Background
Could you tell me more about your background? Pylarinos said:
“At a very young age, I began experimenting with computers and ethical hacking for the fun of it. This was long before cybersecurity was considered a formal profession. I later pursued systems and network engineering, but my interest led me back to cybersecurity. I wasn’t satisfied with the training options available at the time. They were passive and involved many documents and multiple-choice exams. They also missed the entire point, which is creative, out-of-the-box thinking, building the muscle memory needed to be able to perform in a high-stress environment. So, what did stand out to me was that the best people in security were the people who had spent countless hours actually hacking things, breaking things, fixing them, and learning through experimentation.”
“I have always been passionate about hands-on learning and the ethical hacker mindset. That mindset is what shaped Hack The Box. Today, as CEO, my focus is on making sure we stay ahead of how cyber offense and defense evolve, especially now that AI is transforming both sides of the battlefield.”
Formation Of The Company
How did the idea for the company come together? Pylarinos shared:
“Hack The Box started as a hobby or side project. I built a couple of vulnerable machines, put them online for people to hack them. There was no business plan and no grand strategy to found a company. It grew out of my disappointment with existing learning models, and I wish it had existed when I was learning.”
“It exploded almost overnight. Thousands of people joined, and it became clear that the world was missing a place where people could learn cybersecurity in a realistic, engaging way. Training at the time was too static, too theoretical, and too disconnected from real attacker behavior. Hack The Box was the opposite. It felt alive.”
“That energy is still at the core of the company today. We still have a vision to connect and upskill the global cybercommunity worldwide, helping individuals and teams master cybersecurity and accelerate operational readiness.”
Favorite Memory
What has been your favorite memory working for the company so far? Pylarinos reflected:
“Two moments always stay with me.”
“The first is the early community days. Seeing people land their first cybersecurity job because of Hack The Box or seeing entire local communities form around solving our machines showed me that we were building something meaningful. Some of the most powerful stories come from people telling us how Hack The Box changed their lives. For many, it was working as a pentester and, for the first time, having enough income to create a great life for themselves.”
“The second is much more recent. During our AI vs. Human Capture The Flag (CTF) events, we watched AI agents compete directly with hundreds of human teams. It was a surreal moment. It felt like watching the future arrive in real time, and it confirmed our belief that cyber readiness will become a hybrid of humans and AI working together.”
Core Products
What are the company’s core products and features? Pylarinos explained:
“Hack The Box’s enterprise platform is built to prepare both humans and AI systems for real-world cyber readiness and operations.”
“For humans, our core offerings include:
- HTB Academy: Courses and certifications for red, blue, purple and now AI security roles
- Hands-on Labs and Cyber Ranges, including our Threat Range, which simulates a live attack across SOC, DFIR and threat hunting roles.
- Tabletop and Crisis Simulations that bring technical and business teams together.
- Capture The Flag and Team Exercises that benchmark real capability and drive engagement.
- Talent Search and Candidate Assessment so companies can evaluate and recruit based on proven performance in Hack the Box platforms, not interviews.
For AI, we’ve recently released HTB AI Range: A reinforcement learning environment where enterprises can train AI agents against real-world attack and defense scenarios. It’s the world’s first controlled AI cyber range built to test and benchmark the safety, limits and capabilities of autonomous AI security agents. HTB is actively training AI agents, without dependence on user data, responding to the growing need for continuous validation of AI systems in realistic, high-risk operational contexts where human oversight remains indispensable.”
“The vision is one unified place where organizations train both their people and their AI systems in the same realistic environments.”
Challenges Faced
Have you faced any challenges in your sector of work recently? Pylarinos acknowledged:
“The main challenge is speed. Everything in cybersecurity is accelerating, and AI has multiplied that speed again. Attackers now automate reconnaissance, phishing and vulnerability discovery at a scale that humans alone cannot keep up with. At the same time, the traditional training model has not changed in over a decade. Annual courses are not enough anymore.”
“The biggest challenge is balancing speed and quality. Quality is king. AI has multiplied the velocity of threats, but we are focused on setting a high bar of realism and integrity. While others may rush to integrate AI, we ensure that we are delivering thousands of environments and the highest quality content to more than 800 enterprise and government customers, but also pressure testing the content quality with more than 4 million registered Hack The Box users.”
“We responded to this challenge in several ways:
First, we made our platform gamified, engaging, and fully continuous. New labs, ranges and content drop every week, so teams are always training on current threats.
Second, we embraced the hybrid future. Rather than treating AI as a bolt-on tool, we built environments where humans and AI can learn and operate together.
Third, we invested heavily in realistic blue team (defensive) cybersecurity training. Security Operation Centers (SOCs) cannot rely only on theory. They need to practice with the noise, ambiguity and pressure of real incidents, and that is exactly what Threat Range delivers.
These changes allow our customers to stay ahead of an environment that is moving very fast.”
Evolution Of The Company’s Technology
How has the company’s technology evolved since launching? Pylarinos noted:
“Hack The Box started with a simple idea: give people something real to hack. Over time that evolved into a leading AI-powered cybersecurity readiness and upskilling platform, trusted by Fortune 500 enterprises, government organizations and MSSPs to build effective cyber resilience at scale.”
“We expanded from offensive content into deep defensive and SOC-level training. We introduced team-based cyber ranges that mirror real operations. And now we have added AI systems into production. At Hack The Box, we were experimenting with AI before it was cool, advancing AI-driven learning paths, labs, and research, and we are consistently years ahead of what is to come. For example, we have developed Quantum Computing challenges, a technology that is not yet available in the broader market.”
