Digital Strategy & Transformation Consultant

1 hour, 17 minutes ago
Toucanberry Tech

Toucanberry Tech

Toucanberry Tech is a digital solutions company that specializes in crafting custom software products, deploying efficient cloud services, establishing robust data pipelines, and delivering advanced AI solutions. With a focus on simplicity, elegance, a...

Internet Software & Services

Description

  • Provide strategic direction and hands-on consultancy for digitising and automating core reinsurance processes.
  • Translate deep domain expertise across reinsurance operations, investments, finance, and actuarial functions into product strategy and technology roadmaps.
  • Lead product discovery engagements for reinsurance and financial services clients.
  • Produce insight-driven discovery decks and strategic recommendations.
  • Conduct business analysis across legacy systems and processes to identify automation, integration, and digital transformation opportunities.
  • Present recommendations confidently to senior stakeholders and C-suite audiences to build trust and buy-in.
  • Collaborate with engineering squads to ensure recommendations are technically grounded and deliverable.
  • Help shape how capabilities are positioned and how client journeys begin through value identification and storytelling.

Requirements

  • Extensive experience in reinsurance, ideally with exposure to Bermuda or Cayman Islands markets.
  • Ability to operate across executive stakeholders, product teams, and engineering squads while bridging commercial, business, and technical needs.
  • Strong track record of leading product discovery 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 in Actuarial and/or Finance contexts.
  • Ability to deal with ambiguity and support robust decision-making without ultimate delivery ownership.
  • C-level gravitas with the ability to articulate a path forward clearly and convincingly.
  • Exposure to Actuarial, Investment, or Asset Management consulting in a reinsurance context is preferred.
  • Experience working in or with boutique consultancies is preferred.
  • Interest in applying AI in a practical way to improve delivery and outcomes is preferred.

Benefits

  • Fully remote working arrangement.
  • Outside IR35 B2B contract.
  • Long-term engagement.
  • Target rate of £700 per day.

Interested in this position?

Apply directly on the company website

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