Transformation Director

Program Director - Digital Transformation

About the Role

We are seeking an experienced Program Director to lead complex, enterprise-scale digital transformation initiatives within our organization. This is a critical leadership position for someone who thrives on driving strategic change, managing multiple stakeholder groups, and delivering transformational outcomes in fast-paced, highly regulated environments.

Key Responsibilities

• Lead and direct large-scale digital transformation programs from inception through to successful delivery, ensuring alignment with strategic business objectives
• Manage complex, multi-workstream initiatives involving technology modernization, process re-engineering, and organizational change
• Provide strategic oversight and governance across program portfolios, ensuring effective resource allocation, risk management, and delivery excellence
• Build and maintain relationships with C-suite executives, business leaders, and external partners to drive program success and secure stakeholder buy-in
• Establish robust program management frameworks, methodologies, and best practices to ensure consistent delivery standards
• Lead cross-functional teams including technology, operations, and business units to deliver integrated solutions
• Navigate organizational complexity and manage dependencies across multiple programs and business areas
• Drive cultural and behavioral change to support digital adoption and new ways of working
• Monitor program health, proactively identify and mitigate risks, and implement corrective actions where required
• Champion agile and iterative delivery approaches while maintaining appropriate governance and controls

Essential Experience & Skills

• Proven track record of successfully delivering complex, enterprise-wide digital transformation programs in large, matrixed organizations
• Extensive experience managing programs with budgets exceeding £10M+ and timelines spanning multiple years
• Deep expertise in digital technologies, platforms, and solutions including cloud migration, data platforms, automation, and customer-facing digital channels
• Strong understanding of program management methodologies (Agile, SAFe, Prince2, MSP) with ability to adapt approaches to organizational context
• Exceptional stakeholder management skills with demonstrated ability to influence and engage at all levels including Board and C-suite
• Experience leading organizational change management initiatives alongside technical delivery
• Strong commercial acumen with ability to build business cases and demonstrate value realization
• Excellent problem-solving capabilities with strategic thinking and analytical rigor
• Track record of building and developing high-performing teams
• Experience working in highly regulated industries (financial services, healthcare, utilities, or similar)

Desirable Experience

• Background in the insurance sector or Property & Casualty (P&C) insurance operations
• Understanding of insurance business models, products, and value chains
• Familiarity with insurance-specific technologies and platforms
• Experience of regulatory change programs within financial services

What We're Looking For

We need a dynamic, resilient leader who can navigate ambiguity, drive clarity, and maintain momentum across complex transformation landscapes. You'll be comfortable operating at both strategic and tactical levels, equally at ease presenting to the Board as you are rolling up your sleeves to unblock delivery challenges.

You'll bring intellectual curiosity, a collaborative mindset, and the gravitas to challenge constructively while building consensus. Your leadership style will be authentic, inclusive, and focused on enabling others to succeed.

Our Offer

This role offers the opportunity to shape the future of our organization, leading initiatives that will fundamentally transform how we operate and serve our customers. You'll work with cutting-edge technologies, talented teams, and have genuine autonomy to drive meaningful change.

We offer competitive compensation, comprehensive benefits, flexible working arrangements, and significant opportunities for professional development and career progression.