Donavan Cheah

Threat Modeling Complex Systems

I work at the intersection of threat modeling, AI security, offensive security and cyber risk — helping teams understand how systems can fail before attackers demonstrate it for them.

My career began in penetration testing and has since expanded across security architecture, risk and cyber policy. Today, I focus particularly on how threat modeling can help us reason about increasingly complex systems, including AI-enabled systems.

Threat Modeling · AI Security · Security Architecture · Cyber Risk

From breaking systems to understanding how they fail

I studied Physics at the National University of Singapore as a Kent Ridge Scholar before moving into cybersecurity. My first professional lens on security was offensive: identify vulnerabilities, think like an attacker and explain how systems could be made more resilient.

Over time, that question moved upstream. Instead of asking only how a deployed system could be broken, I became increasingly interested in how teams could identify failure modes during design. That led my work into threat modeling, security architecture, cyber risk and, later, cyber policy.

That progression still shapes how I work today: connect attacker thinking with system design, and connect technical findings with decisions that engineers, defenders and leaders can act on.

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Cybersecurity

At Thales Digital Factory, my work focuses on threat modeling, security architecture and offensive security. I am especially interested in threat modeling complex and AI-enabled systems, and in making threat-model outputs useful beyond a design workshop.

I co-lead Threat Modeling Connect Singapore, where we are building a local community of practice and connecting practitioners in Singapore with the wider regional and global threat-modeling community.

I also contribute to cybersecurity research through Kinryū Labs, write on emerging technology and cyber risk through outlets including ISACA, and contribute to initiatives such as the Geneva Dialogue.

Selected Work

A few projects and activities that best represent how I think about cybersecurity: connecting attacker behaviour, system design, operational defence and decision-making.

Threat Modeling & Community

I co-lead Threat Modeling Connect Singapore, mentor teams in the annual TMC Hackathon and help run APAC Threat Modeling Together days.

Speaking & Training

I have delivered talks and training in Singapore and internationally, including DefCamp, SECCON, SINCON and Global Cybersecurity Camp.

Research & Emerging Systems

Through Kinryū Labs, I contribute to research on emerging and unconventional technology environments. The group has presented work at CYSAT Asia and DefCamp.

Defend the Breach

I co-created Defend the Breach, a CISO role-playing experience that asks players to balance limited budgets with critical security operations. It was featured at the Cyber Security Agency of Singapore's Operational Technology Community of Experts Panel.

Technical Roots

Earlier in my career, I created the digitalworld.local series of deliberately vulnerable machines for VulnHub and documented parts of my offensive-security learning journey.

Mentoring & Education

I mentor cybersecurity practitioners through MentorCruise, deliver workshops and career talks, and encourage students to turn their work into conference, hackathon and research opportunities.

Beyond Cybersecurity

Cybersecurity is my professional centre of gravity, but it is not my only interest. I also contribute to sustainability, youth development, community service and neurodiversity advocacy.

My public-service and community work has included participation in the 5th ASEAN-India Youth Summit, work with the PAP Climate Action Group, volunteering with Halogen's Network for Teaching Entrepreneurship, and long-running support for Hair for Hope.

I have also spoken publicly about neurodiversity and Asperger's awareness, including participation in the Purple Parade and school mental-health events.

“We must do justice to the abilities we have been given.”

Speaking, training, research or collaboration?

If you would like to discuss a cybersecurity talk or workshop, threat-modeling collaboration, research, mentoring or community initiative, connect with me on LinkedIn or use the contact form.