What You Need to Know before You Start as CTO

I started out as a frontend developer and went through all standard stages: from a junior to a senior and a team lead and, later, to the head of a department. The next logical step was, of course, a CTO. And it was only several years later that I learned that my ideas about this role had been far from reality. This article is about how I became CTO at a large-scale company and learned the rules of the game by experience. If you are interested in what this job is about or planning on taking on this position, welcome on board! Who I Am Everything I’m going to share is my personal experience hard won during 17 years of work in tech. In a nutshell, it was like this. In my youth, I was your typical geeky loner who then graduated from one of the top Russian technical universities and could imagine himself only as a tech guy. When I got my first job, I felt that I was good at noticing the mistakes of my superiors and decided that I could do it right if I were in their position. That’s why I moved forward at a very fast pace and got four promotions in five years. The next highest position in my company was CTO. And that’s what I aimed for: the title sounds good and offers lots of opportunities to do things right. But the company didn’t need a new CTO at the time. I was young, eager and rushed forward, so my friends and I decided to launch a startup. For the next eight years, I was an entrepreneur, founding and selling, founding and selling companies. In all these cases, I essentially assumed the position of Head of Engineering. Then came 2019 when I realized that I was ready for employment. Just like that, I became CTO of a large-scale e-commerce company, Citilink. Next year, in 2020, I got an offer that I couldn’t refuse from Lamoda. In fact, my path as CTO started a lot earlier but it’s been official for the last four years only. And it seems that I was doing some other stuff between the time when I first dreamt about it and the actual work as CTO. This journey has brought me to a position where I could draw a comparison between my dream and reality. The results shocked me at first, then I hated them, but finally came the acceptance. Now it’s time to share them. Partnership As they say, first impressions count. In my case, it was an absolute surprise because I was interviewed by CEO who was by no means a tech guy. No directors with whom I communicated were tech-savvy. They were looking for CTO who would be smarter than them and would deal with all technical matters. They themselves were exceptionally talented business managers, driving the growth of their companies. But they had nothing to do with technology. And what were they talking about during the interviews? Each of them did it the same way: their main objective was to find a person who would help them grow their business. Both times (in Citilink and Lamoda) we talked about what I had done for business growth. If I worked for a company, then what was its business objective at the time? What were the shareholder’s purposes, what did CEO want, and did I achieve what they wanted? If so, then how? Why this way and not another one? It was important for them that I understood CEO’s and business objectives and contributed to their achievement. So, this was the first lesson I learnt from the first interview: If you want to be CTO you need to become a business partner, the person who helps CEOs grow businesses and achieve their objectives, namely growth, be it turnover, capitalization, profits, customer base, and so on. It was important not only for passing the interviews: it also helps work and build trust with CEO and your colleagues. If you want the business to grow the same way your colleagues do, you will belong and be trusted. Even more, you will be allocated the resources you need and your opinion will matter in any conflict situation. If you close up and become defensive (as in “we are IT, and nobody from the outside can understand us”) you will lose. Sooner or later, the conflict will become evident, cracks will open, sparks will fly, and somebody will get fired. Communications Imagine: you are entering a room with nine people who know almost nothing about technology. You have been working in tech for 17 years, and they haven’t written a line of code in their lives. But they are smart and influential people, they make decisions about your budget and whether you can complete your project or introduce new technologies. In the end, they decide on corporate policies: for example, whether to allow your developers to work remotely or not. These people are your management board, a managerial body CTO is part of. Now imagine that you need to explain to these people that your monolith platform requires refactoring. It will cost 60% of the company’s budget for growth and will last 1.5 years (or maybe even two), and if you don’t do this, the company will suffer. You need to explain this to people who know nothing about technology and even if they do, their knowledge is very limited. This case is your typical working day as a CTO. You work with these people on a daily basis, and they decide on many steps you take. You need to be convincing and clear so that they wanted to agree with you even if they don’t have your 17 years in the industry. Once, I had to keep my ground against the Board of Directors (which is the next level of the management, the company’s shareholders) to persuade them to spend two million dollars on a new data storage system. This turned out to be one of the most difficult communication situations in my whole life. Behind me was my team, who needed appropriate equipment to do their work, and before me was a shareholder who could hear only: “Give me two million” from my speech about the issues with queues and the importance of the upgrade. And this isn’t so surprising: after all, it’s his personal income that he already decided to spend on a new yacht. I was able to solve this problem and, to be honest, I am proud of myself. Here is the magic: a shareholder doesn’t like to spend but he likes to earn. In his experience, it is the Business Development Manager or the Marketing Director who earns money, while the Head of Engineering just spends all the time: and the shareholder already dealt with dozens of tech guys who kept asking for money! Turns out you can actually pique a shareholder’s interest, but only if you discuss potential extra income with him. That’s why my first approach failed: I kept telling him about the spending and