Crossover Search Pte. Ltd. Hiring! Full Time Deputy Director, IT in - Ricebowl

We are partnering a leading healthcare organisation to appoint a Deputy Director – IT, a senior technology leadership role supporting the organisation’s digital transformation, IT operations, data and AI agenda.

This is an opportunity to help shape how technology, data, AI and digital capabilities come together to support high-quality care across a complex, multi-site healthcare environment.

The Role

Working closely with the Head of IT, you will help drive both strategic direction and operational execution across the organisation’s technology landscape.

You will oversee key areas spanning IT operations, enterprise systems, infrastructure, cybersecurity, data and AI, software delivery and technology transformation, while developing a capable and future-ready IT team.

As the department’s second-in-command, you will also provide leadership continuity and step into the Head of IT role when required.

Key Priorities

• Develop and drive the organisation’s enterprise AI and Data Strategy, including data, AI and automation initiatives
• Translate IT strategy and roadmaps into executable programmes, projects and operational plans
• Strengthen the reliability, resilience and performance of IT services across a distributed network of care facilities
• Lead major system implementations, technology projects and digital transformation initiatives
• Strengthen cybersecurity, IT governance, business continuity and disaster recovery capabilities
• Build internal software engineering and solution delivery capabilities, reducing reliance on outsourced development
• Drive adoption of Agile ways of working and a culture of continuous improvement
• Strengthen vendor, contract and service-level management
• Support technology budgeting, resource planning and cost optimisation
• Build and develop a high-performing, future-ready IT team

What We’re Looking For

• Approximately 10–15 years of IT experience, including at least 5 years in leadership roles
• Strong experience across IT operations, systems implementation and project delivery
• Good understanding of enterprise infrastructure, cybersecurity and applications
• Experience leading digital transformation, data, AI or automation initiatives
• Strong stakeholder and vendor management capability
• Ability to operate both strategically and hands-on, translating direction into execution
• Experience in healthcare or similarly complex, multi-site environments would be advantageous
• Degree in Computer Science, Computer Engineering or a related discipline; postgraduate qualifications are advantageous

Why This Role

This role sits at the intersection of technology, transformation and care delivery.

It offers the opportunity to:

• Shape the organisation’s next phase of digital and AI transformation
• Strengthen technology capabilities across a complex healthcare environment
• Build greater internal ownership of critical digital solutions
• Develop a future-ready IT organisation and team
• Make a tangible impact on operational effectiveness and the delivery of quality care

If this aligns with your experience, we would be keen to hear from you. Apply directly or reach out for a conversation.