Head of Technology

ABOUT US:

PolicyStreet is a leading InsurTech group, specialising in innovative digital insurance solutions for businesses and consumers in Southeast Asia and Australia. With a network of over 40 providers, we offer a comprehensive range of products, including embedded insurance, customised employee benefits, financial advisory, and digital solutions – making insurance straightforward, for everyone. Through our regional group of companies, we serve more than 5 million customers with over US$ 10 billion in sum insured.

ABOUT THE ROLE:
The ideal candidate is a hands-on solution-oriented and commercially astute technology leader who can balance innovation with speed, cost, and return on investment (ROI) in a fast-moving InsurTech environment. This person translates complex business challenges into practical, scalable digital solutions with measurable impact.

WHAT YOU’LL DO:

• Act as a thought leader and a part of the Senior Leadership Team to drive technology strategy alignment with the company's business objectives and growth plans.
• Lead and drive the technology team with a strong focus on speed-to-market, scalability, and operational resilience. Continuously improve processes, and ways of working within the technology team. 
• Translate and communicate complex business needs and technical challenges into clear concepts, decision frameworks, recommendations and effective IT solutions to respective stakeholders as needed. 
• Own and manage the technology budget, vendor strategy, and sourcing decisions to maximize value. Apply strong commercial wisdom to evaluate and communicate the cost of delay, opportunity cost, and ROI with priorities on business impact.
• Act as a catalyst for change, leading transformation initiatives with resilience and precision. Proactively identify potential risks, delays and issues early in order to manage expectations and prevent surprises.

WHAT WE EXPECT OF YOU:

• 6~8+ years of progressive experience in technology, digital, or engineering roles, with at least 2–3 years in a senior leadership capacity (e.g. Head of Technology, CTO, VP Engineering, Head of Digital).
• Strong preference for experience in startups, or scale-ups in InsurTech, Insurance, FinTech, Banking, Digital Business or other regulated financial services.
• Proven track record of owning and delivering end-to-end technology strategy and execution in a growth-oriented or transformation-driven environment.
• Strong commercial judgment.
• High resilience and decisiveness in navigating ambiguity, rapid change, and competing priorities.
• Strong problem-solving skills  with solutioning mindset in environments with incomplete information or evolving requirements.
• Exceptional ability to communicate complex technical, digital, and analytical concepts clearly and persuasively to non-technical stakeholders.
• Understanding of modern technology stacks including cloud platforms, APIs, data platforms, and analytics.