Interviews and Reviews

“Success is a Function of the Number of Attempts”: An Interview with Fractional CTO Illia Shkirenka

Fractional CTO Illia Shkirenka

Many large businesses started as startups, but coming up with an idea, launching it, and staying on course is extremely challenging. Often, teams lack technical and managerial skills, and hiring a CTO is beyond their limited resources. Illia Shkirenka, Fractional CTO and startup advisor, shared how his work helps startups and what new founders should focus on at each stage of their project’s development.

Illia Shkirenka is a CTO and a professional in technological entrepreneurship with expertise in advising startups. He is a mentor in several international business accelerators and the creator of his own startup evaluation approach.

Currently, Illia operates in a fractional format, meaning he works for companies in blocks or on a project basis rather than full-time. This allows him to have contracts with multiple companies simultaneously.

Tell us about your career path and how you came to the role of Fractional CTO.

My career began 14 years ago as a front-end developer at a small Minsk web studio, Jazz Pixels. Over time, I transitioned into back-end development as I grew professionally. I built a high level of trust with the company founders, demonstrated my skills, and in 8-9 years, I rose to the position of CTO.

Our company grew and, with my active involvement, it was acquired by the European digital corporation Mediapark, becoming its Minsk branch. I took on the role of Tech Lead and a company’s branch CTO there as well.

After about two years in this role, I decided to focus on what I truly enjoy — technical leadership and working with startups. I wasn’t ready to go full-time again but wanted to share my knowledge and gain new experiences. That’s how I discovered the benefits of the fractional format.

I started collaborating with various companies as a technical consultant, advisor, and Fractional CTO. Over the years, I’ve worked in various roles, from full-stack engineer to DevOps specialist, from solution architect to CTO. This combination of experience provides many advantages, as I can combine technical knowledge with product and startup expertise. It allows me to evaluate projects from different angles and make more balanced and effective decisions.

The role of an advisor and Fractional CTO brings me immense satisfaction and allows me to utilize the experience and competencies I’ve accumulated over 14 years. This format helps me gain rich expertise in various fields, broaden my horizons, and learn new things. I limit myself to two or three projects to stay focused and be as effective as possible.

What projects are you currently working on in this role, and what tasks do you address?

My work in projects is extremely varied: in some, I focus more on deep technical aspects, while in others, I optimize and set up processes. I have extensive experience in all segments of tech-related business, so I can apply my knowledge to almost any task. Currently, I’m involved in two projects, mainly addressing technical issues related to digital product development.

The first company is the Indonesian mental health startup, Tenang AI. It’s an AI assistant for psychological support, which also offers video sessions with psychotherapists. The project is still in the fundraising stage but has already received soft commitments from several funds thanks to its participation in a startup reality show. They are now developing a B2B platform to offer similar services to employees of various companies in the Indonesian market. Here, I act more as a technical advisor, helping shape the technical development vector.

My second project is the startup “vNorme”, a service for selecting psychotherapists and psychologists. In this, I play the role of Fractional CTO — directly sharing my technical expertise with the team. Initially, I worked on managing external contractors, but now I’m focusing on expanding the technical team and developing the product.

You seem to have your own experience in developing startups as a co-founder, correct?

Yes, over the past four years, I’ve been actively involved in developing my own startups, mainly as a technical founder. This has given me substantial experience in building products from scratch — both technically and from a product perspective. It’s not enough to know how to do something; you also need to understand what to do and why. Combining technical expertise with product knowledge allows one to make crucial decisions that increase the product’s value for users.

Among the most significant startups, I would highlight Platto, which I’m currently working on. It’s a digital QR menu for restaurants, cafes, and hotels which incorporates ordering and online payment features. We are testing various markets and examining unit economics to continue its development.

I can also mention MixMatch — a service for conducting networking sessions in business communities. The product is still in development and is used by various business communities for networking sessions.

Being an entrepreneur and founder is genuinely exciting because it helps one develop an entrepreneurial mindset over time. I love the phrase, “Success is a function of the number of attempts”, because it encapsulates a mindset which involves learning from mistakes, testing hypotheses, studying, and experimenting. It’s more challenging than working in a job, and there’s no stability or certainty, but I see it as a game.

