Transformation Office Director

Hiscox

1d • Hybrid

About The Position

As Hiscox drives forward its enterprise‑wide transformation, the Transformation Office Director plays a pivotal leadership role in steering, governing and assuring the delivery of the transformation programme. Operating as a Deputy to the Chief Transformation Officer (CTO), this role provides an enterprise wide lens translating strategy into a a coherent, prioritised and value driven transformation agenda supported by disciplined planning, strong senior alignment, and clear visibility of outcomes, risks and value delivery. You will lead the Transformation Office team responsible for ensuring transformation initiatives are well‑defined, resourced, governed and aligned to strategic ambition. This includes overseeing the Transformation Programme and its core investment buckets (Fit for 10x, Non Fit for 10x, Growth, Resilience & Risk, Small Change, and Innovation Funding) maintaining the integrity and quality of the pipeline, and providing challenge and stewardship around investment decisions. This role acts as a strategic integrator across business units and functions, balancing ambition with capacity, resolving enterprise trade-offs and ensuring that the Transformation investment delivers sustainable commercial, operational and risk outcomes. Success in this role requires exceptional judgement, the ability to navigate senior‑level complexity, and a deep understanding of how to run transformation portfolios at scale. It blends strategic leadership, governance, cross‑functional orchestration, financial stewardship and cultural alignment to ensure Hiscox delivers sustainable, measurable outcomes.

Requirements

• Significant experience leading enterprise‑wide transformation, portfolio governance or PMO functions within complex, multi‑business organisations with transformation budgets of £100m+
• Exceptional strategic judgement, with the ability to translate ambition into structured plans, prioritised portfolios and disciplined governance frameworks.
• Proven ability to challenge constructively, balancing strategic priorities with operational realities and ensuring clarity, accountability and alignment across senior leaders.
• Deep expertise in transformation methodologies, portfolio management, risk management and value‑driven delivery disciplines.
• Strong financial acumen, with experience working closely with Finance on business cases, P&L impacts, investment allocation, benefit realisation and funding governance.
• Demonstrated capability in navigating senior‑level complexity, resolving cross‑functional bottlenecks and enabling effective decision‑making across diverse stakeholder groups.
• Highly skilled communicator, able to simplify complex themes, create compelling executive‑level materials and influence confidently at CEO/GEC level.
• Strong negotiator who can navigate complex multi-stakeholder environments, balancing strategic priorities with operational realities with the ability to demonstrate sound judgement, broker agreements to resolve cross functional bottlenecks and maintain momentum
• Advanced stakeholder management skills, building trust and alignment across Business Units, IT, Finance, HR and corporate functions.
• Experience designing or operating enterprise governance models, including cadence management, decision‑making frameworks, and rigorous reporting structures.
• Proven ability to lead high‑performing teams, creating a culture of clarity, disciplined execution, accountability and collaborative delivery.
• Comfortable operating in environments of ambiguity and pace, bringing structure, foresight and stability to complex transformation portfolios.
• Strong analytical capability, able to interpret data, surface insights, highlight risks and drive focused action across programmes.
• A natural orchestrator and connector, able to bring together disparate stakeholders around shared outcomes and enterprise‑level priorities.
• Committed to continuous improvement, ensuring ways of working, governance and transformation practices evolve and mature over time.

Responsibilities

• Transformation Strategy & Portfolio Leadership Shape and continuously evolve the enterprise transformation roadmap, ensuring that it reflects strategic priorities, sequencing and capacity Provide independent challenge on where we should and should not invest and the timing of these decisions Steward the Transformation Programme, including the Fit for 10x, Non Fit for 10x, Growth, Resilience & Risk, Small Change, and Innovation Funding. Maintaining the integrity of the transformation pipeline; challenging business case quality, scope clarity and delivery plans. Ensure transformation remains tightly aligned to corporate strategy, external context and emerging risks and opportunities
• Leadership of the Transformation Office Build long term organisational capability in transformation leadership, governance and execution Own and evolve the Transformation system, embedding consistent standards, tools, frameworks and disciplines across the enterprise. Establish the Transformation Office as a centre of industry knowledge, insight and judgement
• Executive Governance & Financial Stewardship Design and operate enterprise level governance that enables high quality, timely strategic decisions and discussions regarding transformation progress, including milestones, value delivery, risks, dependencies and key decisions. Partner with Finance to ensure initiatives are underpinned by robust economic logic, clear assumptions and accountability for where the benefits will be delivered. Ensure long‑term sustainability of benefits through clear ownership, transition into BAU, and post‑implementation value tracking. Provide the GEC with insight‑rich materials and perspectives on trade-offs, opportunities and focus areas.
• Enterprise Integration & Constraint Management Act as the arbiter of the constraints within the Transformation programme, resolving cross‑functional bottlenecks that can not be solved within business areas Surface and manage risks, interdependencies and capacity conflicts, supporting timely decision‑making and ensuring alignment across senior stakeholders. Enable constructive tension between ambition and operational reality, creating a sustainable pace of change
• Value Realisation & OKR Tracking Own the approach to value definition, tracking and realisation ensuring that the investment delivers measurable and durable outcomes Tracking realisation of OKRs, outcomes and strategic benefits, surfacing gaps and driving corrective action where required. Ensuring benefits are embedded into BAU ownership and management disciplines.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed