HEAD OF DIGITAL ENABLEMENT

Reporting to: Head of Technology

London

Hiring Timeline: Immediate / ASAP

The Opportunity

Head of Digital Enablement to lead the next phase of digital transformation and unlock the organisation’s ability to deliver meaningful change at pace.

This is a high-impact leadership opportunity for an ambitious and commercially minded digital leader who thrives at the intersection of product thinking, technology delivery and business innovation.

You will create and lead a new operating capability that bridges the gap between idea and execution — establishing cross-functional squads that rapidly test, validate and solve business challenges before they evolve into formal programmes of work.

This role is designed for a leader who combines strategic thinking with hands-on delivery leadership and brings the energy, autonomy and credibility to create momentum across teams and stakeholders.

We are particularly interested in speaking with individuals available immediately or within the coming weeks.

Key Responsibilities

Digital Enablement & Transformation

• Define and establish a digital enablement capability that accelerates delivery across the organisation.
• Create and lead cross-functional squads that rapidly test, iterate and validate business opportunities and operational challenges.
• Embed modern product and agile ways of working to increase speed, quality and business impact.
• Drive adoption of digital tools, frameworks and processes across technology and business teams.
• Act as the connector between emerging ideas and scalable delivery execution.

Product & Delivery Leadership

• Lead teams to identify, prioritise and execute high-value initiatives aligned to business objectives.
• Develop lightweight experimentation and rapid delivery approaches that reduce time from concept to outcome.
• Ensure teams remain outcome-focused and aligned to strategic priorities.
• Build an environment that balances governance, pace and innovation.

Team Leadership & Enablement

• Coach and support squads to remove delivery impediments and continuously improve effectiveness.
• Foster a collaborative, inclusive and high-performing culture.
• Empower teams to make decisions and create accountability through clear ownership.
• Build strong partnerships across technology, operations and business leadership teams.

Rapid Response & Problem Solving

• Respond quickly to changing priorities and emerging opportunities.
• Partner closely with business stakeholders to solve problems where they occur.
• Facilitate agile operating rhythms including stand-ups, sprint planning, retrospectives and reviews.
• Create clarity and momentum in complex and evolving environments.

Continuous Improvement & Performance

• Establish meaningful metrics and reporting to measure squad performance and business outcomes.
• Identify opportunities to improve delivery efficiency and organisational effectiveness.
• Promote experimentation, learning and continuous improvement across teams.
• Drive sustainable delivery practices that support long-term organisational success.

Experience & Capability

We are looking for a leader who brings:

• Significant experience leading Digital Enablement, Product, Digital Delivery or Transformation functions within complex organisations.
• Demonstrated success building and scaling cross-functional teams and agile delivery models.
• Strong product mindset with the ability to connect customer, business and technology outcomes.
• Experience delivering digital transformation initiatives at pace.
• Executive-level stakeholder management and influencing capability.
• Strong commercial judgement and strategic thinking.
• A passion for technology, innovation and creating measurable business impact.
• The confidence to operate autonomously and lead through ambiguity.

Experience within London Market Insurance, Specialty Insurance or Financial Services is highly desirable.

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