[Hiring] Digital Strategy & Transformation Consultant @Toucanberry Tech

Role Description

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.

• Deal with ambiguity and support robust decision making.
• Help move things forward without the need for ultimate delivery ownership.
• Work closely with engineering teams, offering clear guidance on what to build and why.
• Bring market context and focus to ensure the most valuable problems are being solved.
• Articulate a path forward with clarity and conviction, selling the vision and the art of the possible.
• Shape how capabilities are positioned and client journeys begin through value identification and exemplary storytelling skills.

Qualifications

• 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.
• 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).

Requirements

• Exposure to Actuarial, Investment, or Asset Management consulting in a reinsurance context.
• Experience working in or with boutique consultancies.
• Interest in applying AI in a practical way to improve delivery and outcomes.

Benefits

• Fully Remote.
• Outside IR35.
• B2B Contract.
• Long Term.
• Target Rate c£700 per day.