Humans of HTB #12: Tassos's journey into engineering

Step into the vibrant world of the Humans of HTB (HoH), your behind-the-scenes glimpse into the growth of our talented team and dynamic culture!  

In this HoH series, we talk with Tassos about his journey at HTB as a director of engineering.

Tell us a little bit about yourself. 

Technology has always been my domain of expertise, especially where it intersects with security. I began my career by developing desktop applications for security purposes using Delphi and later transitioned into web development. My interests have always blended engineering and security, so when I discovered HTB, it immediately felt the right fit.

At the time, I had built a doxing tool to generate email addresses, which I used to reach out to as many people at HTB as I could. Eventually, I received a reply from ch4p, our Founder and CEO, who encouraged me to apply once a position opened up. A few weeks later, after a brief interview, I received an offer.

I joined as a junior engineer in 2019, and it was the best decision I’ve ever made!

Could you share more details on your progression with HTB?

When I joined HTB the team was just 10 people strong, and I was the second engineer onboard. With both our CEO and CTO being deeply technical, I learned a great deal from them thanks to their expertise and seniority. I quickly began working on more advanced code, and within two years, I was contributing to two major product lines—HTB Labs and CTFs—while also leading key projects, such as our transition to Vue.js 2.

As the company scaled following our Series A funding, it became clear that it needed a more effective structure, including defined leadership roles. Given my experience and the responsibilities I had already taken on, stepping into a leadership position felt like both a natural progression and a recognition of my contributions.

Later, I chose to return to an individual contributor role. It wasn't a calculated move; I simply had a strong desire to keep learning and took the opportunity to work on complex, cross-cutting projects that impacted all product lines. This shift allowed me to deepen my technical expertise and explore new areas.

Eventually, I stepped back into a leadership position as Director of Software Engineering. This decision was driven by a sense of responsibility to support the team. Having previously guided engineers into leadership roles, I was inspired to replicate that success across more teams and help others grow as I had.

Given your strong technical background, how do you feel about stepping away from hands-on technical work as you transition into a leadership role?

I do miss the technical aspect. It's something I’ve always excelled at and felt naturally drawn to. However, I’ve shifted focus to a new and equally compelling challenge: leading large technical teams and enabling their growth and success. This role still engages my technical mindset, but in a different way, allowing me to grow in areas I hadn’t explored as deeply before.

Could you elaborate on what leadership means to you?

For me, leadership is all about empowering others to write the best possible code they can. I see my role as serving the engineers who are doing the real work.

I focus on creating an environment where engineers can thrive. That means removing obstacles, taking on less technical tasks like planning, and reducing context switching so the team can stay focused and productive. 

By supporting them in this way, I help them stay focused on their priorities and deliver effectively.

What kind of support did you receive that helped you grow in your current position?

I received support from everyone, not just my manager. If I had to highlight two key factors that contributed significantly to my growth, they would be safety and flexibility. 

HTB had safeguarded the working environment—offering a fair training budget, various other benefits, and fostering a culture where competition stays external, teamwork thrives, and trust from the executive level prevails, which allowed me to fully focus on my responsibilities. 

On top of that, I was given clear goals and I had the autonomy to decide, which empowered me to take ownership and drive my success.

How do your personal qualities align with the culture and values of HTB?

When I think about HTB’s values and how they align with my own, a few key themes come to mind. 

First, I’ve always embraced the growth mindset as I enjoy learning new things and taking on new challenges.

When it comes to teamwork, I focus on optimizing systems and processes by staying open to different perspectives and setting aside my ego. This approach helps me collaborate effectively and fosters genuine collaboration to achieve the best outcomes.

In terms of the hacking mindset,  like most engineers, I enjoy problem-solving. It’s about being resourceful and using all available tools to get the job done, and it’s a mindset that drives me every day.

Finally, passion is at the core of everything I do. If something excites me, I pursue it wholeheartedly. That’s how I ended up at HTB when it was still a 10-person company. I wasn't concerned about the salary or the company's legitimacy. What mattered was the intersection of cybersecurity and software, and I jumped at the chance.

Can you name a few recent projects you and your team have worked on that you're most proud of, and explain why?

The ongoing microservice transition is a milestone I'm particularly proud of. This significant initiative brought the whole engineering team together, as it impacted every product line and platform. It gave me the opportunity to connect with everyone, facilitate architectural conversations, and rethink how we operate as a team.

We began with Single Sign-On (SSO)—HTB account in our terms—and then expanded to other centralized services. After gathering requirements and insights from all teams, I had to manage the complexity of the transition and turn it into a meaningful, feasible plan, while communicating and aligning people and teams.

The culture and values of an organization truly shine in difficult moments. What challenging situation stands out to you when a leader acted in alignment with HTB values?

I have plenty of examples, which is great, but I’ll focus on just three!

Let’s take the example of a high-traffic event: thousands of users join at once, something might go wrong. And yet I still feel supported by the way everyone rallies together. 

It gives me a sense of safety and confidence that I’ll get the help I need and that the issue will be resolved.

In another case, a security issue arose after a release. Fortunately, our team stayed vigilant and quickly connected the issue to one of our features. Instead of assigning blame, our senior engineer took charge by launching an incident response and coordinating the team’s efforts. This leader took full ownership of the problem while empowering others to help. We promptly released updates to secure our services, maintaining our strong commitment to security.

As a leader, there comes a time when you need to address underperformance. I was proud to see that all the leaders at HTB, not just one, immediately choose to support those struggling rather than ignoring them or treating them as problems to be ‘dealt with’. 

In these situations, it's essential to acknowledge the reality with honesty and humility, while focusing on helping the team members to get back on track. At HTB, this is the approach we strive to take and we do that through goal setting, frequent communication, and ongoing guidance.

Thinking about the software engineering team at HTB, what kind of engineers thrive here? What skills and mindset are important for someone interested in joining the team?

For me, accountability and ownership are the most important traits. You don't wait or merely identify issues; instead, you focus on delivering. Regardless of the project—whether it's challenging or straightforward—successful engineers have the drive to improve and shape.

Being a cybersecurity enthusiast is also a huge plus, as it aligns with our industry and products. We prioritize secure coding because our users are hackers, so we're constantly tested by the best!

How do you and the broader leadership foster passion and collaboration within the engineering team?

It all starts with clear goals. When the team is aligned on what we’re working towards, it naturally fuels passion and purpose. That’s why we invest a lot of time and energy into ensuring alignment—because it sets the foundation for everything else.

Collaboration thrives in environments where communication is open and intentional. We’ve built regular rituals like stand-ups and monthly planning sessions specifically to foster this. These touchpoints aren’t just for coordination—they’re opportunities to reflect, align, and grow as a team. Whether we succeed or face setbacks, we move forward together and celebrate the journey as one.

Lastly, we consciously steer away from comparing individual contributions. That kind of environment can easily become competitive in the wrong way. Instead, we focus on optimizing team performance because real progress happens when we move forward together.