C-suite career advice: Dob Todorov, HeleCloud

Did you always want to work in IT? "I was 9 when I started developing my first programmes in Applesoft Basic on a community centre Apple II. I was hooked pretty much from day one..."


Name: Dob Todorov

Company: HeleCloud

Job Title: CEO

Location: Maidenhead, UK

Dob Todorov is HeleCloud’s Co-Founder and CEO, having founded the company in 2016. Prior to founding HeleCloud, a specialist AWS Cloud solutions provider, Todorov spent 5 years working for AWS as its Regional Technology Officer in EMEA.

What was the most valuable piece of career advice that you received? I wish I could say I’ve been given a piece of business advice from a wise and knowledgeable leader that made me rethink my career and put it in order. Alas, I’ve not had that, but I have had profound revelations in otherwise casual conversations with friends and colleagues. One of those revelations still stands out today, 15 years after I first encountered it: “Life doesn’t ask us what we want; life gives us options. It is up to you to select which option you want to take, but it’s a limited set of options and neither of them is likely to be exactly what you want.” It was a very simple yet very clear and impactful piece of advice that I still remember, and I keep passing it on today. It’s up to us to maximise the options; it’s up to us to choose one – albeit not exactly what we want, or could be – very different from what we want. It’s all in one’s control but you need to understand the principle of options, and not the notion of “what I really want”.

What was the worst piece of business advice that you received? “You should do your maths before launching this business and put everything in a business plan.” I know that it is counter-intuitive and that responsible and intelligent people make rational decisions and plan everything, so the advice was well-intended. However, life and business are largely irrational – you can’t always foresee the predicaments your business may face and often you are building business plans based on hopes and dreams. Most good ideas or businesses come from a leader following their passion who is unburdened by prejudice, negative experiences or old school industry thoughts. 

What advice would you give to someone starting their career in IT? It’s a 24x7 job: whether you are learning new technologies, thinking about solutions, responding to urgent requests, implementing new systems in out of business hours, selling, leading projects or companies… For a successful career in IT, you need to be prepared to go all in. In other industries, perhaps you can still be very dedicated but get away with less. In the fast-changing world of IT, you must be ready to give it your all.

Did you always want to work in IT? I was 9 when I started developing my first programmes in Applesoft Basic on a community centre Apple II. I was hooked pretty much from day one, and never looked at any other trade. I am only realising this now, faced head on with the question, but I’ve never considered another walk of life. 

What was your first job in IT? In the early 90s, I had my first job as a systems administrator for the local survey and mapping department in a small town in central Bulgaria. I was expected to be the most knowledgeable among the team when it came to the small IT estate of roughly 10 computers and printers as well as a small local area network. The rest of the team consisted of non-IT people, so it wasn’t a huge challenge even though I had just graduated from secondary school. It wasn’t a demanding or glamorous job but one that gave me precious time and early experience to ponder what I wanted to do for the rest of my life – it certainly made me realise I wanted a more challenging role.  I think everyone needs stepping stones on their journey up their desired career path, and each of these stones, however small, builds the stairs that we climb to get to the next level.

What are some common misconceptions about working in IT? Perhaps it’s that IT geeks are boring, know everything, and hack in every system in seconds: that’s the stereotype that I see in most films and TV programmes. My experience with IT geeks – myself included – is that you’ll find all kinds of people in IT, not unlike any other walk of life. What is common across all the real nerds out there in IT is that they have a very romantic relationship with technology; it’s not dry or boring at all: people geek out for the love of what they do, whether it’s writing code, architecting applications and systems, configuring infrastructure, designing test cases. I know many knowledgeable IT professionals but none of them know everything and even fewer are hackers in the way that films and TV shows suggest. 

What tips would you give to someone aiming for a c-level position? Not all C-level positions are the same – they differ across industries/verticals and horizontals. However, it’s fair to say that in most medium to large organisations, C-level positions require more leadership skills and experience and far less technology skills and experience. That being said, IT professionals that possess deep technical knowledge can be outstanding leaders but more often than not, C-level executives follow a different career path away from IT engineering, service management, enterprise architecture or branch out from IT engineering relatively early in their careers. 

The transformation from technical knowledge and skills to leadership knowledge and skills for a C-level position can be a shock to many. Technical roles mostly require cognitive intelligence and skills, exact and timely information, fully predictable environments and systems, and communication to exchange information. At C-Suite level, one has to focus on emotional intelligence much more than on cognitive intelligence, to be able to work with ambiguity and make decisions based on partially available information, to deal with uncertainty and probability, to communicate to build relationships (and often – not to exchange any useful information). Unlike all the individual contributors in a company – whether technical or business – as the leader of leaders, the C-Suite need to work on the organisation: it is their role to establish the right organisation, to hire, develop, manage and govern the business. 

It’s important for those aiming for C-level positions, especially if they are coming from an individual contributor background, to realise the C-level role in the above context. And if that’s what they really want to do, they should go ahead full steam. But one really needs to accept these predicaments of the C-level roles – they come with the title.