The main thing in entrepreneurship is to have a vision for the product you are constantly working on and making better and clearer. But, of course, such a life is not for everyone — some need predictability, stability, and psychological peace.

In entrepreneurship, I see a vast horizon for self-realization compared to employment. It also helps me in working with startups as a Fractional CTO. When I interact with startup clients, I bring in business experience, while my technical knowledge allows me to stay on the same page with the team.

Additionally, entrepreneurial experience helps me contribute through working with startups in various accelerators and VCs. For example, I mentor in international accelerators like Founder Institute Startup Accelerator and UltraVC. I’ve even developed my own approach to evaluating startups, which I hope will contribute to the development of technological entrepreneurship.

What do you see as the main advantages of the Fractional CTO model for startups and small companies?

Often, startups begin by collaborating with an external vendor to create an MVP. After successfully launching the MVP, they want to continue developing independently, but many lack the expertise to build technical processes. In large companies, this is handled by a CTO or Tech Lead, but startups often don’t have the resources to hire strong engineers or a CTO, and finding such specialists quickly is challenging. This is where a Fractional CTO can help.

A Fractional CTO provides the necessary technical expertise and sets up processes for the company to grow. When the startup’s revenue increases, the team can hire a full-time CTO or continue using the services of a fractional specialist.

Additionally, a Fractional CTO typically has more extensive expertise as they work with multiple projects simultaneously. Thus, they can support an in-house CTO, for example, in the field of AI.

Prioritizing can be challenging when working on multiple projects even within one company. How do you effectively manage this while working with multiple clients simultaneously?

I use various time management techniques to help me. I also try to allocate consistent blocks of time for each startup. For example, I might work with one client for two consecutive days and the remaining three days with another. This way, I don’t switch between clients.

If a task is complex, I might work with a client for several weeks in a row, such as when building an MVP or implementing a feature in a product. In such cases, my activity closely resembles project work in a large company. When I need to take calls for another project or handle cross-project tasks, tools like a management calendar, Eisenhower matrix, and to-do lists help.

I also strive to maintain a personal life that brings me joy.

We see that the level of technology is constantly rising, and understanding it without specialized knowledge is quite challenging. What would you advise non-technical startup founders for effective work in high-tech business segments?

It all depends on the task the founder wants to solve, the startup’s business model, and the problem it addresses. For example, an MVP can be made using no-code solutions and relatively simple technologies — in 90% of cases, deep technical expertise isn’t required.

If the hypothesis is validated and the product proves viable, it makes sense to develop it further into a standalone business. At this stage, you can bring in team members, seek technical advisors, or hire a CTO. They can help build a complex technical product, for instance, using large language models (LLMs).

You mentioned helping startups as an advisor and mentor. What are the main challenges faced by the startups you work with?

Challenges also depend on the startup’s development stage. In the early stages, they often struggle with product development and hypothesis validation. Here, technical assistance is crucial to understand how to build an MVP using current tools or no-code solutions. One of the main tasks I work on in startups is helping create the MVP, establishing technical and business processes, and finding Product-Market Fit.

As a startup advisor and mentor, I audit the idea: whether the customer development (custdev) was conducted properly, if the startup understands the problem it’s solving, and if it has chosen the right solution format, among other things.

When the startup proves the idea’s viability, the challenge is to turn the current MVP into an independent business. At this point, other tasks come to the forefront: establishing a release cycle according to industry standards, setting up continuous integration and deployment of code, optimizing team processes, implementing a working methodology, and so on.

At later stages, startups usually need to implement new features that must be integrated into a larger, already functioning system without breaking anything.

I also help startups at any stage with fundraising — supporting founders in communicating with venture capital funds (VCs) and helping form a technical strategy.

When working with founders, I strive to build highly empathetic communication. Any startup consumes a lot of energy, and it’s essential to have the strength to move forward. A mentor’s task is not only to provide technical or business development assistance but also to inspire and support the team.

Frequent mistakes and failures can demotivate founders, making them want to return to familiar employment, where everything is clear and stable. Therefore, I build the right mindset for startups — teaching them to work with uncertainty, not fear mistakes, and keep moving forward. It’s important to remember that with each new iteration things will get better and better.

So, my advice to all founders is to pursue their goals, stay on course, and believe in success. And, of course, seek help from advisors and mentors — it makes navigating all stages of startup development much easier.

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