
e27 has been nurturing a supportive ecosystem for entrepreneurs since its inception. Our Contributor Programme offers a platform for sharing unique insights.
As part of our ‘Contributor Spotlight’ series, we shine a spotlight on an outstanding contributor and dive into the vastness of their knowledge and expertise.
In this episode, we feature Kevin Shepherdson, CEO and Founder of Straits Interactive, a data privacy solutions provider in ASEAN. Recently recognised as one of Singapore’s top 10 generative AI startup leaders for 2025, Shepherdson is also the author of 99 Privacy Breaches to Beware of and a Fellow in Information Privacy (FIP). With extensive experience consulting for over 50 multinational companies, he is an authorised regional trainer for privacy certification and corporate governance courses at IAPP, Singapore Management University (SMU), and Open Compliance Ethics Group (OCEG).
Thoughts, goals, and journey
After a successful career in senior management at Creative, Sun Microsystems, and Oracle, Shepherdson sought a mid-career shift to pursue more meaningful and impactful work. During a one-year break, he was approached by Savills’ Managing Director to help address Singapore’s 2013 Do-Not-Call (DNC) registry compliance challenge.
This led to the creation of SpiderGate, a Do-Not-Call management solution that quickly gained traction among real estate and insurance firms, surpassing revenue expectations and generating over a million dollars in its first year. This success introduced him to privacy and data protection, laying the foundation for Straits Interactive. The company pioneered a blended model of training, consulting, and software solutions, achieving double-digit growth. During the COVID-19 pandemic, it pivoted from compliance to broader AI and data governance solutions.
Shepherdson said, “By 2023, the launch of ChatGPT revealed the transformative power of Generative AI. We partnered with Microsoft and Rackspace Technologies to introduce the industry’s first AI-powered Data Protection Officer Assistant. Our digital transformation efforts leveraging Gen AI earned us the Most Promising and Outstanding Startup Award in Singapore’s first National Startup award (ACE) .
Today, Straits Interactive has expanded further, offering Generative AI Capability-as-a-Service (CaaS), enabling non-technical professionals to build and deploy AI chatbots, tools, and tutors securely and effectively. The Generative AI landscape is largely driven by developers and data scientists, yet the majority of professionals (trainers, consultants, and entrepreneurs) lack technical expertise to leverage it effectively.”
Shepherdson aims to bridge the gap in Generative AI, making it accessible, practical, and secure for businesses, educators, and professionals worldwide. His goal is to empower them to harness AI’s full potential effectively.
With expertise in data protection and data governance, he authored 99 Privacy Breaches to Beware of and has designed over 20 courses covering these areas, as well as Generative AI—focusing on its value, risks, and constraints. He is currently pursuing a Doctorate in Business Administration, specialising in Generative AI.
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Speaking about the growing adoption of Generative AI, Shepherdson said, “With the rise of Generative AI, we are seeing a significant uptick in interest from business professionals, including those from public agencies. A growing number of non-technical professionals with domain expertise are eager to leverage Generative AI to enhance productivity and learning, signalling a major shift in AI adoption beyond traditional developers and data scientists.
Additionally, organisations are increasingly looking to integrate Generative AI with their internal data while addressing concerns about security, privacy, and compliance. A common trend we’re observing is that many organisations are using off-the-shelf AI tools (e.g., Microsoft Copilot) in a generic manner. Now, they are exploring the development of custom AI solutions tailored to their specific needs.
The emergence of DeepSeek and other open-source LLMs is further disrupting the AI landscape, making AI adoption more cost-effective and accessible. As a result, demand for expertise in prompt engineering has surged—our prompt engineering classes are consistently fully booked, and we leverage our Capabara platform to empower professionals in this area. This trend underscores the broader shift towards AI democratisation, where organisations and professionals across industries are moving from passive AI consumption to actively building and customising AI tools.”
