Definity is the parent company to some of Canada’s most long-standing and innovative insurance brands, including Economical Insurance, Sonnet Insurance, Family Insurance Solutions, and Petline Insurance.

We offer a flexible, hybrid work experience where employees work from the office and virtually depending on the type of work they are doing and who they are working with.

The Complex Claim

Director is a lawyer responsible for managing claims under various policies, including cyber liability, directors’ and officers’ liability, employment practices liability, fidelity and crime, and other miscellaneous professional liability policies.The Complex Claim Director is responsible for conducting thorough coverage analyses, investigations, evaluations, and dispositions of claims to achieve superior customer service and results. This role effectively manages assigned Financial Lines claims of moderate severity or complexity while interacting and collaborating with claim and underwriting colleagues.

Conduct thorough coverage analysis, investigation, negotiation, and resolution for moderate to high-severity claims with moderate supervision.

Prepare reports for management that accurately reflect loss development, potential financial exposure, coverage issues, and claim strategies.

Retain, monitor, manage, and approve payments to outside counsel for routine litigation matters, actively using litigation management plans and budgets.

Answer legal questions from underwriters that impact underwriting decisions, combining legal research with knowledge gained from claim-handling experience.

Review and draft moderately complex documents, including coverage and reservation of rights letters, releases, and settlement agreements.

Negotiate settlements and resolutions, both directly and through counsel, using legal arguments relevant to liability, damages, and coverage.

Draft reference materials to help claim and underwriting colleagues understand laws impacting underwriting and claim decisions.





Bachelor’s degree and a Juris Doctor (LLB/JD) are required.

Bilingualism (English and French) is preferred, with strong verbal and written communication skills in both languages.

A minimum of 3 years of experience as a lawyer (in-house or private practice) or in claims handling is required; Strong negotiation skills and strategies for both litigation and non-litigation contexts.

Proficiency in drafting transactional documents and communicating legal advice effectively to various stakeholders.

Proficiency in MS Office and solid overall technical aptitude.

High degree of proficiency with English required to service customers, both internal to the company and external, across Canada.

Actual salary for the role may vary depending on work location of the successful candidate and other factors including but not limited to, skills, education, experience, working conditions and the local labour market.

We’re actively seeking diverse backgrounds and perspectives to help us make insurance better.

At Definity, inclusion, diversity, and equity aren’t just “nice to have” — they’re essential to our success.

Incentive Program - Eligible employees may participate in various incentive plans which are paid out at the discretion of the company and subject to individual and company performance.

Pension and savings programs, with company-matched RRSP contributions

Focus on inclusion with employee groups, support for gender affirmation surgery, access to BIPOC counsellors, access to programs for working parents

Definity was named by Great Place to Work® as one of the Best Workplaces™ in Canada for women, for youth, and for inclusion.

Our inclusive work environment welcomes diversity and supports accessibility. As part of Definity’s commitment to reconciliation, we acknowledge that our work, meetings, and travel take place on the lands now known as Canada, and recognize the enduring presence, wisdom, and stewardship of the First Nations, Métis, and Inuit peoples who have long cared for these lands.

📌 Complex Claims Director, Specialty & Financial Lines (Toronto)
🏢 Kibbi Technologies
📍 Toronto