“One of the biggest shifts is how much intelligence sits under the hood. Our platform maps skills to frameworks like NICE and MITRE, personalizes learning, analyzes performance, and, through technologies like MCP (Model Context Protocol), allows AI agents to interact with our content just like a human user would.”
“Hack The Box is no longer just a hacking platform. It is a cyber readiness platform. And, we will continue to plan years ahead to meet what’s coming next in cybersecurity.”
Significant Milestones
What have been some of the company’s most significant milestones? Pylarinos cited:
“A few milestones stand out.
1) Growing the global community to more than 4 million members. That validation from the grassroots is incredibly powerful. And, as I mentioned, we serve more than 800 enterprise and government customers, including many Fortune 500 companies.
2) Crossing 50 million dollars in ARR with a 65% compound annual growth rate while staying capital-efficient and profitable. We reached this milestone spending less than our Series B round, which is exceptional in this industry and also shows the enterprise need is real and growing fast.
3) Launching Threat Range and bringing high-fidelity SOC training to the market. Running some of the world’s largest AI cybersecurity competitions and releasing the first AI Range for benchmarking AI agents in realistic environments. AI Range goes beyond benchmarking. It enables reinforcement learning in a secure environment where agents play in our labs as humans would. That is a major step toward defining the future category of human AI hybrid operations readiness.”
Customer Success Stories
When asking Pylarinos about customer success stories, he highlighted:
“We serve many of the Fortune 500, including Autodesk, Booking Holdings, Emerson Electric, Raytheon Technologies, State Farm Insurance, Toyota, Verizon.”
“A strong example of a customer success story is Autodesk, a global software corporation that has helped more than 100 million people design and make a better world. They wanted a scalable, hands-on training program for their security teams. By moving to Hack The Box, the company saw a 60% increase in learning activity and created structured pathways for role development. They used HTB’s Capture The Flag events as part of internal training, which drove collaboration across diverse roles and enabled engaging, real‑world skill development.”
“Many large SOCs and MSSPs now use Threat Range as a quarterly operational readiness exercise. Teams work on realistic intrusions with real tools, under real-time pressure. The results help leaders understand exactly where their gaps are and how to improve.”
“What stands out most is how teams begin to think differently after training with us. They become more curious, more adversarial, and more collaborative. That cross-functional mindset shift is as valuable as the technical skills themselves.”
Funding/Revenue
Are you able to discuss funding and/or revenue metrics? Pylarinos revealed:
“Yes. Hack The Box has raised roughly seventy million dollars, including a $55million Series B led by Carlyle. We have passed $50 million in ARR, and spent less than $50 million to get there, showing high capital efficiency. That puts us in a rare position where we can invest heavily in the future without needing constant capital.”
Total Addressable Market
What total addressable market (TAM) size is the company pursuing? Pylarinos assessed:
“We target two converging markets.”
“The first is cybersecurity training and workforce development, which is already a multi-billion-dollar global industry and growing fast.”
“The second is a new category forming around AI agent training and AI security readiness. Every enterprise and every security vendor will need to train AI models and agents in safe, realistic environments. This will become a massive market over the next decade.”
“Together, these opportunities form a multi-tens-of-billions market. Our goal is to lead the combined space and to be the platform where both humans and AI prepare for the future of cybersecurity.”
Differentiation From The Competition
What differentiates the company from its competition? Pylarinos affirmed:
“Three things.”
“First, scale and validation. As you now know, we serve more than 800 enterprise and government customers, and we also have more than 4 million community users across the world. That scale helps us pressure-test our content in real-world conditions and gives us a continuous feedback loop on what works, what does not, and how attackers are evolving.”
“Second, realism and quality. Our content is not theoretical. It is hands-on, high-fidelity, and built around how people actually learn complex skills through practice and repetition under pressure. It’s been tested at scale and built with input from one of the largest cybersecurity communities in the world.”
“Third, our vision for AI. Most training platforms treat AI as a simple helper. We see it as part of the security team of the future. Our AI Range, AI CTFs, and AI Red Teamer curriculum put us in a unique position to shape how human and AI agents train and operate together.”
“These core elements, along with our vision for a hybrid future, form a moat that is hard to replicate.”
Future Company Goals
What are some of the company’s future goals? Pylarinos emphasized:
“Our goal for FY26 is clear. We want to be the global leader in cyber readiness for a hybrid human and AI operations future.”
“On the human side, we are expanding Threat Range, accelerating blue-team content, and introducing new reporting frameworks that help CISOs measure continuous operations readiness, not just training completions.”
“On the AI side, we will grow AI Range, establish it as a gateway for secure enterprise adoption, deepen our partnerships with AI labs and security vendors, and continue building the standards for evaluating and training AI agents safely.”
“And we will keep expanding globally. The demand in the US and Europe is strong, and we will continue building our partner ecosystem so customers can bring Hack The Box into whatever environment they operate in.”
Additional Thoughts
Any other topics you would like to discuss? Pylarinos concluded:
“The main message I always share is that cybersecurity is a team sport. It is not just red or blue. It is not just humans or AI. It is the combination of people thinking creatively, working together, and using the right tools to stay ahead of attackers who are evolving just as fast.”
“Our mission at Hack The Box is to build those teams. To give them the environments, the challenges, and now the AI capabilities they need to be ready for whatever comes next.”
“And we want the learning experience to be engaging and memorable. When people enjoy the process, they learn faster, retain more, and become better operators. That is the spirit of Hack The Box, and it always will be.”
