Underwriting Transformation Lead

Chaucer is a leading insurance group at Lloyd's, the world's specialist insurance market. We help protect industries around the world from the risks they face. Our customers include major airlines, energy companies, shipping groups, global manufacturers and property groups. Headquartered in London, with international hubs in Copenhagen, Dubai, Miami, Dublin, Singapore, Sydney and Bermuda, to be closer to our clients across the world.

Job Profile Summary

The Underwriting Transformation Lead will play a key role in establishing, governing and managing change delivery for a highly strategic area of the Chaucer business that spans Underwriting, Distribution, Pricing and Exposure Management functions. They will leverage deep experience of the London insurance and reinsurance market to provide a critical interlock between the business and the Transformation Office, overseeing a portfolio change that is critical to the delivery of Chaucer’s long-term strategic business goals.

Job Description

• Supports business teams to translate strategic ambition into clearly defined change projects and programmes.
• Ensures the portfolio and roadmap accurately reflects the change and transformation requirements of their respective area of the business and that they enable delivery of business specific and Chaucer wide strategy through realisation of benefits and value.
• Ensures initiatives are prioritised in line with requirements of the strategy using the defined prioritisation methodology.
• Ensures the appropriate tools, templates and approval steps are taken to define Change Briefs and Business Cases.
• Ensures Business Cases accurately reflect the needs of the business and that change initiatives are appropriately sized and valued.
• Ensures the appropriate business stakeholders are informed of and provide input to initiative shaping and design.
• Takes responsibility of programme management for selected initiatives within a specific portfolio, as agreed with Transformation leadership.
• Where taking on programme management responsibilities, oversees and drives delivery for appointed teams, working with Business, Transformation and Technology stakeholders to mobilise relevant resources to delivery programme goals.
• Manages programme plans and milestones, co-ordinating and reporting on status, including risk, issues and dependencies.

Business interlock

• Builds a deep understanding of the business strategy, priorities and performance to help provide strategic support and advice to shape change requirements and appropriately prioritise across the portfolio.
• Establishes and maintains strong partnership with their respective business area and associated leadership team.
• Actively challenges business leads to ensure they are providing the right level of strategic oversight and input to change delivery and upholding their responsibilities as business owners.
• Attends and contributes to relevant leadership meetings, forums and reporting.
• Creates effective delivery partnerships with Technology, COO and corporate functions.
• Oversees the selection, prioritization, and management of projects and programmes within the portfolio to ensure they deliver value.
• Ensures interdependencies between initiatives within and across portfolios are identified, understood and appropriately managed.
• Works in partnership with other Portfolio Leads to review and prioritise initiatives in line with Chaucer’s broader strategic plans.
• Maintains view of all resources deployed to and involved with delivery of initiatives within portfolio.
• Supports resource deployment decisions by building view of where critical skills exist across the business.
• Promotes a culture of continuous improvement by identifying lessons learned and best practices to enhance portfolio management processes.
• Chairs Portfolio Steering group for their respective area of the business, reviewing portfolio health, progress, key risks, issues and dependencies.
• Identifies potential risks within the portfolio and works with business and change resources to develop mitigation plans for these.
• Regularly reviews risks, fund allocation, and benefits realisation. Determines where escalation to executive review forums is required.

Skills and Competencies

• Specialty market background: deep, proven Underwriting and Pricing experience and knowledge within the London insurance and reinsurance market.
• Strategic Thinking – Ability to shape long‑term direction and align initiatives with organisational goals.
• Portfolio Management – Proven expertise in overseeing complex change portfolios with high‑level governance and prioritisation.
• Change Leadership – A good understanding of the change lifecycle, with emphasis on governance (high), reporting (mid), excellence (mid), and delivery (developing).
• Project & Change Management – Skilled in managing transformation initiatives from planning through execution.
• Stakeholder Engagement – Demonstrated ability to build trusted relationships and influence across diverse stakeholder groups.
• Problem Solving & Analytical Skills – Adept at diagnosing issues, interpreting data, and developing actionable insights.
• Financial Planning & Analysis – Experience in budgeting, forecasting, and evaluating financial impact of strategic decisions.
• Business & Commercial Acumen – Deep understanding of business operations and financial drivers, with the ability to translate strategy into results.
• Reporting & Insight Generation – Ability to produce clear, actionable reports that support decision‑making and performance tracking.

Why Join Chaucer?

Chaucer is a leading global insurer operating in both Lloyd’s and company markets, helping industries worldwide manage risk from nuclear, shipping, manufacturing, and property. Headquartered in London, with offices in Copenhagen, Bermuda, Sydney, Ireland, Miami, Dubai, and Singapore, we are close to our clients wherever they are. We have shown strong financial success with our Gross Written Premiums growing from $1.4bn in 2019 to $3.5bn in 2024. Backed by strong teams, platforms, and client relationships, Chaucer is poised for continued success.

We offer:

• A flexible office hybrid work model that supports individual and team needs.
• A diverse, inclusive culture that values people for who they are.
• Extensive, non‑contributory benefits, including medical, life, and pension cover, flexible holidays, and wellbeing support.