What are your career ambitions and have you reached them yet? I need to know that what I am doing has an impact on people’s lives and hopefully one day on science and the future of IT. Whether knee-deep in technology or with my business head in the clouds (pun intended), I’ve always felt like I am making an impact on people, on society and on the industry – but I’ve got a lot more to do. 

My immediate ambitions are that HeleCloud continues to lead the Cloud revolution and help our customers across all verticals and horizontals to make the most of Cloud. We want to continue to provide the knowledge and experience to help our customers thrive and succeed in their markets as they embark on their cloud journey. 

Do you have a good work life balance in your current role? One must find such a balance. Left to my own devices, I can work very long hours. However, doing so for long periods is exhausting and reduces productivity - it may lead to suboptimal or plain wrong decisions. It can also harm the technical or business outcomes that one is expected to deliver. 

Especially when a business leader overworks, such suboptimal decisions may have a much more significant blast radius. Thus, even the workaholics among us need to be able to restrain ourselves and find such balance. I love spending time with my family, reading, and doing sports, so I always find time to detach from work and indulge in other passions and activities.

What, if anything, would you change about the route your career path has taken? In hindsight, I have made many mistakes and naturally would be inclined to avoid them if given a chance to go back in time. At the same time, mistakes present the best opportunities to learn and develop new skills, invent, experiment, improve and grow. If I had avoided my previous mistakes, would I still have the knowledge and experience that I have today? Would I still be where I am today? I’d rather cherish all the successes and mistakes as they make us who we are. 

Which would you recommend: A coding bootcamp or a computer science degree? I don’t think that an academic degree is necessary to excel in IT. Over the years, I’ve had many colleagues, friends and acquaintances that didn’t have IT degrees yet were excellent professionals in their field. Likewise, I’ve had colleagues who sadly had such degrees but were not interested and naturally did not excel in IT as their hearts were elsewhere. The key ingredient is passion for IT; the knowledge and experience follow this passion and one can find different ways of acquiring them – whether a computer degree or one or more courses, such as coding bootcamps.

Computer degrees though are important for two considerations: first, because they provide one with a holistic view of IT, thus broaden one’s horizons and perhaps allow them to also uncover other passions; the second consideration is the time, effort and perseverance it takes to go through all the courses required to graduate and acquire the degree – it shows (and teaches) character. It is for these reasons that I would generally recommend a computer science degree. The drawback is that at least in my experience, computer science courses inevitably lag behind the latest developments in the field, and often only teach foundation knowledge, mostly detached from the latest trends. Thus, computer science graduates still require a large amount of self-study or coding bootcamps to catch up with the more pragmatic side of real IT life. That’s why some simply skip the academic years and go for the bootcamps, and if your career goal is to be a great coder, that may well be the best way to achieve this goal.  

How important are specific certifications? Certifications don’t provide knowledge or experience but are proof of knowledge and experience. Some people find it important (and sometimes – necessary) to provide such proof to the wider world; others find it important to prove to themselves that they can acquire the certifications. In these two cases, I’d say they are very important. We at HeleCloud require all of our consultants and engineers to maintain certain AWS and wider industry certifications for both of these reasons. It helps us establish and maintain high standards across the entire technology organisation. We’ve also imposed similar, less technical certification standards to different functions within the business. So to us as a knowledge and services business, certifications are very important. We don’t expect that new hires will be certified; but we make it clear that once onboard, they must go through the process.

What are the three skills or abilities you look for in prospective candidates?  Hiring top talent is the highest priority for HeleCloud, much more than financial performance. People are at the core of everything that we do as a knowledge and services business, so if we hire, develop, and empower top talent to deliver results, everything else follows. We are very particular about attitude (and will always hire for attitude over skills or experience), cultural fit (we want to be the right company, where people feel they belong, and that they are valued, challenged, and responsible for the results that they deliver), and assuming that these are in place – we’ll go for deep technical or business knowledge.

What would put you off a candidate? We are specific about cultural fit at HeleCloud; we have four main pillars to our culture – We Deliver, We Belong, We Lead and We Learn. It’s not a matter of a specific character trait putting me off – cultural fit is more important than my personal preferences or opinion here. If a candidate doesn’t see themselves as belonging to the team, delivering results rather than just geeking out, daring to lead beyond the everyday existence, and being able to constantly learn, aggregate, synthesise and share knowledge – this candidate is unlikely to be successful at HeleCloud, and we’d honestly and respectfully let them know that they would do better elsewhere.

What are the most common mistakes made by candidates in an interview? How can those mistakes be avoided? We tend to help candidates settle and predispose them for the interview. We don’t expect candidates to be very experienced in the interview process, or to have gone through many interviews, so it’s important to set them up to showcase their merits. If we can, we want to see the real candidates – their cognitive and emotional intelligence, their experience, their passions, and not just a façade. The biggest mistake is to hire a candidate that then doesn’t feel comfortable in the role or the company as a whole – and that’s a mistake made by a company, less so by a candidate. Candidates pretending to be someone they are not, of course, make such mistakes more likely. 

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