Senior Complex Claims Examiner

Crawford & Company • Toronto, IA

6d • Remote

About The Position

This is a senior technical claims role responsible for handling and examining large, complex losses across casualty, professional liability, medical malpractice, construction liability, and cyber lines. This is a remote position. The role manages active litigation files, directs defence and coverage counsel, develops litigation strategy, and provides technical guidance to examiners and adjusters on complex coverage issues, coverage correspondence, and claim resolution strategy. This position does not supervise staff; however, it is expected to serve as a senior resource and escalation point for complex litigation and coverage matters.

Requirements

• Bachelor's Degree in Insurance, Risk Management, Business Administration, Law, or a related field.
• Equivalent combinations of education, specialized training, and relevant industry certifications will be considered.
• Extensive claims handling experience, including exposure to litigation management and complex casualty claims.
• Demonstrated expertise in one or more specialty lines, including: Professional Liability, Medical Malpractice, Construction Liability, Cyber Liability
• Proven experience managing complex, high-exposure claims from investigation through resolution.
• Experience directing defense counsel and coverage counsel, reviewing legal opinions, and developing litigation strategies.
• Strong background in managing legal spend, claim reserves, settlement negotiations, and risk assessment.
• Ability to analyze coverage issues and make sound liability and claim resolution decisions.
• Experience collaborating with internal stakeholders, brokers, underwriters, and external legal partners.
• Demonstrated ability to effectively prioritize and manage multiple complex claims in a fast-paced environment while maintaining regulatory and contractual compliance.

Nice To Haves

• Experience working with Lloyd's market business, delegated authority arrangements, Managing General Agents (MGAs), insurers, brokers, or specialty market clients preferred.

Responsibilities

• Handle and examine large, complex, and high-exposure claims across casualty, professional liability, medical malpractice, construction liability, and cyber lines of business.
• Review claim facts, policy wording, coverage positions, liability, damages, reserves, litigation status, and resolution options.
• Identify coverage, defence, indemnity, quantum, and reputational issues requiring escalation or client consultation.
• Manage litigated files from assignment through resolution, including strategy, budgets, discovery, mediation, arbitration, pre-trial, trial preparation, settlement, and closing documentation.
• Select, assign, instruct, and direct defense and coverage counsel, ensuring legal strategy is aligned with policy obligations, client expectations, and claim resolution goals.
• Review pleadings, legal opinions, defence plans, coverage opinions, mediation briefs, settlement recommendations, and litigation budgets.
• Monitor legal spend, counsel performance, reporting quality, and compliance with client guidelines.
• Prepare, review, and support complex coverage analyses, reservation of rights letters, coverage position letters, denial letters, and related coverage correspondence.
• Assist examiners and adjusters with complex coverage questions, strategic file direction, litigation risk assessment, and client reporting.
• Promote consistency, clarity, and technical quality in coverage communications and litigation management practices.
• Direct further investigation where required and ensure relevant information is obtained, assessed, and documented.
• Evaluate liability, causation, damages, coverage, indemnity exposure, litigation risk, and settlement value.
• Develop and maintain disposition plans, reserve recommendations, and resolution strategies that reflect claim facts, policy wording, legal advice, and client requirements.
• Negotiate or direct negotiation of settlements through counsel, brokers, insureds, claimants, and other stakeholders as appropriate.
• Maintain accurate claim file documentation, diary management, bordereaux entries, client systems, and internal claim systems.
• Provide timely, clear, and technically sound reports to clients, Lloyd's market participants, brokers, insurers, and internal stakeholders.
• Ensure compliance with Lloyd's market expectations, client programs, service standards, regulatory requirements, privacy obligations, and internal procedures.
• Review and approve legal accounts, time records, expenses, and related claim costs in accordance with authority levels and client guidelines.
• Interact professionally with clients, Lloyd's market stakeholders, brokers, insureds, claimants, counsel, experts, and internal claim teams.
• Respond to complex inquiries, explain claim strategy and coverage positions, and support strong client relationships through timely communication and technical credibility.
• Participate in claim reviews, market meetings, mediations, arbitrations, examinations for discovery, pre-trial conferences, and other litigation or dispute resolution events as required.
• Upholds the Crawford Code of Conduct at all times.
• Participates in special projects or performs other duties as requested.

Benefits

• Performance-based pay and incentive plans that recognize excellence.
• Retirement savings options, including pension, group RRSP, TFSA, and an Employee Stock Purchase Plan.
• Benefits that support your financial, physical, and mental well-being.
• Flexible work options that support work-life balance, including shortened work weeks, phased retirement, and generous time away.
• Training, development, and scholarship programs that support continuous learning, career growth, and education at various career stages.
• Additional support, including home office allowance, employee referral bonuses, relocation support where applicable, and corporate discounts.
• Paid volunteer time and sustainability initiatives that help give back to the communities where we live and work.
• A culture built on respect, collaboration, inclusion, and entrepreneurial spirit.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior