CTO – Guidewire Transformation

Chief Technology Officer (CTO) – Insurance Technology (Guidewire) Transformation

Location: United Kingdom (Hybrid/Flexible)

Employment Type: Permanent

Overview

Our client is a highly ambitious and rapidly evolving insurance organisation undertaking a significant technology and business transformation programme. To support the next phase of growth, they are seeking an exceptional Chief Technology Officer (CTO) to define and execute the company's technology strategy while leading large-scale transformation initiatives across the enterprise.

This is a rare opportunity for a technology executive with deep insurance domain expertise, proven C-suite leadership experience and a track record of delivering complex core platform modernisation programmes within major insurers.

The successful candidate will play a pivotal role in shaping the future technology landscape of the organisation, driving innovation, operational excellence and digital transformation across all business functions.

Key Responsibilities

Technology Leadership & Strategy

• Define and execute the organisation's long-term technology vision and roadmap.
• Act as a key member of the Executive Leadership Team, advising the Board and senior stakeholders on technology strategy and investment.
• Ensure technology capabilities directly support business growth, operational efficiency and customer experience objectives.
• Lead enterprise architecture, technology governance and innovation initiatives.

Insurance Core Systems Transformation

• Lead large-scale transformation programmes involving insurance core platforms and policy administration systems.
• Drive implementation, optimisation and strategic development of Guidewire and associated insurance technology ecosystems.
• Oversee modernisation of legacy systems and migration to cloud-native architectures.
• Ensure seamless integration across underwriting, claims, policy administration, billing, data and digital platforms.

Technology Delivery & Operations

• Lead global technology teams including Architecture, Engineering, Infrastructure, Cloud, Security, Data and Delivery functions.
• Establish high-performing engineering and product organisations.
• Drive Agile, DevOps and modern software engineering practices.
• Ensure platform resilience, scalability, performance and operational excellence.

Digital, Data & Innovation

• Champion emerging technologies including AI, automation, analytics and digital customer engagement.
• Develop data-driven capabilities that support underwriting, claims, pricing and operational decision-making.
• Identify opportunities for innovation and competitive advantage through technology.

Risk, Governance & Regulatory Compliance

• Ensure compliance with insurance regulatory requirements, cybersecurity standards and governance frameworks.
• Manage technology risk, business continuity and operational resilience.
• Maintain robust security, data protection and cloud governance standards.

Required Experience

Essential

• Previous experience as CTO, Chief Architect, Technology Director, CIO or equivalent executive leadership role.
• Extensive experience within the insurance sector, ideally across P&C, General Insurance, Specialty Insurance or London Market environments.
• Proven track record delivering large-scale enterprise transformation programmes exceeding £50m+ in value.
• Deep expertise in Guidewire InsuranceSuite including:
• PolicyCenter
• ClaimCenter
• BillingCenter
• Guidewire Cloud
• Digital Portals
• Data and Analytics solutions
• Integration Frameworks and APIs
• Experience leading cloud transformation programmes (AWS, Azure and/or Google Cloud).
• Strong understanding of enterprise architecture, integration strategy and modern technology operating models.
• Experience managing large global technology organisations and multi-million-pound budgets.

Highly Desirable

• Experience within Lloyd's and London Market insurance environments.
• Exposure to complementary insurance platforms such as Duck Creek, Majesco, EIS, Sapiens or Fadata.
• Experience delivering AI, automation and advanced analytics initiatives.
• Prior consulting or transformation leadership experience within major insurance consultancies.

Leadership Profile

The successful candidate will demonstrate:

• Exceptional executive presence and stakeholder management skills.
• Ability to influence Board-level decision making.
• Strategic vision combined with strong delivery execution.
• Commercial acumen and business-focused technology leadership.
• Strong people leadership and organisational transformation capability.
• Passion for innovation and continuous improvement.

What's On Offer

• Opportunity to lead one of the most significant technology transformation programmes within the insurance sector.
• Executive-level compensation package.
• Performance-related bonus.
• Long-Term Incentive Plan (LTIP) / Share Options.
• Comprehensive executive benefits package.
• Flexible and hybrid working environment.
• Significant influence over future technology and business strategy.

Package: Exceptional Executive Compensation Package including Competitive Base Salary, Performance Bonus, LTIP / Share Options, Executive Benefits and Pension

This position represents an outstanding opportunity for a transformational technology leader to shape the future of a growing insurance organisation whilst benefiting from substantial long-term value creation through executive equity participation.