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.

What You’ll Do

• Translate deep domain expertise across Reinsurance Operations, Investments, Finance and Actuarial functions into clear product strategy and actionable technology roadmaps.
• Lead product discovery engagements for reinsurance and financial services clients, producing insight-driven discovery decks and strategic recommendations.
• Conduct business analysis across legacy systems and processes, identifying opportunities for automation, integration, and digital transformation.
• Present confidently to senior stakeholders and C-suite audiences, building trust and shaping buy-in.
• Collaborate with Toucanberry’s engineering squads to ensure strategic recommendations are technically grounded and deliverable.
  

What You Bring

• 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)

Nice to Have

• 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

• Fully Remote
• Outside IR35
• B2B Contract
• Long Term
• Target Rate £700/Day