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

Illia Shkirenka is a CTO and a professional in the field of technology entrepreneurship, specializing in consulting startups. He is a mentor in several international business accelerators and the creator of his own approach to evaluating startups.

Illia currently works in a fractional format, meaning he works for companies in blocks or on a project basis rather than on a full-time basis. This allows him to contract with multiple companies at once.

Tell us about your career path and how you came to be Fractional CTO.

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

Our company grew and thanks to my active involvement it was acquired by the European digital corporation Mediapark, becoming its branch in Minsk. I also took on the role of Tech Lead and CTO of the company branch there.

After about two years in that role, I decided to focus on what I really enjoyed—technical leadership and working with startups. I wasn’t ready to go back to full-time work, but I wanted to share knowledge and learn new things. That’s how I discovered the benefits of fractional format.

I started working with different companies as a technical consultant, advisor and part-time CTO. Over the years, I worked in different positions, from full-stack engineer to DevOps specialist, from solution architect to CTO. This combination of experience is very beneficial, as I can combine technical knowledge with product and startup experience. It allows me to evaluate projects from different perspectives and make more balanced and effective decisions.

The role of advisor and fractional CTO brings me great satisfaction and allows me to use the experience and competences I have accumulated over 14 years. This format helps me gain a wealth of experience in different areas, 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 position and what tasks do you perform?

My work in projects is extremely diverse: in some I focus more on deep technical aspects, while in others I optimize and configure processes. I have a lot of experience in all segments of the technology business, so I can apply my knowledge to almost any task. I am currently involved in two projects, mainly dealing with technical issues related to the development of digital products.

The first company is an Indonesian mental health startup, Tenang AI. It is an AI assistant for psychological support that 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 currently developing a B2B platform to offer similar services to employees of different companies in the Indonesian market. Here, I act more as a technical advisor, helping to shape the technical development vector.

My second project is a startup called “vNorme”, a selection service for psychotherapists and psychologists. I am the Fractional CTO there, sharing my technical knowledge directly with the team. Initially, I worked on managing external contractors, but now I focus on expanding the technical team and developing the product.

It sounds like you have some experience growing startups as a co-founder, right?

Yes, I have been actively involved in growing my own startups for the past four years, primarily as a technical founder. This has given me a lot of experience building products from the ground up — both from a technical and product perspective. It’s not enough to know how to do something; you also need to understand what to do and why. Combining technical knowledge with product knowledge allows you to make critical decisions that increase the value of your product to users.

Among the most important startups I would highlight Platto, which I am currently working on. It is a digital QR menu for restaurants, cafes and hotels, which includes online ordering and payment features. We are testing different markets and studying the unit economics to continue developing it.

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 really exciting because it helps you develop an entrepreneurial mindset over time. I love the phrase “Success is a function of the number of attempts” because it captures a mindset that involves learning from failure, testing hypotheses, studying, and experimenting. It’s harder than a full-time job and there’s no stability or certainty, but I treat it like a game.

The most important thing in entrepreneurship is having a vision of a product that you are constantly working on and constantly improving and perfecting. But of course, that life is not for everyone — some people need predictability, stability, and peace of mind.

I see a broader horizon of self-fulfillment in entrepreneurship compared to employment. It also helps me when working with startups as a fractional CTO. When I interact with startup clients, I bring business experience, and my technical knowledge allows me to stay on the same page with the team.

In addition, my entrepreneurial experience helps me contribute by working with startups in various accelerators and VCs. For example, I am a mentor in international accelerators such as Founder Institute Startup Accelerator and UltraVC. I have even developed my own approach to evaluating startups, which I hope will contribute to the development of technology entrepreneurship.

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

Startups often start by working with an external vendor to build an MVP. After a successful MVP launch, they want to continue development independently, but many of them lack experience building technical processes. In large companies, this is handled by the CTO or Tech Lead, but startups often don’t have the resources to hire strong engineers or CTOs, and finding them quickly is a challenge. This is where a part-time CTO can help.

A part-time CTO provides the necessary technical expertise and processes to help the company grow. As the startup’s revenue grows, the team can hire a full-time CTO or continue to use the specialist on a part-time basis.

In addition, Fractional CTOs typically have more experience because they work on multiple projects at the same time. This allows them to support the internal CTO, for example in AI.

Prioritization can be difficult when you’re working on multiple projects, even within the same company. How do you effectively manage this when working with multiple clients at the same time?

I use a variety of time management techniques that help me. I also try to allocate fixed blocks of time for each startup. For example, I might work on one client for two consecutive days and another for the other three days. That way, I don’t switch between clients.

If the 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 these cases, my activity closely resembles working on a project at a large company. When I have to take calls on another project or handle cross-project tasks, tools like the management calendar, the Eisenhower matrix, and to-do lists come in handy.

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

We see that the level of technology is constantly growing, and it is quite difficult to understand it without specialist knowledge. What advice would you give to non-technical startup founders so that they can work effectively 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 solves. For example, an MVP can be created using no-code solutions and relatively simple technologies — in 90% of cases, deep technical knowledge is not required.

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

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

The challenges also depend on the stage of the startup’s development. In the early stages, they often struggle with product development and hypothesis validation. Here, technical support is key to understanding how to build an MVP using current tools or no-code solutions. One of the main tasks I work on in startups is helping to build MVPs, establish technical and business processes, and find product-market fit.

As an advisor and mentor to startups, I audit the idea: whether customer development (custdev) was done correctly, whether the startup understands the problem it is solving, and whether it has chosen the right solution format.

Once a startup has proven the viability of an idea, the challenge is to turn the current MVP into a standalone business. At this point, other tasks come to the fore: setting a release cycle according to industry standards, setting up continuous integration and code deployment, optimizing team processes, implementing a working methodology, and so on.

In the later stages, startups typically need to implement new features that need to be integrated into a larger, existing system without causing any breakage.

I also help startups at every stage of fundraising – I support founders in communicating with venture capital (VC) funds and help create a technical strategy.

When working with founders, I try to build highly empathetic communication. Every startup takes a lot of energy and it is important to have the strength to move forward. The mentor’s job 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 a familiar job where everything is clear and stable. That’s why I build the right mindset for startups — teaching them to work with uncertainty, not to be afraid of mistakes, and to keep moving forward. It’s important to remember that with each new iteration, things will get better.

That’s why I advise all founders to pursue their goals, stay the course, and believe in success. And of course, seek help from advisors and mentors — it makes navigating through all stages of startup development much easier.