Chief AI & Data Strategy Leader

Jobtailor; Singapore; On-site; SGD 180,000 - 280,000; Full time

Job summary

Jobtailor seeks a senior AI/ML leader to own the technical strategy for AI-powered intelligence. You will guide architecture, data foundations and governance, partnering with product to shape high-value AI opportunities and scalable delivery across the org.

You will oversee end-to-end lifecycle from data design to deployment, with emphasis on measurable impact, observability and risk management across enterprise datasets.

Qualifications

• 8+ years building production software, data or AI systems.
• Proven record shipping production AI or data systems.
• Strong experience with data pipelines and cloud data platforms.
• Experience with LLMs, retrieval-augmented generation, and evaluation.
• Ability to explain AI strategy and trade-offs to executives.

Responsibilities

• Own the technical strategy, systems, team and operating model for AI-powered intelligence.
• Define AI technical strategy across classification, summarisation, entity resolution, risk detection, insight generation and workflow automation.
• Identify and frame high-value AI opportunities from customer problems and data assets.
• Partner with Product to translate customer needs into measurable product requirements and release sequencing.
• Define technical approaches for use cases including deterministic software, ML, retrieval, LLMs, agents and human review.
• Own end-to-end lifecycle of AI capabilities from data design through deployment, monitoring and improvement.
• Build evaluation systems with golden datasets, regression tests, retrieval-quality checks and KPI tracking.
• Define release-quality standards for observability, tests and traceability.
• Establish governance for model and agent use including prompts, data leakage, tool permissions and audit logs.
• Own data foundations: ingestion, transformation, enrichment, entity resolution and telemetry.
• Architect production AI systems using LLM APIs, open-source models, retrieval and orchestration.

Job description

Jobtailor seeks a senior AI/ML leader to own the technical strategy for AI-powered intelligence. You will guide architecture, data foundations and governance, partnering with product to shape high-value AI opportunities and scalable delivery across the org.

You will oversee end-to-end lifecycle from data design to deployment, with emphasis on measurable impact, observability and risk management across enterprise datasets.