Technology Delivery Manager (12 month FTC)

About us

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. To learn more about us please visit our website: www.chaucergroup.com

Role Summary

The Technology Delivery Manager is responsible for leading the end-to-end delivery of technology initiatives across their allocated portfolio, with a strong emphasis on finance transformation programmes and projects. The role blends deep technology delivery expertise with proven experience of delivering complex finance change, including finance systems modernisation, data, regulatory and operating model transformations.

Sitting within the Transformation organisation, this role is a key partner to Finance, Product Management and Technology teams. The postholder will be accountable for translating business and finance strategy into executable delivery plans, ensuring outcomes are delivered on time, within budget and to agreed quality standards, while embedding sustainable change into Business-as-Usual (BAU).

Key Accountabilities

Delivery & Execution

• Own the end-to-end delivery of complex technology programmes and projects, including finance transformation initiatives spanning systems, data, process and operating model change
• Deliver multi-year finance technology roadmaps aligned to business strategy, regulatory requirements and product priorities
• Ensure delivery plans are robust, realistic and actively managed, with clear milestones, dependencies and critical paths

Finance Transformation Focus

• Lead delivery of finance transformation initiatives such as finance system implementations or upgrades, data and reporting platforms, regulatory programmes (e.g. finance change driven by accounting or prudential regulation), and finance process automation
• Partner closely with Finance stakeholders to understand end-to-end finance processes, controls and reporting requirements
• Ensure technology solutions support finance outcomes including control, auditability, data quality, scalability and operational resilience
• Bridge the gap between Finance, Technology and wider business teams, ensuring shared understanding and clear ownership

Stakeholder & Business Partnership

• Act as a senior delivery partner to Finance leadership, Product Management and Technology leads
• Build strong, trusted relationships across Finance, Engineering, Architecture, Service Management, Change and QA functions
• Communicate progress, risks and issues clearly and proactively to senior stakeholders
• Support executive-level decision making through clear reporting, options analysis and delivery insight

Leadership & Ways of Working

• Provide strong delivery leadership, setting clear direction and expectations for delivery teams
• Champion modern delivery practices, including agile and hybrid delivery models, while working effectively within enterprise governance constraints
• Coach and mentor delivery managers, project managers and team members, building delivery capability and maturity
• Promote continuous improvement, learning and high standards of delivery excellence

Risk, Dependency & Vendor Management

• Identify, assess and actively manage delivery risks, dependencies and interlocks across complex change landscapes
• Develop and implement mitigation strategies to protect outcomes
• Manage third-party vendors and systems integrators, ensuring commercial value, delivery quality and contractual performance

Performance & Assurance

• Define and track delivery KPIs and outcomes, using data to drive transparency and continuous improvement
• Ensure effective quality, testing and assurance approaches are embedded across delivery
• Support internal audit, risk and regulatory engagement by providing clear evidence of delivery controls and outcomes

Skills, Experience & Competencies

Experience

• Proven experience in technology delivery management roles, delivering complex, enterprise-scale change
• Demonstrable track record of delivering finance transformation initiatives and programmes
• Experience working in regulated environments, ideally within financial services or insurance
• Strong background in managing cross-functional, matrix teams
• Experience working with senior Finance stakeholders and translating finance requirements into technology delivery

Core Skills

• Excellent delivery management, planning and execution capability
• Strong understanding of finance systems, data and control environments
• Highly effective stakeholder management and communication skills
• Commercially astute, with experience managing vendors and third-party delivery partners
• Strong analytical and problem-solving capability, able to operate at both strategic and detailed levels

Leadership & Behaviours

• Resilient, adaptable and comfortable leading delivery through change and uncertainty

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're 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 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.