CEO Insights Magazine

A CEO is central to a company's progress, driving growth, fostering innovation, and ensuring long-term success. A visionary leader shapes the strategic direction while cultivating a culture of resilience and adaptability. Kevin Shepherdson, Founder of Straits Interactive reflects this approach. His company is a pioneering force at the intersection of data privacy and generative AI. Since its founding in 2013, Straits Interactive has pioneered innovative solutions in privacy compliance and has recently made significant strides in leveraging generative AI to help businesses enhance productivity and create value. With a strong focus on customer-centric solutions, Kevin has successfully steered the company through multiple phases of growth, while ensuring it stays ahead of industry trends.

Beyond his professional achievements, Kevin’s passions for genealogy and music reflect his multifaceted personality. A skilled musician and a recipient of the prestigious SkillsFuture Fellowship Award, Kevin’s journey is a testament to his dedication to both technology and people. In this article, we explore Kevin’s path from corporate leader to startup founder, his vision for Straits Interactive, and his leadership philosophy in building a company that blends innovation with simplicity. Let’s dive in to know more.

Having transitioned from building your career in leading MNCs to now leading your own startup, what have been the key achievements and challenges that have defined your journey?
Before founding my startup in 2013, I gained valuable experience working with leading multinational companies in the tech industry. I began my career at Creative Technology, where I contributed to the development of the Sound Blaster and helped revolutionize multimedia. A standout achievement was impressing the late CEO Sim Wong Hoo at a distributor conference by showcasing my musical talent with a live sound simulation, which led to key roles in the company’s product development.

Afterward, I joined Sun Microsystems, where I created a Business Intelligence System that earned me a Global Marketing Intelligence Excellence Award. My time at Oracle Asia Pacific involved leading demand generation and customer intelligence with a $400 million sales target. A major challenge during Oracle’s acquisition of Sun was managing redundancies and transitioning a team from Singapore to Manila.

Seeking new opportunities, I briefly left the corporate world and then helped real estate agents adapt to Singapore’s Do-Not-Call Registry when the Personal Data Protection Act was introduced. This led to the creation of an automated solution for compliance, which became highly successful, generating over a million dollars in revenue by the end of the first year. This success sparked the foundation of Straits Interactive, initially focused on privacy solutions and training for PDPA compliance. Today, Straits Interactive has evolved to leverage generative AI, providing a competitive edge in the market.

How do you leverage these experiences to strengthen Straits Interactive's position as a Generative AI company in the tech sector?
As Singapore enforced the Personal Data Protection Act (PDPA) and ASEAN countries introduced similar laws, our business grew rapidly. However, COVID-19 disrupted this growth, forcing us to pivot towards data governance and align business goals with compliance requirements. During this period, we became one of the first to introduce a Data Ethics and AI Governance course in partnership with Singapore Management University Academy (SMUA) alongside our privacy software.

In late 2022, my business partners and I recognized the potential of generative AI, especially ChatGPT, but also the associated risks. Instead of focusing solely on AI governance, we decided to first evangelize the benefits of generative AI, later addressing the ethical, privacy, and security risks. We applied our approach from data protection to simplify and operationalize generative AI concepts.

We broadened our scope from privacy to AI as a service, collaborating with Microsoft and Rackspace to launch the first AI-powered Data Protection Officer (DPO) Assistant. Our innovation continued with the development of Capabara, our generative AI platform, enabling organizations to implement AI securely and efficiently, even without AI expertise. We are also committed to upskilling our staff in generative AI, ensuring they understand both the opportunities and risks this technology presents.

How have you guided the company in building a strong expertise in data privacy and protection under your leadership?
Building expertise in data privacy and protection was challenging, as it’s often viewed as a legal domain. To address this, I partnered with privacy law expert Lyn Boxall and former regulator William Hioe to bridge legal and operational compliance. We collaborated with the International Association of Privacy Professionals (IAPP) to offer certified training for Data Protection Officers (DPOs), ensuring our team delivered highquality services. I also partnered with SMU Academy to make Singapore a regional hub for data privacy, offering over 40 courses. Our co-authored book ‘99 Privacy Breaches to Beware Of’ gained international recognition. Additionally, we launched Singapore’s first Hands-on DPO Course, combining consultancy with practical software tools.

How do you lead your team in helping businesses harness the potential of generative AI to boost productivity, while also managing associated risks and ethical concerns?
Our approach to generative AI is rooted in simplicity, user-friendliness, and operational efficiency. Along with my business partners, Alvin and Celine, we focus on making processes scalable and repeatable, incorporating governance frameworks and ISO standards to align with industry norms. This ensures smooth internal knowledge transfer and easier adoption for clients. Our Capabara platform helps users apply generative AI in real-world scenarios, guiding them through the AI maturity lifecycle while addressing risks and ethical considerations. I lead my team to act as trusted advisors, emphasizing the importance of having a Roadmap, Reliability, and Relationship to build long-term trust and manage the challenges of generative AI effectively.

How do you identify key characteristics for securing valuable alliances, and how does that fit into your future roadmap?
In the early stages of a startup, alliances are crucial, but it's important to be cautious of promises based solely on reputation. Over time, I’ve learned that forming strategic relationships with established players like Microsoft, Singapore Management University Academy (SMUA), privacy regulators, and global organizations such as IAPP has been key to our success. When considering potential partnerships, I look for mutual value, alignment with our core values, and long-term goals. For us, equity in partnerships is essential, as both sides must benefit for the relationship to thrive.

Looking ahead, our roadmap is focused on continuous innovation, inspired by success stories like CaseText. We aim to leverage generative AI to enhance productivity, enabling clients to move from passive consumers to active creators of value. Our focus will remain on understanding customer pain points and empowering them to innovate with AI. By prioritizing customer needs and fostering value creation, we believe sustainable growth will follow.

What advice would you offer to emerging leaders looking to set benchmarks in Generative AI through their efforts?
For leaders entering the generative AI space, it’s crucial to take a forward-thinking approach. You can either bet that current AI technology is near its peak or expect significant improvements. Embracing the latter allows you to create scalable, adaptable solutions that evolve with AI advancements. For instance, an AI tutor designed to grow in sophistication with each new model can support users at various educational levels. In contrast, focusing on short-term limitations can make your solution vulnerable to future technological progress. My advice is to build flexible solutions that evolve with AI, prioritize customer outcomes, and remain adaptable for long-term success.

Kevin Shepherdson,  Founder, Straits Interactive 
Kevin Shepherdson is the Founder of Straits Interactive, a leading provider of data privacy and generative AI solutions. With extensive experience in tech and data governance, Kevin has built strategic alliances with industry giants like Microsoft, IAPP and Singapore Management University Academy (SMUA), driving innovation and growth in the AI space.