On this episode, we have Maki Villano, Ragde Falcis, Rafi, and Andresito joining us to discuss the CTO Time Machine and how leadership evolves in a growing tech company.

The role of a CTO doesn’t stay the same for long. In a growing company, leadership evolves alongside the technology. This episode takes a time-machine-style look at how CTOs transition from scrappy early builders to strategic leaders managing scale, people, and long-term vision. Our guests share key lessons from both phases—and the moments that forced them to rethink everything they thought they knew about leading in tech.

What were your main responsibilities in your first year as CTO, and how have they changed? (Generalization)

In the first year as CTO, responsibilities were often hands-on and tactical. The primary focus was on building the initial product, making key architectural decisions, and writing a significant amount of code. The job was about being the lead builder and problem-solver. Today, the role has shifted to being more strategic and managerial. The focus is now on scaling the engineering organization, mentoring team leads, fostering a strong technical culture, and aligning technology investments with the long-term business vision.

How do you balance hands-on coding with long-term strategy? (Generalization)

Balancing hands-on work with long-term strategy is a constant challenge. The key is to delegate effectively and trust the team to handle the day-to-day technical challenges. While it's important to stay technically sharp, a CTO's primary value is in setting the strategic direction. This often means reserving a small portion of time for code reviews or small technical spikes, but dedicating the majority of time to roadmap planning, architectural governance, and identifying future technological opportunities and risks. It's about being a guide, not just a doer.

What’s something you wish you invested in earlier—tools, people, or processes? (Generalization)

Most CTOs wish they invested in people and processes earlier, as these are the true foundations for scaling. While a focus on building a product is natural at the start, underinvesting in hiring the right talent and establishing clear development processes can create significant bottlenecks later. This includes investing in strong talent acquisition, onboarding procedures, and implementing disciplined project management and documentation practices. Tools are important, but the right people and processes make the tools truly effective.

What does “success” look like now compared to when you started? (Generalization)

When starting out, "success" was often defined by shipping a product, fixing a critical bug, or hitting a technical milestone. It was a very binary, tangible form of success. Today, success is much more nuanced. It’s measured by the growth and autonomy of the team, the robustness of the system, and the ability of the technology to enable new business opportunities. Success now means building an organization that can innovate and scale independently, rather than just a product that works.