Meet Ronald, who has been at the forefront of SME technology for the past 30 years, advising business owners, boards, and leaders on how to adapt, innovate, and stay ahead in a fast-changing digital landscape. From writing software in the early days of personal computing to pioneering the idea of CTO-as-a-Service, his journey has been shaped by curiosity, courage, and a deep understanding of how businesses must evolve to survive.
A proud recipient of the Spirit of Enterprise Award (2020/2021), Ronald continues to embody the values of resilience, innovation, and leadership. Today, as the founder of Win-Pro Consultancy Pte Ltd, he guides companies through digital transformation, cybersecurity, and AI adoption. His philosophy goes beyond tools and systems; he believes transformation begins with mindset, trust, and people.
After three decades in the technology and SME advisory space, what originally drew you into it, and what convinced you to build Win-Pro across Singapore and Malaysia?
My interest in tech began at six or seven, during visits to People’s Park where I first encountered Radio Shack. It was one of the few places showcasing personal computers and electronic kits. That early exposure sparked my passion.
Later, my father bought me a 286 computer for over three thousand dollars, which was huge investment at the time. From there, I dove into learning what technology could do and how to help others understand it too.
I studied Computer Science at A Levels and NUS, then began building accounting, inventory, and quotation systems for small businesses in Singapore. I didn’t work in big firms. I preferred hands-on programming and impact.
Eventually, I expanded to Malaysia by entrusting a staff member who had to return home. He now leads our offices in Johor Bahru and Kuala Lumpur, 20 years on.
Many business owners still see digital transformation as “upgrading software”. How do you explain the real meaning of digital transformation in 2025, and why is it non‑negotiable for SMEs?
Most people today are only digitising, not transforming. Digital transformation is not simply buying hardware or software. It begins with learning new ways to run, compete and win in a fast‑moving world.
Imagine a business in a vast ocean. Sometimes you face small waves, sometimes big waves, and occasionally a tsunami. If you stop swimming, the waves push you further away from your destination.
Digital transformation starts with mindset change and willingness to learn. It often requires rebuilding the business model entirely. For example, with rising costs, you cannot simply cut salaries. You must redesign your operations, often by outsourcing back‑end work to neighbouring countries.
Your front‑end remains in Singapore, but your back‑end structure changes completely. This requires new workflows, communication systems, SOPs and technology to keep everything seamless.
In short, digital transformation means adopting new ways of working and using technology to support a new business model, not just new tools.
One major blind spot is the belief that “it will never happen to us.” That mindset is like leaving your front door wide open and hoping no one walks in. If the door is open, both good and bad people will enter.
As CTO‑as‑a‑Service, you sit in boardrooms guiding technology strategy and governance. What are the biggest blind spots SME boards have regarding digital and cyber risk?
One major blind spot is the belief that “it will never happen to us.” That mindset is like leaving your front door wide open and hoping no one walks in. If the door is open, both good and bad people will enter.
Businesses need strong basic security, just like homes need locked gates, doors and guards. Cyber security must be taken as seriously as physical security.
Singapore is leading digital transformation and AI strategies for SMEs. What is the biggest misconception leaders have when they start their transformation journey?
The biggest misconception is that digital transformation is about buying tools. In reality, it is about changing habits.
If you have been writing with your right hand all your life and I suddenly ask you to write with your left, it will feel uncomfortable. Companies experience the same discomfort. They struggle because transformation demands new habits, new workflows and new ways of thinking.
Leaders must be open, adaptable and patient with the process.
You have advised hundreds of business owners and C‑suite leaders. What leadership qualities separate companies that thrive from those that struggle during digital disruption?
Leaders who thrive tend to be brave, humble and kind. They learn quickly, take action fast and genuinely care for their teams. They focus on developing people, not just extracting output.
This means understanding what team members want from their careers, sending them for the right training and providing mentoring so they can adapt to new roles.
No one can be hired to do the same job for the next 20 years. Companies that grow are those that help their people grow with them.
What is the most important issue in the world today that needs urgent attention, and why?
The world today is highly de‑globalised, and many global leaders are making decisions that erode trust. We are losing trust in leaders, systems and even one another. When trust disappears, collaboration stops.
If major powers like the US and China do not trust each other, global business suffers. Tariffs appear, restrictions increase and the entire ecosystem becomes harder to operate in.
Technology evolves fast, and collaboration is needed more than ever. Before anything else, the world must fix trust.
What’s your vision for Singapore in the next five years?
Singapore has been positioning itself as a springboard for global businesses. We are a testbed and a strategic launchpad for companies entering Asia.
With Asia expected to be the next major economic engine for the coming decade or more, Singapore will continue to attract global companies looking to expand into the region.
If you could have a superpower for one day, what would it be and why?
I would want the power to see the future and understand the results of the choices I make today. That way, I could avoid mistakes and make better decisions.
I would also use this knowledge to help my team and peers become braver and wiser. When you know what lies ahead, you become bolder and act with more certainty.
Connect with Ronald: WinPro, Facebook and LinkedIn.
