Digital Strategy & Transformation Consultant

Digital Strategy & Transformation Consultant

About Us

Toucanberry Tech is a boutique consultancy specialising in the reinsurance industry. We combine domain expertise with technical excellence to help financial services and reinsurance clients modernise their systems, automate manual processes, and build smarter platforms.

The 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.

This role sits across strategy, product, and client engagement. You’ll be expected to deal with ambiguity, support robust decision making whilst helping move things forward without the need for ultimate delivery ownership, a true collaborator.

You’ll work closely with engineering teams, offering clear guidance on what to build and why, bringing market context and focus to ensure the most valuable problems are being solved. 

This pivotal role requires someone with C Level gravitas who can articulate a path forward with clarity and conviction, selling the vision and the art of the possible and shape how these capabilities are positioned and client journeys begin through value identification and exemplary story telling skills.