Executive AI Transformation Strategist

HackerTrail; Singapore; On-site; SGD 240,000 - 360,000; Full time

Job summary

HackerTrail in Singapore seeks a Principal Strategist to steer multi-market enterprise transformation engagements, aligning C-suite priorities with our AI-driven capabilities. You shape firm-wide strategy and partner with Architecture leadership to design agentic architectures and measurable business outcomes.

You will mentor Strategists, lead executive discussions, and drive value realization across portfolios while advancing AI adoption at scale across BFSI and telecommunications markets.

Qualifications

• 14–18 years of experience in management consulting, enterprise transformation, or senior leadership roles.
• Experience advising C-suite and board-level stakeholders on enterprise transformation and AI strategy.
• Deep expertise in agentic AI systems, including RAG architectures and multi-agent orchestration.
• Fluency in English across markets is required.

Responsibilities

• Set the strategic direction for enterprise discovery and transformation across a portfolio of client engagements.
• Own and evolve the methodology for business value cases, including cost optimisation and productivity impact.
• Lead executive discussions with C-suite and boards on AI transformation strategy and outcomes.
• Mentor and develop Strategists and contribute to capability-building of the Strategist track.

Skills

AI strategy

RAG architectures

Executive stakeholder leadership

Tools

AWS

AI tooling

Job description

HackerTrail in Singapore seeks a Principal Strategist to steer multi-market enterprise transformation engagements, aligning C-suite priorities with our AI-driven capabilities. You shape firm-wide strategy and partner with Architecture leadership to design agentic architectures and measurable business outcomes.

You will mentor Strategists, lead executive discussions, and drive value realization across portfolios while advancing AI adoption at scale across BFSI and telecommunications markets.