Complex Claims Director, Specialty & Financial Lines

Kibbi Technologies Inc.; Toronto; Hybrid; CAD 130,000 - 180,000; Full time

Benefits offered by this job

Company share ownership

Pension and RRSP contributions

Paid volunteer days

Tuition assistance

Incentive programs

Job summary

Definity in Canada is seeking a Complex Claim Director (lawyer) to lead coverage analyses, investigations, and dispositions for moderate to high-severity financial lines claims, collaborating with underwriting and claim teams. You will draft complex documents, negotiate settlements, manage outside counsel, and provide legal guidance to underwriters.

The role requires JD, provincial licensure, and 3–4+ years of experience; bilingual English/French preferred.

Qualifications

• Bachelor’s degree in law (JD/LLB) and licensed to practice in the province.
• Minimum 3–4+ years as lawyer or claims handling; 4+ preferred.
• Financial Lines experience in cyber, D&O, and E&O is ideal.
• Strong negotiation and document drafting skills.
• Proficient in MS Office; able to convey legal concepts to stakeholders.

Responsibilities

• Conduct coverage analyses and investigations for complex claims.
• Prepare management reports on loss exposure and claim strategy.
• Coordinate recovery opportunities and manage outside counsel payments.
• Answer underwriting questions with legal analyses to support decisions.
• Draft coverage letters, releases, settlements, and other transactional documents.
• Draft reference materials on laws impacting underwriting and claims.

Skills

Bilingual English/French

Negotiation

Legal research

Claims handling

Drafting & communication

MS Office

Education

JD / LLB (licensed in province)

Tools

MS Office

Job description

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. Our ambition is to be one of Canada’s leading and most innovative property and casualty insurers. We can’t do that without our people, so we embrace and encourage a culture that’s collaborative, ambitious, rewarding, and empowering.

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. Bring your true self and be a part of our journey. It’s better here.

The Opportunity

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.

What to Expect

• 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.
• Identify and coordinate all recovery opportunities and efforts.
• 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.

What you Bring

• Bachelor’s degree and a Juris Doctor (LLB/JD) are required.
• Must be a duly qualified practitioner of law in the province of employment.
• 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; 4+ years of experience is preferred.
• Prior Financial Lines insurance experience in privacy/cyber, directors' and officers' liability, and errors and omissions liability is ideal.
• 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.
• Demonstrated ability to work through conflict and resolve issues with a professional demeanor.
• Proficiency in MS Office and strong overall technical aptitude.

Salary Range: $130,000 - $180,000

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.

What’s in it for you?

• Hybrid work schedule for most roles
• Company share ownership program
• 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
• Paid volunteer days and company matching on charitable donations
• Educational resources, tuition assistance, and paid time off to study for exams
• Focus on inclusion with employee groups, support for gender affirmation surgery, access to BIPOC counsellors, access to programs for working parents
• Wellness and recognition programs
• Discounts on products and services

Go ahead and expect a lot — you deserve it.

It’s better here — but don’t take our word for it. 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. If you require accommodation at any time during the recruitment process, please let us know by contacting [e-mail].

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.

Background checks

This role requires successful clearance of background checks (including criminal checks and leadership references).