couldn’t understand why he couldn’t recognize the seriousness of the problem. In the end, I turned my request into an investment package: you give us X money now, and we return 3X in three years. We calculated the increases in the page load rate and SEO traffic, as well as in the conversion rates during the holidays when the demand is the highest. We also ensured that the issue with order delivery would be solved (because all order tracking systems were installed on these machines and, at peak loads, pickup points received order information only several hours later). Only business people usually promise a return on investments and we, tech guys, partnered up with them. Being a reasonable person, the shareholder agreed: because three yachts are way better than one. That’s how we got much more than two million for our new software. So, that’s what CTO’s daily life looks like. You communicate with people who are very smart but don’t know anything about technology and don’t even want to talk about them. Because it's your job to know all about the technologies. And you need to do whatever it takes to reach understanding. Strategic vision The third pain point catches up on you later, and it is not so obvious. You work and make some decisions every week. They can be quick fixes or long-term solutions: what architecture to choose, whether to split a monolith, to migrate from a data center to a cloud solution or vice versa, to which degree to use import phase-out, what to buy and what to develop internally. Nobody can answer these questions better than you. Just remember that it is important to be a business partner and to earn trust. And the easiest way to earn trust is to focus on quick wins when you do your best to resolve immediate and urgent problems. For example, quickly release a feature much expected by the stakeholders. And it doesn’t matter at all that you achieved it with crutches and overtimes. And it’s important because it creates trust, with you demonstrating the spirit of business partnership. Problems start to arise when you realize that, for these quick wins, you will have to sacrifice the long-term future of the company. Your team can work overtime and your feature will be released by Monday. But if you do it too often, people will burn out and leave, causing a drop in the number of tasks you can complete. You can release your feature with crutches. But if you do it every week, you will end up with an architectural cul-de-sac instead of a solid architectural environment. You can outsource all the work and, in doing so, avoid difficult problems because you won’t need to compete for talents. But then, in all likelihood, you will be less flexible long term as you won’t have the required competencies. And at some point, when the company needs motivated employees, it will turn out that you don’t have them because you either use out-of-the-box solutions or external teams who are not that much attached to you. You always have to keep a balance between short-term and long-term approaches. You have to demonstrate short-term results: any homo sapiens likes to win, and any manager or colleague likes it when you demonstrate results. If you don’t, you lose the benefit of the doubt. And when you lose it completely, your place will be taken by another CTO with his own strategies. When I was looking for a job, I had a heart-to-heart with an executive search agent. She told me that some of my fellow colleagues are considered bad candidates because they were after short-term benefits and “spoiled the IT landscape”. That’s because they felt pressured into it by the business owners and wanted to be their business partners. This article starts with an emphasis on the importance of business partnership, and here is the paradox: you just can’t solve the quick/long wins issue. This is the burden you will have to carry. This is the work you will have to do. This is the conflict that will persist in you. What is the way out? I’ve been working as a CTO for almost four years and have been searching for an answer to this question all this time. Right now, I am confident about one thing only: you need to have a clear strategic vision. Then, you will have an understanding of where a long-term initiative is crucial and when the company will not succeed without it. Here is an example. We, at Lamoda, believe that a high-caliber team with senior specialists guarantees the health of the organization and its technological sustainability. Sometimes, I feel tempted to take a different road to speed up right here, right now. But then I always remember that expertise is the guarantee of stability for us. To tell you this now or, more importantly, to communicate this message to the CEO when he approaches you with a bundle of ideas (“Let’s do it this way? Why not?”), . You need to have , and the will to stand your ground. you need to have inner conviction vision faith At the same time, you need to be . Defend only what is the most important. And don’t go for quick wins when losses are negligible. wise Do you really want it? My story may look like a path of wins but it’s not by accident that I’m being so dramatic about this: each of these thoughts is a result of hundreds of failures. Up to the point when I was told: “You are a lousy CTO. I advised to fire you.” It hurts. And if you choose this road you will most probably be hurt, too. The experience in software development doesn’t prepare you for the problems awaiting you: you will need to hone your communication skills and become well-versed in business matters and strategies. You will have to spend time on this, while you could spend it upgrading your technical skills. And the question is: does a geek, a graduate from a technical university, or a fan of coding, really need this? Maybe, you will be happier and more successful professionally if you choose a level lower or sideways from this position. I have asked myself this question multiple times. But I always had the thought that kept me going from the very start: “I want everything to be better and cooler after me than it was before me. I want the developers at my company to not have the issues I had. I want to work in the industry that changes for the better every day. I don’t want to give up.” That’s the answer to my question, that’s my motivation. However, payback is inevitable. If you want to do something better than the previous dumb superior, you will sooner or later realize that now the dumb superior is you. But that’s another story. Maybe, I will tell it later.