CTO Chats with Zayd Tolentino, CTO Stratpoint Technologies

Could you share a bit about your personal journey and how you first got into the IT field?

Honestly, I didn’t know what course to take after high school. On enrolment day, I looked at my report card, saw that my highest grade was in computer subjects, and just went with it. I never dreamed of being a developer, but I developed a passion for programming in my first year of university. I was ambitious—for my first project, I built an entire banking system in C.

After graduating, I realised I wanted to be someone who builds things, not just one part of a system. I was lucky enough to become one of the first cloud engineers in the Philippines around 2012-2013. This jump-started my career, as it allowed me to get into innovation and focus on building again.

What are some of the most significant challenges you’ve faced in your career?

Historically, the biggest challenge has always been the resistance to change. When I was pushing for cloud adoption at a large telecommunications company, we were called the “rogue ninjas” because it’s often better to ask for forgiveness than permission.

I quickly learned it’s not about the technology itself; it’s about communicating the business value. I had to learn how to translate complex technical concepts into something stakeholders—lawyers, security teams, business leaders—could appreciate. As technologists, we often have our preferences, but there will always be a fear of the unknown. Our job is to make the business value known and explain how it makes their lives simpler.

What emerging technologies and opportunities should businesses be focusing on?

Obviously, it’s AI. There’s a notion that AI will replace developers, but it actually amplifies them. However, for companies to truly leverage AI with their own data, they must focus on their big data initiatives first.

When I was at a digital insurance company, we were very conscious of this. Other companies build first and figure out the data later, but we established our data pipelines and structures from the very beginning. You have to have a solid data foundation because with AI, it’s always “garbage in, garbage out.” You must feed it rich, clean data before you can properly utilise it.

What is the biggest IT-related mistake you see other companies make?

It’s the flawed “build versus buy” decision process. As technologists, we often have an ego that says, “I can always build it better,” without fully understanding the complexity.

The decision should be strategic. You should build if your workflows are highly complex and require deep customisation that you can’t get off the shelf. But if a standard SaaS tool can do the job, you should buy. The mistake is letting a personal preference for a tool or the desire to build something new override a pragmatic analysis of the actual business requirements.

How do you envision the IT sector evolving over the next three to five years?

I believe it will continue to grow. AI is actually lowering the barrier to entry, inviting more people into the IT field who then realise they need to learn the fundamentals.

From an enterprise perspective, I am most excited about the new use cases that will emerge, especially in fintech and insuretech. When I was at the digital insurance company, we were already using data to predict what insurance packages to offer based on a user’s profile. AI will simply boost and amplify these kinds of use cases for every industry.

How are IT leaders navigating the ever-changing regulatory environment?

I’ve noticed a new maturity in the way leaders are approaching AI compared to past technologies like cloud. Before, we would dive in and ask for forgiveness later. With AI, companies are being more careful. They are trying to establish ethical and engineering frameworks first before fully implementing the tools.

For example, in our company, we are ensuring our developers have strong fundamentals before we cascade the widespread use of AI-assisted coding. We see it as an amplifier, not a crutch, and you need a solid foundation to use it effectively.

What is the most critical skill that IT leaders should have today?

I’ve evolved from loving to build products to loving to build the teams that build products. As a tech executive, the most critical skill is not being the best engineer or architect in the room. Your job is to be a multiplier and a connector. A multiplier is someone who can replicate their skills and excellence within their team. A connector is someone who can find the right people to build a harmonious and effective ecosystem. The most critical part of being a tech executive is finding and investing in the right people.

How do you approach mentoring and developing the next generation of IT leaders?

At Stratpoint, I am very focused on building people. I’ve developed several programmes to accelerate the growth of our talent. For example, our “Solutions Designer Cadetship” aims to turn fresh graduates into solutions architects in five years by exposing them to business acumen early in their careers, which is something engineers often lack.

I also have a “Product Builders” programme to encourage a multi-tech stack mindset, moving developers away from fixating on just one technology. I became a CTO at 30, which was a unique and blessed experience. My goal now is to replicate that journey for the next generation by crafting career roadmaps and showing them what’s possible.

What is one question that IT leaders should be asking themselves today?

It’s a two-part question based on a “pay it forward” ethos. First, “What have you done to help another person?” and second, “Have you provided the same kind of opportunity to an up-and-coming talent that you were once given?”

My mentor gave me a chance when I wasn’t ready and helped me get there. It’s easy for leaders to just hire established rockstars. But a real leader asks themselves, “Have I built a rockstar myself?” Have you paid forward the opportunity you once received?