Job Type:
Permanent
Build a brilliant future with Hiscox
Transformation Office Director
Reporting to: Chief Transformation Officer
Location: London, York or Colchester
Advert closing date: 13th March 2026
About the Role
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.
What You’ll Be Doing
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.
Person Specification
- 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.
About Hiscox
As an international specialist insurer we are far removed from the world of mass market insurance products. Instead we are selective and focus on our key areas of expertise and strength - all of which is underpinned by a culture that encourages us to challenge convention and always look for a better way of doing things.
We insure the unique and the interesting. And we search for the same when it comes to talented people. Hiscox is full of smart, reliable human beings that look out for customers and each other. We believe in doing the right thing, making good and rebuilding when things go wrong. Everyone is encouraged to think creatively, challenge the status quo and look for solutions.
Scratch beneath the surface and you will find a business that is solid, but slightly contrary. We like to do things differently and constantly seek to evolve. We might have been around for a long time (our roots go back to 1901), but we are young in many ways, ambitious and going places.
Some people might say insurance is dull, but life at Hiscox is anything but. If that sounds good to you, get in touch.
Diversity and Hybrid working
At Hiscox we care about our people. We hire the best people for the job and we’re committed to diversity and creating a truly inclusive culture, which we believe drives success.
We have also learned over the past few years that working life doesn’t always have to be in the office, and now it is safe to do so we have introduced hybrid working to encourage a healthy work life balance.
This hybrid working model is set by the team rather than the business to enable you to manage your own personal work-life balance. We see it as the best of both worlds; structure and sociability on one hand, and independence and flexibility on the other.
Apply now for further information
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