Complex Loss Manager, Technical Specialist

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🔥 41 minutes ago

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Square One Insurance Services

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2011

🛡️ Insurance

👥 B2C

Insurance • B2C

Square One Insurance Services is a Canadian, digital-first insurer that sells personalized home, tenant and car insurance directly to consumers through an online platform and mobile app. Customers can get quotes, buy policies, manage accounts and submit claims online; the company emphasizes transparency, fast claims handling (states it pays over 90% of claims), guaranteed building replacement coverage, and flexible monthly or annual payments. Home and other personal lines are underwritten by The Mutual Fire Insurance Company of British Columbia, car insurance (available in Ontario and Quebec) is underwritten by Zurich, and legal protection by HDI. Square One operates across multiple Canadian provinces (including BC, AB, SK, MB, ON and QC) and markets primarily to retail consumers.

📋 Description

• You are a "technician’s technician" who stays ahead of industry trends. • Lead the professional development of adjusters & Examiners through technical workshops, desk-side mentoring, file reviews and the creation of advanced training curricula. • Provide expert oversight, strategy, and settlement authority for large-scale property losses and liability losses. • Expertly utilize and advocate for AI tools to perform rapid legal/technical research, summarize voluminous documentation, and generate training materials that optimize departmental learning. • Execute calibration exercises to ensure technical accuracy and the consistent application of best practices across the team. • Develop and deliver training workshops, using AI-simulated scenarios, where possible, to help adjusters practice negotiation and conflict management in a "sandbox" environment. • Participate in the Coverage Committee and senior leadership meetings to shape departmental policy. • Maintain your professional licenses and industry knowledge, with a specific focus on how emerging Insurtech affects liability and property valuation. • Train claims staff to treat losses not as files, but as critical incidents, bringing empathy and high-level crisis management to policyholders. • Mentor adjusters in the art of relationship building and de-escalating volatile disputes with claimants and legal counsel. • Responsible for maintaining the integrity of our workflow by defining exactly where the machine stops and the human expert begins. • Update and maintain technical documentation, the claims manual and all claim' handbooks.

🎯 Requirements

• Must hold a CIP (Chartered Insurance Professional) or FCIP (Fellow Chartered Insurance Professional) designation or possess an equivalent level of advanced formal insurance education or degree. • Extensive experience in handling complex residential property and liability files with a deep understanding of policy wordings and tort law. • At least 15 years of personal lines home insurance claims adjusting experience. • At least 5 years of management experience within the same field. • Prior experience providing claims training/workshops/coaching. • At least 1 year of tenure with a recent employer. • Must be fearless and curious in researching, adopting and teaching AI technologies to drive efficiency in research, productivity and claims analysis. • Exceptional ability to distill complex technical concepts into clear, actionable guidance for adjusters, stakeholders, and legal counsel.

🏖️ Benefits

• An annual salary range of $ $110,000 to $125,000 • Participation in the profit share program. • Performance bonus plan • 4-weeks of vacation to start and an additional week after only 3 years. • Full MSP coverage for you and your family. • Flexible medical, dental, vision and extended health care coverage. • Short and long-term disability coverage. • In-house and external training paid by Square One. • Work setup: in-office, hybrid or remote.