Principal AI 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

About the role

The Role The Principal Strategist sets the strategic direction for our most complex, multi-market enterprise transformation engagements, connecting C-suite business priorities with our technical and delivery capabilities at a portfolio level. This role is responsible for shaping firm-wide AI-driven transformation strategy, designing enterprise-grade agentic architectures in partnership with Architecture leadership, driving portfolio-level business outcomes, and building trusted advisory relationships with executive leadership. What You Will Do Set the strategic direction for enterprise discovery and transformation approaches across a portfolio of complex, multi-market client engagements. Own and evolve the methodology for measurable business value cases, including cost optimisation, productivity improvement, operational efficiency, risk reduction, and revenue impact metrics used across the practice. Partner with Architecture and Engineering leadership to shape enterprise-grade agentic architectures, operational models, and reusable AI-enabled business process patterns. Lead C-suite and board-level stakeholder discussions, acting as a trusted advisor on AI transformation strategy and enterprise outcomes. Mentor and develop Strategists and Senior Strategists, and contribute to the growth and capability-building of the Strategist track.

What you'll bring

What We Are Looking For 14-18 years of experience in management consulting, enterprise transformation, enterprise technology strategy, or senior leadership roles within BFSI or Telecommunications environments, with a track record of leading complex, multi-market programmes. Established experience advising C-suite and board-level stakeholders on enterprise transformation and AI strategy. Deep expertise in agentic AI systems, including RAG architectures, multi-agent orchestration, human-in-the-loop workflows, AI evaluation, and enterprise AI adoption at scale. Deep familiarity with AWS services related to AI, agentic workflows, and data modernisation is required. Strong commercial acumen, with experience owning account-level or portfolio-level value realization and growth outcomes. Ability to set and uphold standards for implementation-ready functional specifications, workflow diagrams, integration requirements, and business process documentation across teams. Fluency in spoken and written English is required across all markets.

Benefits and perks

What We Offer Highly competitive compensation aligned to market standards for senior practice leadership. Opportunities to shape and lead our most strategic AI transformation programmes across Asia Pacific. Deep exposure to advanced AI tooling, AWS partnership ecosystems, and cross-market executive relationships in a fast-moving and collaborative environment.