About this role

Provide strategic direction and hands-on consultancy to shape capabilities focused on digitising and automating core processes in the Bermuda or Cayman Islands based Reinsurance markets.
Deal with ambiguity, support robust decision making whilst helping move things forward without ownership.
Work closely with engineering teams, offering guidance on what to build and why.
Articulate a path forward with clarity and conviction, selling the vision and shaping how capabilities are positioned and client journeys begin through value identification and storytelling.

Extensive experience in reinsurance, ideally with exposure to Bermuda or Cayman Islands markets
A self-starter with the ability to operate across executive stakeholders, product teams, and engineering squads bridging the divide between commercial priorities, business needs, and technical delivery.
A strong track record of leading product discoveries and shaping strategic direction for complex programmes.
Experience producing high-quality strategy documents and client-facing deliverables.
Experience with digital transformation and data platform modernisation (especially Actuarial and/or Finance)

Digital Strategy & Transformation Consultant

Key skills