Humans of HTB #5: Ryan’s Journey into technical operations management

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 to Ryan, who embarked on his journey at HTB as a technical support team lead and now he is thriving as a technical operations manager at our newly created department called Technical Operations.

What was your career path before HTB?

Hi, I’m Ryan! I’m from America, originally from Massachusetts, then Florida, and back to Massachusetts again. Prior to joining HTB, I had a diverse range of experiences. I've worked as an IT coordinator, systems administrator, DevOps engineer, and even ran a technology resale company for a bit. People knew me as a jack-of-all-trades, and I liked to refer to myself as a “specialist in not specializing.” 

Right before joining Hack The Box, I was a student at university, doing some contracting work on the side.

How did you end up at HTB?

I transferred to a new university and moved to Florida right before the pandemic hit. This meant I only had a single semester before all universities shut down and transitioned to online-only classes. Almost everyone from Florida, except my roommate, went back home, leaving me with limited opportunities to meet new people.

With the newfound free time, I decided to focus on improving my practical cybersecurity skills. I became almost obsessed with playing Hack The Box, watching IppSec’s videos, and participating in the community Discord

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I applied for the only available job - technical support, but unfortunately, I didn’t get it due to my time zone not aligning well with the role's requirements. However, I was approached on LinkedIn about two other roles - a sales engineer position available immediately, and an enterprise support role available in a couple of months. I agreed to interview for the sales engineer role.

During the interview, things were going smoothly until the hiring manager asked me why I wanted to be in sales. While I wasn’t particularly interested in sales, I wanted to work for Hack The Box. Despite this, I answered honestly, explaining how I wanted to leverage my skillset to create real value for the company. It seemed to resonate well.

In my mind, the hiring manager's response, “uh huh,” felt like a rejection. Panicked, I reached out to HTB and asked to be considered for the enterprise support role instead. It wasn’t until six months later that I learned they actually liked my answer. Despite the initial misunderstanding, I’m pleased with how everything turned out.

What is your current role at HTB?

Since then, I’ve transitioned through a few different roles within the company: first as the technical support team lead, then later as the technical support manager. Recently, however, I’ve embarked on a new journey in a new department called Technical Operations. It’s an exciting adventure with ample opportunities to contribute to the company's improvement from the inside out, both procedurally and technically. I'm thrilled about it.

Can you share some highlights of your work at HTB?

There are so many things I could list that it’s hard to know where to start. Much of what I am proud of at Hack The Box has truly been the work of my former team, HTB Support, and working with them has indeed been the highlight, even if it sounds a bit cliché.

For more specific highlights, I could talk about what it’s been like supporting Business CTF, where I have regularly interacted with hundreds of amazing organizations and government agencies to help organize the largest business vs. business hacking events in existence. That’s always been both exciting and (the good kind of) stressful.

Then there are all the times I’ve worked at the DEFCON booth or attended other conferences, getting to meet incredible people and make lifelong friends.

Additionally, there are the internal projects I’ve had the opportunity to work on - the automation and internal tooling I’ve developed, and my contributions to the Certified Bug Bounty Hunter

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What are your key learnings from your experience so far at HTB?

I think I’ve learned more at Hack The Box than I have in the rest of my career combined. Every day, I am learning something new. It’s almost impossible not to recognize the incredible talent of everyone here, and there is so much happening internally. Bringing all the pieces of HTB together requires a diverse array of skills, and I’ve been exposed to almost all of them.

I’ve gained a deeper understanding of hacking, of course, but the learning extends beyond that. My technical skills, such as cloud computing, programming, and automation, have improved significantly, as have my soft skills. As a support agent, I had to learn effective communication both internally and externally, efficient troubleshooting, and how to empathize with frustrated customers.

As a manager, I acquired operational and people management skills that I know I’ll use for the rest of my life. One year at HTB is worth a hundred boot camps.

You’ve been at HTB for 3 years now. What makes it a unique place to work?

There’s no company like HTB. I’ve never been to a company that I could even compare to HTB. There are the obvious things - ample vacation time, flexible hours, and the hybrid/remote model. I can’t think of many other companies of this size that would fly all their employees to a Greek island for a week-long, all-inclusive company retreat

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And then there are the less obvious things - the culture, the genuine care people have, the collective belief in our mission. There’s this incredible hacking mindset and an overwhelming volume of talent. Strike up a conversation with a random person on Slack, and you’ll walk away having learned something fascinating.

The most honest answer I can give about what makes HTB unique is that, after three years, I still look forward to working every single day. I genuinely love what I do.

It’s also hard to describe what it’s like to walk around DEFCON or BSides and have someone approach me to express how much Hack The Box has impacted their lives and helped them on their journey in this field. The feeling when someone expresses that sincere, genuine appreciation for the work we’ve done as a company is the best feeling in the world.

What advice would you give to someone interviewing at HTB?

Be passionate. You can teach someone security. You can teach someone processes. What you can’t teach is passion - that genuine eagerness to create cool things, be a part of the team, and grow alongside your colleagues.

When I was hiring, I looked for things that demonstrated real interest. Blog posts about some crazy projects you tried, repositories showcasing your projects, or active participation in the overall community.