Guidewire Delivery Director

Guidewire Delivery Director (UK)

Location:

UK (Hybrid / Remote + Onsite as required)

Employment Type:

Permanent

Industry: Insurance / Digital Transformation

Reports to:

Programme Director / CIO

We are seeking an experienced Guidewire Delivery Director to lead and oversee end-to-end delivery of Guidewire solutions across Policy Center, Claim Center, Billing Center, and associated digital, integration, and data work streams. This is a senior leadership role responsible for shaping delivery strategy, driving execution, ensuring alignment with business needs, and successfully managing cross-functional teams, system integrators, and key stakeholders.

The ideal candidate is not required to be a deep technical expert, but must have a strong understanding of Guidewire platforms, insurance operations, and enterprise technology delivery. This person will bring a proven track record of overseeing large-scale transformation projects and managing multiple concurrent work streams within complex insurance environments.

• Lead end-to-end delivery of Guidewire products (Policy Center, Claim Center, Billing Center) across all phases of the delivery lifecycle.
• Own delivery strategy, planning, governance, and execution.
• Ensure solutions meet business objectives, regulatory requirements, and agreed SLAs.
• Drive programme performance, identifying risks, dependencies, and mitigation options early.

• Act as primary delivery contact for senior internal stakeholders (C-level, Heads of Business, Technology).
• Manage third-party SI partners, Guidewire specialists, offshore teams, and internal teams.
• Ensure alignment between business, IT, and delivery partners throughout the project.

• Manage programme budgets, forecasts, business cases, and financial tracking.
• Ensure commercial value from vendors, contractors, and SI partners.
• Report on programme health, progress, resource utilisation, and key KPIs.

• Lead cross-functional delivery teams including BAs, PMs, Tech Leads, Architects, and Test teams.
• Drive a culture of accountability, collaboration, and continuous improvement.
• Support team development, coaching, and performance management.

• Implement best-practice delivery frameworks (Agile, Waterfall, Hybrid).
• Ensure high-quality documentation, governance, compliance, and assurance.
• Oversee cutover planning, environment readiness, UAT, release management, and hypercare.

• Maintain an up-to-date understanding of Guidewire applications, configurations, and integration patterns.
• Translate business requirements into delivery plans and feasible technical approaches.
• Understand the implications of configuration vs customisation, cloud vs on-prem, and integration with experience & Skills

• 10+ years’ experience in IT delivery or programme management, ideally within Insurance.
• Proven track record delivering large-scale transformation programmes (£5m–£25m+).
• Direct experience overseeing delivery of Guidewire products (Policy Center, Billing Center, Claim Center).
• Experience managing SIs, external vendors, and multi-disciplinary delivery teams.

• Strong understanding of the Guidewire suite and insurance business processes.
• Excellent leadership, communication, and stakeholder management skills.
• Solid financial management and budget oversight.
• Ability to make informed decisions under pressure and navigate complex environments.
• Strong problem-solving, prioritisation, and governance capability.

• Experience with Guidewire Cloud implementations.
• Background working with General Insurance (GI), Specialty, or London Market.
• Familiarity with integration middleware, data platforms, and digital front-end technologies.

• Opportunity to lead high-impact transformation across core insurance operations.
• A collaborative, forward-thinking technology and delivery environment.
• Long-term career progression within a rapidly evolving digital organisation.