About the Role
We are seeking a highly accomplished and results-oriented Associate Director, Software Engineering to lead the strategy, development, delivery, and operations of a critical application portfolio.
The role will oversee both customer-facing applications, including Cast.sg, Insurance Application and Regional Rewards, as well as foundational backend systems through the Open Platform.
The successful candidate will be a strong technical leader and strategic thinker with proven experience in building and scaling engineering organisations, modernising application architecture, managing technology partners, and delivering reliable software products at scale.
Key Responsibilities
1. Technical Strategy & Architecture
- Define and execute the technical roadmap and architectural vision across the application portfolio.
- Drive the design of scalable, highly available, secure and high-performance applications on AWS Cloud.
- Lead application modernisation, platform evolution and technology transformation initiatives.
- Establish and promote best practices across CI/CD, observability, automated testing, DevOps and software engineering quality.
- Provide technical direction and hands-on guidance across Java, React, Next.js, AWS, PostgreSQL and SQLtechnologies.
- Ensure technical architecture and engineering practices support long-term business and product objectives.
2. Engineering Leadership & People Management
- Lead multiple software engineering teams and Senior Engineering Managers.
- Mentor, coach and develop engineering leaders and technical talent.
- Establish a culture of technical excellence, accountability, collaboration and continuous improvement.
- Oversee the complete Software Development Lifecycle (SDLC) from planning and design through development, testing, deployment and production operations.
- Ensure timely, predictable and high-quality delivery of software products and projects.
- Drive talent acquisition, succession planning, employee development, retention and performance management.
3. Vendor & Strategic Partner Management
- Own strategic relationships with key technology vendors, outsourcing partners and external service providers.
- Manage vendor performance, contractual deliverables, Service Level Agreements (SLAs) and service quality.
- Lead vendor due diligence, technology risk assessments and compliance reviews.
- Negotiate and manage technology contracts to optimise cost, quality and business value.
- Drive cost optimisation across key technology services, including AWS infrastructure and proprietary platform licences.
4. Stakeholder & Executive Management
- Act as the primary technical interface with executive leadership, Product Management, Finance and regional business stakeholders.
- Balance and prioritise competing technology and business requirements across the application portfolio.
- Communicate technical risks, delivery status, architectural decisions and strategic initiatives clearly to technical and non-technical stakeholders.
- Translate complex technical matters into business impact, risks, opportunities and actionable recommendations.
- Build strong relationships across product, technology and regional business teams.
5. Application Portfolio Oversight
Open Platform
- Drive the strategic evolution of core services, APIs and backend capabilities supporting consumer applications.
- Ensure platform services are robust, scalable, secure and easy to integrate.
Customer-Facing Applications
- Provide leadership oversight for Cast.sg, Insurance Application and Regional Rewards.
- Ensure high-quality user experiences, feature delivery and integration with regional partner systems.
- Align application development with product strategy, customer needs and business objectives.
Skills & Experience
- Minimum 10 years of progressive experience in software engineering, with at least 5 years in an engineering leadership or senior management role.
- Proven experience managing and scaling multiple software engineering teams.
- Strong track record in software architecture, application modernisation and technology transformation.
- Demonstrated experience managing technology vendors and external partners, including contract negotiation, SLA management and performance monitoring.
- Strong hands-on technical understanding of:JavaReact / Next.jsMicroservices architecturePostgreSQL / SQL AWS Cloud, including services such as ECS, Lambda, RDS and S3.
- Extensive experience across the full Software Development Lifecycle (SDLC) and Agile/Scrum methodologies.
- Experience operating high-availability, customer-facing applications in cloud environments.
- Strong understanding of software engineering practices including CI/CD, automated testing, observability, security and performance optimisation.
- Excellent leadership, communication, stakeholder management and problem-solving skills.
- Ability to present complex technical strategies and recommendations to executive and non-technical audiences.
