VP, Guidewire Transformation

Fulcrum Digital Inc; Greater London; Hybrid; GBP 180,000 - 260,000; Full time

Job summary

Fulcrum Digital. VP, Guidewire Transformation will lead a major cloud-driven transformation for a London Market insurer, overseeing the Guidewire Cloud delivery, PAS migration, and governance across the transformation lifecycle.

The role requires 12+ years in insurance transformation, 2+ Guidewire implementations, and deep knowledge of Lloyd's, brokers, and MGAs. A senior, business-facing leader who can manage vendors and regulatory requirements is needed.

Qualifications

• 12+ years of leadership in insurance transformation.
• At least 2 full Guidewire implementations led.
• Deep London Market knowledge (Lloyd's, brokers, MGAs).
• Strong executive presence and stakeholder management.

Responsibilities

• Own the transformation roadmap, business case, and benefits realization.
• Lead Guidewire Cloud delivery across PolicyCenter, BillingCenter, and ClaimCenter.
• Migrate legacy PAS systems, including data conversion, cutover, and decommissioning.
• Align delivery with London Market change initiatives, including Lloyd's Blueprint Two.
• Manage SI and vendor partners on scope, budget, and SLAs.
• Drive process redesign and adoption with business leaders.
• Own governance and executive reporting to the Senior Leadership Team (SLT).
• Ensure regulatory compliance with PRA, FCA, and DORA requirements.

Skills

Insurance transformation

Guidewire leadership

London Market knowledge

Vendor management

Executive presence

Stakeholder negotiation

Regulatory awareness

Job description

Fulcrum Digital is a global AI-first enterprise transformation company with over 25 years of experience. We partner with enterprises across financial services, insurance, healthcare, retail, manufacturing, higher education, and logistics to move from AI experimentation to scalable business outcomes. Fulcrum Digital works with over 100 global clients, including Fortune 500 enterprises, combining deep industry expertise with capabilities in enterprise AI, digital engineering, cloud modernisation, platform integration, and generative AI.

The Role

We are looking for a VP, Guidewire Transformation to join one of our top client engagements — a leading London Market insurer — to drive a large-scale Guidewire Cloud transformation and legacy Policy Administration System (PAS) migration. This is a senior, business-facing leadership role spanning the full transformation lifecycle: roadmap and business case ownership, Guidewire Cloud delivery, legacy system decommissioning, and executive governance, all within the context of London Market change initiatives including Lloyd's Blueprint Two. This is a hybrid contract role based in London, UK, requiring four days per week onsite from Monday to Thursday.

What You'll Do

• Own the transformation roadmap, business case, and benefits realization
• Lead Guidewire Cloud delivery across PolicyCenter, BillingCenter, and ClaimCenter
• Migrate legacy PAS systems, including data conversion, cutover, and decommissioning
• Align delivery with London Market change initiatives, including Lloyd's Blueprint Two
• Manage SI and vendor partners on scope, budget, and SLAs
• Drive process redesign and adoption with business leaders
• Own governance and executive reporting to the Senior Leadership Team (SLT)
• Ensure regulatory compliance with PRA, FCA, and DORA requirements

Requirements

• 12+ years of experience in insurance transformation leadership
• 2+ full Guidewire implementations delivered in a lead role
• Deep London Market knowledge, including Lloyd's, brokers, and MGAs
• Strong experience managing SI partners and budgets
• Strong executive presence and influence
• Outcome-driven and decisive approach
• Clear communicator and skilled negotiator