Are you looking to reignite your career within a global organisation known for its exceptional culture and genuine care for its people? If so, Chaucer would be delighted to hear from you.

At Chaucer, we recognise the strength that comes from diverse experiences, perspectives and career journeys, and provide an extensive range of family friendly policies to help our people achieve this. As proud participants in the Insurance Cross‑Company Returners Programme, we’re opening our doors to talented professionals ready to return to the industry and make their next chapter their best yet. Opportunities are available in London for those with experience in:

Underwriting
Underwriting Operations
Legal and Regulatory

About Chaucer

Chaucer is a leading specialty (re)insurance group with a global footprint and a reputation for doing things the right way. With our Lloyd’s syndicate at the heart of our business, and additional platforms across international markets, we deliver smart, tailored solutions to clients around the world.

But what truly sets us apart is our people. We build deep, lasting relationships with colleagues, brokers and clients, and we foster an environment where everyone can bring their whole selves to work. We listen to every voice, value every perspective, and make decisions based on merit. This inclusive culture fuels innovation, strengthens our customer experience, and supports our commitment to the communities and markets we serve.

About the Programme

A professionally paid 6‑month placement running from May to November 2026
A likelihood of a permanent role on successful completion (subject to performance and business requirements)
An internal mentor and a dedicated buddy to support your transition back into work
Access to Career Returners’ specialist coaching throughout the programme
A ready‑made peer group of fellow returners across the insurance market
Flexible, hybrid working arrangements available

Opportunities on the Programme

Underwriting

Our underwriting teams work at the heart of our business, partnering closely with global and regional brokers to craft specialist (re)insurance solutions for individuals, businesses and professionals across a wide range of sectors. It’s a role that blends technical expertise with sound judgement and commercial awareness. As part of the team, you’ll play an active role in shaping policy terms, assessing and pricing risk, and helping to build and maintain a balanced, profitable portfolio. You’ll contribute to decisions that directly influence our client relationships, our market position and our long‑term performance.

This is a collaborative environment where underwriters work alongside colleagues in Claims, Wordings, Actuarial and Operations to deliver the right outcomes for clients and brokers. You’ll have the opportunity to deepen your market knowledge, develop trusted relationships and gain exposure to the full lifecycle of underwriting within the Lloyd’s market.

We’re looking for returners who bring skills in underwriting, relationship building, portfolio management and data analysis - and who are curious, commercially minded and ready to re‑engage with a fast‑moving, intellectually stimulating discipline.

Underwriting Operations

This role is well suited to returners with broad London Market experience who are looking to apply their knowledge in a role that strengthens the effectiveness of Chaucer’s business operations.

You will support key operational areas, including Operational Resilience, Credit Control and Delegated Underwriting. Your contribution will help refine processes, enhance controls and improve the efficiency and consistency of our underwriting operations. This work plays an important part in ensuring Chaucer continues to meet the high standards expected across the Lloyd’s market and beyond.

The role offers significant variety and cross‑functional exposure. You will work across multiple projects, collaborating with project managers, underwriting teams and wider business stakeholders to deliver well‑executed, meaningful change. Activities may include supporting governance activity, improving workflow design, embedding new operational practices and contributing to initiatives that strengthen the way Chaucer operates.

This opportunity is ideal for individuals who enjoy problem‑solving, building meaningful working relationships and bringing structure and clarity to complex environments. It provides a valuable route back into the market for those seeking to re‑establish their career within a dynamic and collaborative team.

Legal & Regulatory

Our Legal & Regulatory teams play a central role in safeguarding the business, supporting good governance and ensuring we meet the high standards expected across the Lloyd’s market. These teams work closely with colleagues across Underwriting, Claims, Operations and the wider Group to provide clear, practical guidance that enables the business to operate with confidence and integrity.

We’re keen to hear from returners with experience in any of the following areas: Legal, Compliance, Wordings or Company Secretarial.

Depending on your background, you may contribute to:

Supporting regulatory compliance and horizon‑scanning
Drafting, reviewing and maintaining policy wordings
Advising on governance matters and supporting Board and committee activity
Providing legal insight on contracts, disputes or commercial matters
Strengthening frameworks that underpin conduct, culture and risk management

If you’re someone who brings sound judgement, analytical skills and a collaborative approach, this could be an excellent route back into the market.

Eligibility Criteria

You must have the right to work in the UK (sponsorship is not available)
You must have taken a career break of 18 months or more by May 2026
(This may include small‑scale or occasional work, or a complete break from paid employment)

How to Apply

To apply to the programme, please submit your CV by following the link below, and specifying which opportunity is of interest. Please ensure your career break is clearly highlighted on your CV.

If you have any questions on the programme, please contact: recruitment@chaucergroup.com

The closing date for applications is 2 March 2026.

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.

Our headquarters are in London, and we have international offices in Bermuda, Copenhagen, Dubai and Singapore to be closer to our clients across the world. To learn more about us please visit our website.

Chaucer is committed to diversity, actively values difference and respects people regardless of the protected characteristics which are outlined in the Equality Act 2010 (UK legislation) as a result of the Equal Treatment Directive 2006 (EU legislation).

A diverse workforce and an inclusive workplace are core to our success as a business and integral to our winning strategy and culture. We recruit from the widest available pool of talent, and our hiring, assessment and selection process is fair, free from bias and one which ensures we select the right person for the job, based on merit. We are committed to promoting a culture that actively values difference, and recognises that everyone has the right to be treated with dignity and respect throughout their employment.

We are open to considering flexible working arrangements for all roles and encourage you to outline your needs during the interview process.

Legal and Regulatory jobs

2026 Career Returnships Programme