The driving force
Shepherdson is a valuable and active member of our contributor community, sharing his vast insights with the broader ecosystem. He said, “I’m passionate about bridging the gap between technology and business professionals, and being an e27 contributor allows me to share practical insights, demystify AI for businesses, and engage with fellow entrepreneurs. Through this, I hope to drive responsible, sustainable AI transformation and empower startups and enterprises to adopt and scale AI effectively.”
“e27 plays a crucial role in Singapore’s startup ecosystem, serving as a vital platform for entrepreneurs, investors, and innovators to connect, learn, and grow. As a founder working in AI governance and Generative AI adoption, I see e27 as an essential bridge between emerging technology and real-world business applications. Many startups struggle with responsible AI implementation, commercialisation, and ecosystem partnerships, and e27’s community-driven approach fosters the collaboration and thought leadership needed to tackle these challenges,” he added.
Advice for budding thought leaders
Based on his experience in senior leadership positions and writing for various technology publications, Shepherdson advises aspiring thought leaders to focus on three key areas. He said:
- Engage regularly with stakeholders and the media
To establish yourself as a trusted industry voice, make it a habit to engage with your stakeholders—whether they are clients, partners, or industry peers. If opportunities arise, interact with the media (yes, I know it can be nerve-racking), but remember that thought leadership is more than just promoting your products and services. Instead, educate and provide value by sharing industry insights, trends, and expert opinions.
By doing this, you position yourself as a go-to expert, and when the media or organisations need an industry voice, they will think of you first.
- Participate in industry events and panel discussions
One of the most effective ways to build credibility is by actively participating in industry events, conferences, and panel discussions (I know it is time consuming). These platforms allow you to: share your expertise in a public forum, engage in meaningful conversations with industry leaders, and gain visibility and recognition for your insights.
Additionally, be generous with your knowledge (I know a few of my competitors — especially consultants and legal firms will charge for giving professional advice). Offer guidance and advice to those who seek it without expecting immediate returns. Thought leaders give before they receive, and by providing genuine value, you build long-term credibility and influence.
- Leverage Generative AI for communication—but thoughtfully
Generative AI can be a powerful tool to help structure your key points, refine messaging, and enhance your communication. However, never rely passively on AI-generated responses. Instead, use it as an idea-generation tool to: organise and articulate your thoughts more effectively, validate your insights with additional perspectives, and fine-tune the clarity and impact of your message.
According to Shepherdson, authenticity is key; thought leaders should share their own expertise and insights, not just AI-generated content, to build credibility and impact.
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Juggling too many things?
Shepherdson acknowledges the challenge of balancing work, industry contributions, and personal life, especially as a startup founder. He emphasises the importance of a strong support system and shares three key strategies for maintaining personal and professional growth.
- Adopt a growth mindset – Continuous learning is crucial, even for experienced professionals who often struggle to make time for self-development.
- Prioritise learning – Despite a demanding schedule, Shepherdson pursued a Doctorate in Business Administration specialising in Generative AI, emphasising the value of lifelong education.
- Create space for work and personal life – Balance isn’t about daily perfection but knowing when to shift priorities to sustain long-term success.
Staying in the loop
According to Shepherdson, staying updated in the industry requires continuous learning and active engagement with emerging trends. He ensures this by designing new courses that cover the latest developments, pushing himself to stay deeply connected with industry shifts. His dedication to lifelong learning was recognised with Singapore’s SkillsFuture Fellowship, awarded by the President, honouring individuals who consistently upskill, mentor, and contribute to knowledge sharing.
As the leader of a Generative AI capability platform, Shepherdson is immersed in AI daily, collaborating with developers, consultants, and industry experts. Through extensive research, experiments, and real-world applications, he explores how Generative AI can drive innovation across sectors. National-level prompt design competitions have further exposed him to how learning institutions and SMEs are integrating AI to enhance productivity and education.
He also highlights the value of social media and podcasts in staying informed. Engaging with relevant videos or discussions helps professionals leverage AI-driven content recommendations, ensuring they remain up to date with industry advancements.
Take a look at his articles here for more information and perspectives on his expertise.
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