Senior Complex Claims Director, Casualty

Senior Complex Claims Director, CasualtyToronto, ON | North America
Salary Range: 160,000 CAD To 180,000 CAD
Who We Are:A strategic and trusted insurance partner, Berkshire Hathaway Specialty Insurance (BHSI), provides a broad range of commercial property, casualty and specialty insurance coverages and outstanding service to customers and brokers around the world. Part of Berkshire Hathaway's insurance operations, we bring our solutions to market with our stellar brand name, top-rated balance sheet, and the expertise of our global team of professionals, who exude excellent capabilities and strong character.
We are a values-based organization where respect, integrity, excellence, collaboration, and passion define who we are and how we do business. We value diversity of backgrounds, experience, and perspectives and strive to foster an inclusive environment that enables all our team members to bring their best selves to work. We are one team committed to building a culture where every teammate has the opportunity to contribute and be recognized. Want to be part of the team building the finest property, casualty and specialty lines insurance company in the world?
Berkshire Hathaway Specialty Insurance (BHSI) is seeking a Senior Complex Claims Director, Casualty Lines, to join our Claims team in Toronto. This role independently manages a diverse portfolio of complex primary and excess Casualty claims, applying deep expertise in claims analysis, coverage interpretation, negotiation, litigation strategy, and stakeholder management.
The Senior Complex Claims Director will drive timely, fair, and strategic claim resolutions while partnering with insureds, brokers, counsel, underwriters, and senior leadership. The role offers the opportunity to shape outcomes on high-impact claims while contributing to BHSI's reputation for technical excellence and exceptional customer service.
Duties & Responsibilities:
Independently manage complex Casualty claims from first notice of loss through final resolution.
Evaluate coverage, liability, damages, litigation exposure, and financial risk to establish and adjust claim strategy.
Develop and execute proactive resolution plans that balance customer needs, policy obligations, and business objectives.
Analyze policy language, apply contract interpretation principles, and make well-supported coverage determinations.
Draft clear and concise coverage position letters, claim recommendations, reports, and other claim-related communications.
Partner with defense counsel to develop litigation strategy, assess risk, manage legal activity, and pursue favorable outcomes.
Lead and participate in mediations, settlement negotiations, and dispute-resolution discussions.
Establish, monitor, and adjust reserves based on evolving facts, damages, and exposure analyses.
Build trusted relationships with insureds, brokers, customers, counsel, and other external stakeholders through responsive and professional claim handling.
Prepare and present recommendations to management regarding significant claim developments, strategy, exposure, and trends.
Qualifications, Skills and Experience:Qualifications:
15+ years of insurance industry experience, including at least 5 years in insurance claims, coverage litigation, defense litigation, or a related field.
University degree required;
Juris Doctor (JD) preferred.
Demonstrated experience handling General Liability, Products Liability, Construction/Wrap-Up Liability, Pollution, and Professional Liability claims.
Experience participating in mediations, settlement negotiations, and litigation management.
Strong organizational and time-management skills, with the ability to manage multiple complex matters simultaneously.
Key Skills:Complex Claims Management
Independently manages high-severity and technically complex Casualty claims across the full claim lifecycle.
Integrates coverage, liability, damages, litigation, and financial exposure into a clear claim strategy.
Maintains disciplined reserves and adapts plans as facts and exposures evolve.
Coverage Analysis and Technical Judgment
Interprets policy language and applies coverage provisions to complex claim scenarios.
Identifies material issues, evaluates competing information, and makes timely, well-reasoned decisions.
Translates complex coverage and legal concepts into practical recommendations and clear communications.
Negotiation and Resolution
Develops pragmatic resolution strategies and negotiates effectively in high-stakes situations.
Works productively with counsel and other stakeholders during mediations, settlements, disputes, and litigation.
Balances customer needs, contractual obligations, risk, and business objectives without compromising claim-handling standards.
Communication and Influence
Produces concise, accurate, and well-supported coverage letters, reports, and executive-level recommendations.
Builds credibility with insureds, brokers, counsel, underwriters, and senior leaders.
Influences outcomes through sound judgment, preparation, collaboration, and clear communication.
Customer and Business Focus
Delivers responsive, professional service while maintaining technical rigor and consistent claim practices.
Prioritizes effectively and manages multiple complex matters in a fast-paced environment.
Shares claim insights that strengthen decision-making, customer relationships, and business outcomes.
BHSI Offers:
A competitive package and exciting growth opportunities for career-oriented teammates.
A dynamic, action oriented, and thoughtful environment centered on always doing the right thing for our customers, teammates, and our other stakeholders.
A purposely non-bureaucratic organization that embraces simplicity over complexity and emphasizes individual excellence in a team framework.
Benefits that support your life and well-being, which include:Comprehensive Health, Dental and Vision benefits
Disability Insurance (both short-term and long-term)
Life Insurance
Accidental Death & Dismemberment Insurance
Critical Illness Insurance
Employee Assistance Program
Defined Contribution Pension Plan with Company Match
Generous holiday and Paid Time Off
Tuition Reimbursement
Paid Parental Leave
The base salary range for this position in Toronto is $160,000 - $180,000 CAD, along with annual bonus eligibility. Total compensation for a candidate is determined by their relevant skills, location, and experience. We value our teammates – both their capabilities and character – as demonstrated by our amazing culture.
NOTE: Compensation will be commensurate with experience. This job description is not intended to be all-inclusive. Team Member may perform other related duties as negotiated to meet the ongoing needs of the organization.
BHSI complies with Ontario's Accessibility for Ontarians with Disabilities Act (AODA) and has a process in place that provides accommodations for job applicants and teammates with disabilities (upon request).
We do not employ AI or automated tools to filter, assess, or select candidates
This posting is for an existing vacancy within the organization.
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