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“Cybersecurity is sensitive and extremely conservative” – Oliver Sild of WebARX

Updated on August 17, 2021

6 Min Read
Oliver Sild interview

If you are a regular reader of our blog, you must have read tons of blog posts and interviews about WordPress security. Security is paramount for the success of any online business, and thus it is important to understand the potential threats and your options against these attacks.

Who can educate us better on security than THE EXPERT himself? Today, we are lucky to have Oliver Sild who will be sharing his interesting story and valuable insights in this interview.

Cloudways: Thank you for your time. Let’s begin with an easy question 🙂 Tell us your story. 

Oliver: It all goes back to the time when MSN was a thing and when I spent a lot of time gaming. I was really into a specific MMORPG game, where I eventually got promoted to the game moderator position. Later I decided to run my own private server of the game (very old game, abandoned by the original developers). I was 15 years old at that time and instead of playing the game, I spent most of my time on the CentOS command-line.

Since there was competition between the private servers, I had to build a website to differentiate my server from others. Eventually, I had to protect it from rival servers as attacks were a common thing to win over players from one server to another. That was when I really got into security since RFI was a common thing back then and many sites had this issue and I also had to protect the server from DDoS attacks.

That grew into a deeper interest in security and I went to study computer networking. Since I already had my experience with Linux servers, networking, and web app security. In the second year of my studies, I was invited to volunteer in military exercises under the Estonian defense league within a small cyber unit. That gave me a wider and more professional overview of what is going on in the cyber-security field in general and over the years I was actively participating in many exercises.

Cloudways: When and how did you choose a career in web development? Who inspired you in the early days and what challenges did you face while starting-off? 

Oliver: At the time of my computer networking studies, I built a small site that would collect all the homework from the people who studied the same curriculum. I built it together with my classmate who was responsible for frontend while I built the backend. Next up, we founded a small web development company together with a focus on building secure websites.

Back then we used Joomla a lot. We made sure that the software was updated and that the installation was hardened against the attacks. In short, we did as much as possible during the development process to make sure the sites we build remain secure. In addition to this, we actively reached out to website owners whose sites were already hacked or had signs of unwanted/malicious content on the site.

I’m not sure if I really had a specific inspiration that made me pursue all that, but I think the motivation was mainly coming from inside.

It’s also good to think back and remember that when I started out, I did most of the stuff wrong. With the first web development company, we did poor bookkeeping, hired friends, didn’t price the services correctly (we offered extremely cheap plans). But then again, I was 18/19 when I started out and this was my full-time job, so I had to learn and act fast.

Cloudways: You are working with computers from an early age. When and why did you switch from web programming to network programming and cybersecurity?

Oliver: I’d say I switched from networking to web development and eventually to entrepreneurship. I’m still actively planning the product development, but for the past years, most of my time has gone to building a strong team, developing company vision and strategy. I constantly learn about new things, keep myself up to date with the latest cybersecurity practices and tech. The truth is, you can’t build good technology if you can’t sell it and make it earn money (that you can invest back into product development).

Cloudways: Who came up with the name WebARX and why did you decide to switch from a web agency business to a cybersecurity business?

Oliver: We decided to switch to 100% security in 2015. We applied to an idea accelerator program where we worked on the idea with experts from AVG (now Avast), Microsoft, and more. The program was for 3 months. It was natural for us to do the switch, as we saw what is happening with WordPress. It was becoming so popular and how the defacements and infections were heavily on the rise. We decided to build technology that other agencies could use to build secure sites for their customers.

We came up with the name pretty much at the end of the accelerator program. It’s a combination of Web and ARX (arx means citadel in Latin). When you imagine a castle, it is a big building consisting of many houses. In the middle of it usually is a citadel, a strong defensive core. Your website/app is like the castle, and WebARX is the citadel in the middle of it, keeping an eye on and providing security. WebARX is the defensive core of your web app.

Cloudways: Today, WebARX is used by thousands of customers. Please share your experience of building the product from scratch and what was the turning point for you being the CEO? 

Oliver: At first I was a single founder which meant that I had to be involved with each section of the company; support, marketing, development, R&D, finances, fundraising, and more. Becoming CEO at one point was a natural development of how things went. It’s been a long process and fortunately, we have had extremely experienced people help us on this journey. We have been building (and rebuilding) the WebARX core starting from 2016.

In July 2018 we reached a moment where we saw that it is ready for the public. It was a time when we did the product launch.

Cloudways: Cybersecurity is a sensitive domain and trust plays an integral part in expanding the client base. How did you deal with the criticism from the community in the early days?  

Oliver: Cybersecurity is sensitive and extremely conservative, and sometimes I find myself thinking that I probably found the most sophisticated industry to work in.

Trust is definitely important, as well as being honest and transparent. Even in marketing, we always try to communicate things as they are without dangerous marketing promises (such as 100% security, etc. that is unrealistic). I think the only way to cope with criticism is to improve the product and service and give proof of what we do, not what we say.

Cloudways: In your opinion what are the most common security vulnerabilities that cause cybersecurity incidents. What fixes you recommend for these issues?

Oliver: When talking about the most common security vulnerabilities for websites, that are based on CMS like WordPress, I would start off with poor password management (people reuse passwords that are also easily guessable).

Also poor development/maintenance practices (people don’t check what components/plugins they install and later on don’t keep them updated) and also saving money from places they shouldn’t (cheap hosting providers with questionable server architecture, lack of server-side backups, etc).

When it comes to general cybersecurity, I think it slightly overlaps with password management, software/system maintenance, but what I think is the biggest issue is security awareness. I mean social engineering attacks (such as phishing, etc.).

Cloudways: Being an expert, what five tips would you like to share with the people who want to start working in cybersecurity? 

Oliver: Stay curious and learn every day, try to think like an attacker, help others without asking anything back, find a mentor.

Cloudways: In your opinion what level of security a managed cloud hosting can offer when compared to unmanaged VPS or shared hosting?

Oliver: I think it’s about focus. Frameworks such as WordPress has its pros and cons that you should be aware of. If a hosting company is focused on some platforms and manages a portion of the service for you, much more could be done more effectively on the lower level.

There are decent shared hosting companies as well, but most are very cheap. I usually say to those who are looking for the cheapest options: you get what you pay for.

VPS will be exactly as good as you are. If you’re technical and know your way around all the technical bits, that’s probably the most secure way to go. It gives you the possibility to build an environment with elements that are only needed for your web app. If you’re not as technical, but want the freedom and benefits of VPS without having to configure everything yourself manually, managed cloud hosting is the best option.

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Cloudways: What resources/tutorials/blogs/ebooks do you recommend to cybersecurity enthusiasts (like myself :)) or a developer in general?  

Oliver: Hackbusters.com is a good aggregator of different cyber-sec sources, that can save time (new blog posts from Troy Hunt, Brian Krebs, etc. are all aggregated there). Podcasts, such as “Security Now” is a great thing to listen to. I’ve been also a fan of cybrary.it. If you’re a plugin developer, check out plugbounty.com

Cloudways: Finally, what tools do you use daily to streamline workflows and communication? 

Oliver: Slack, Gsuite.

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Ibad Ur Rehman

Ibad Ur Rehman is a WordPress Community Manager at Cloudways. He likes to explore the latest open-source technologies and to interact with different communities. In his free time, he likes to read, watch a series or fly his favorite Cessna 172SP in X Plane 11 flight simulator.

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