STORY Career & Transitions Growth

I Suddenly Became a CTO: Cold Decisions Atop a Collapsing System

From Executive Director of Strategy to CTO—A record of leadership proven through restructuring and technical redesign.

Vailyn
Vailyn 2026.04.18
I Suddenly Became a CTO: Cold Decisions Atop a Collapsing System

An Unplanned Title: Stepping onto a Stage I Didn't Choose

Life often changes course through absurd coincidences rather than meticulous strategy. When I first joined that startup, my title was "Executive Director of Strategy and Planning." My mission was to use my consulting background to paint the big picture of the business and set up the organization. At that time, the only team under my management was the design team.

However, the situation shifted drastically mid-project when the CTO suddenly left the company. It was like the ship had already set sail, but the captain had vanished. I had no choice. One day, I found myself standing in the position of Chief Technology Officer (CTO), overseeing everything from Frontend and Backend to the AI team. There was no time to prepare and no room to refuse. The moment the title was granted, the role began mercilessly.

The Weight of Proving Myself While Still Learning

The position of CTO is a place where the excuse "I don't know" does not work. At the time, I didn't fully understand the granular logic of the entire development stack. To make matters worse, the team members were all fresh graduates at their first jobs. An inexperienced junior team led by a leader who (seemingly) didn't know the technology—the external gaze, especially from investors, was cold. They didn't trust me at all, viewing my title as a mere temporary fix.

What made the problem even more complex was the system itself. It wasn't just a matter of simple bugs; the fundamental technical architecture was a mess, and there was a deep divide between planning and development. Amidst the daily fires, I had to decide: run away, or make this system my own? Since "giving up" was never in my vocabulary, I chose a head-on breakthrough.

Gaining Trust Through Late Nights and Architecture Redesign

The only way to gain the trust of investors was through "results," not "words." In the silent office after everyone had left, I began staying up all night. Even if I couldn't write every line of code myself, I had to perfectly grasp the overall system architecture and the flow of logic. I redrew the technical blueprints and transplanted my strategic thinking as a planner into the technical design, identifying the root causes of the system’s failures one by one.

I didn't just propose fixing a single feature; I stood before the investors with a proposal that corrected the fundamental design and realigned the planning. When I presented an analysis and alternatives that pierced the essence of the problem, their eyes began to change. The fatigue of the past weeks washed away the moment I was recognized with the thought: "This person understands the core of technology and knows how to solve problems." It was the moment strategic leadership translated into technical credibility.

Reorganizing a Broken Team and Making Bitter Decisions

Leading a team of fresh graduates was a test of the limits of my leadership. When I joined, the team’s cohesion had already collapsed, compounded by funding issues and a lack of core competencies among the staff. In such a chaotic situation, I couldn't afford to be a "nice leader" who tried to carry everyone. To protect the survival of the company and the trust of our investors—who were also our partners and clients—I had to make cold, calculated judgments.

Ultimately, I proceeded with a painful but necessary restructuring. In that process, I identified and retained only one core backend developer to reorganize the team. Working closely with him, we began to fill the gaps in the system and respond to the demands of our client-partners with tangible results. These bitter decisions made amidst personnel issues and financial pressure taught me the harsh reality of entrepreneurship and the profound impact a leader's decision has on an organization's survival.

How a Talent Vacuum Created a "Real Builder"

As time went on, the company's circumstances led to more staff departures. With the management system loosening as team members left, I began to get my hands dirty with the code and designs I had previously only observed. I started with simple modifications. Having kept the system's blueprints in my head as CTO, finding my way through unfamiliar code was easier than I expected.

This brief but intense experience of directly modifying code and studying design taught me a great lesson. It was the sensation of my head as a strategist and my hands as a builder finally connecting as one. Although that startup eventually dissolved, the "weight" I felt while tapping on the keyboard back then has become the strongest engine driving me as I build my own services today.

Roles Change People; Experience Creates Standards

I started in an unprepared state, but that role completely transformed who I am. I no longer believe that I must know everything perfectly before I can make a decision. I've learned how to identify priorities, manage risks, and make calls even when I'm still learning the ropes.

The experience of agonizing over technical designs late at night, responding to the sharp questions of investors, and those final moments spent alone touching the code have accumulated to make me who I am today. I now look at things more structurally and move with a much more defined set of standards.

Conclusion: Cheering for Every Sudden Start

Are you suddenly facing a role that feels too heavy to handle? You might want to run away due to the anxiety of being unprepared. But remember: responsibility pulls a person up to unexpected heights. I was able to transform from a strategist to a CTO, and now into a solo builder, because I didn't avoid that "sudden start."

It's okay to be imperfect. The desperation you feel while trying to solve a problem and the attitude you show to maintain trust will eventually become your strength. I hope this rough and fierce record of mine provides a small measure of courage to all the builders facing unexpected challenges.

"Please support my growth story of forging my own path while fulfilling responsibilities atop a broken system.
Your support is a great source of strength for me to become a more resilient builder and share more valuable experiences with the world."

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