Insurance Manager (Markham)

Company Description White Owl Family Office Group is a private investment organization specializing in real estate, private businesses, and public and private equity and debt instruments. With operations in both Canada and the United States, the company is strategic in its approach to investment opportunities. White Owl Family Office Group is committed to sustainable growth and maintaining long-term value for its stakeholders, making it an ideal place for professionals seeking to make an impact in the investment and financial sectors. Role Description The Insurance Specialist will play a key role in overseeing the organization’s insurance programs, including close coordination with the captive insurance structure. This role works extensively with the captive manager, actuaries, insurance brokers, and internal stakeholders to ensure appropriate coverage, comprehensive record maintenance, accurate data flow, effective claims financial management and reconciliation and governance across the traditional placement and captive portfolios. This is a hands-on, in-office role for a highly organized, strategic candidate with strong technical knowledge, attention to detail, excellent communication skills, and the ability to actively manage data, documentation, and day-to-day insurance activities. The ideal candidate has 7+ years of experience including insurance captives and commercial lines. Less experienced candidates who don't meet all qualifications may be considered for an "Insurance Specialist" role. Reports to: General Counsel, with a dotted line to the Chief Financial Officer Key Responsibilities 1. Insurance Program & Captive Coordination - Support oversight and ongoing management of the organization’s insurance captive, coordinating with the captive manager on operational, regulatory, and reporting requirements. - Serve as a liaison among the captive manager, actuaries, brokers, the Insurance & Claims Manager / Claims Department (claims handling), the General Counsel, and the CFO to ensure alignment and timely information flow. - Coordinate standardized insurance and claims financial inputs required for actuarial analyses and captive reporting (format, completeness, and timelines). - Maintain and track captive-related reporting deadlines and required deliverables, escalating timing or data risks early. 2. Annual Insurance Renewals & Broker Management - Coordinate the annual insurance renewal process for each direct investment company, including timelines, data requests, internal review, and broker/insurer submissions. - Work closely with insurance brokers to manage renewals, endorsements, and coverage reviews across commercial insurance policies. - Gather required underwriting and exposure data from business leaders using prescribed, standardized templates; review submissions for completeness and accuracy prior to broker and insurer review. - Maintain working knowledge of policy terms, limits, deductibles/SIR, key conditions, and exclusions to support internal issue-spotting; escalate material coverage structure recommendations and binding decisions to the General Counsel/CFO for approval. - Coordinate certificates of insurance and support confirmation of contract insurance requirements in collaboration with Legal and brokers (as applicable). - Track policy issuance and endorsement execution to ensure final policy documents and endorsements are received, reviewed for accuracy, and filed promptly. 3. Data, Records & Reporting - Maintain an accurate, up-to-date database of all insurance policies (commercial and personal lines), including policy documentation, insured entities/assets, key terms, and renewal dates. - Coordinate timely receipt of claims information from insurers/TPAs and portfolio companies in collaboration with the Insurance & Claims Manager / Claims Department. - Ensure consistency, accuracy, and completeness of policy documentation, claims financial records, and related datasets provided to actuaries and the captive manager. - Claims financial reconciliation: with support from Insurance & Claims Manager, responsible for end-to-end claims financial reconciliation across the portfolio (paid indemnity, ALAE/ULAE, reserves, deductibles/SIR, salvage/subrogation and other recoveries), ensuring consistency across insurer/TPA statements, captive reporting/bordereaux, and internal financial records. - Reconciled reporting pack: produce a recurring reconciled loss run / claims financial pack (monthly/quarterly) with variance commentary, aging, and actionable exceptions for the General Counsel, CFO, captive manager, and actuaries. - Captive/reinsurance interface: track and support captive/reinsurance financial flows where applicable (e.g., recoverables/cash calls) and respond to data requests for renewals/actuarial views using reconciled datasets. - Prepare clear and professional presentations, analyses, and summaries related to the insurance program for the General Counsel, CFO, executive team, and other senior stakeholders. 4. Cross-Functional Collaboration & Continuous Improvement - Serve as a central insurance resource for internal teams and portfolio company leadership, including guidance on insurance data requirements, documentation standards, and timelines. - Drive continuous improvement of insurance processes, templates, controls, and reporting cadence to improve quality, consistency, and timeliness across the portfolio. - Handle insurance and claims information with appropriate confidentiality and in accordance with internal governance requirements. Required Qualifications - Demonstrated experience in a hands-on insurance operations / insurance analyst / brokerage / carrier / TPA or comparable role with direct ownership of insurance and/or claims data, documentation, and recurring reporting deliverables. - Advanced, hands-on Excel capability (including building reconciliation models and working with large datasets); ability to independently produce accurate, audit-ready schedules and reporting. - Demonstrated experience performing multi-source financial reconciliations and variance/exceptions analysis (e.g., insurer/TPA statements to internal records), with robust data quality controls. - Working knowledge of commercial P&C; insurance concepts and policy terms (limits, deductibles/SIR, endorsements, exclusions) sufficient to support renewals, identify data gaps, and flag coverage/wording issues for escalation. - Strong quantitative and analytical skills, exceptional attention to detail, and the ability to manage work independently with minimal supervision while coordinating effectively with multiple stakeholders. Core Competencies - Hands-on, detail-oriented approach to work. - Solid, hands-on Excel and data management skills. - Strong analytical and problem-solving capabilities. - Clear and professional written and verbal communication. - Ability to manage multiple stakeholders, deadlines, and data sources. - Deadline-driven. Preferred Experience - Experience working with or alongside a premier insurance broker or in an large institutional corporate insurance program. - 7+ years in a hands-on insurance operations, insurance analyst, carrier, TPA, or risk/insurance support role with or alongside a premier insurance company or captive, with direct responsibility for data, documentation, and recurring reporting deliverables. - Demonstrated advanced Excel capability (e.g., complex formulas, Power Query, PivotTables, reconciliation workflows; VBA/macros an asset). - Experience building and maintaining recurring management reporting packs and/or dashboards (Power BI an asset), including variance analysis and exception tracking. - Experience performing financial reconciliations across multiple data sources (e.g., insurer/TPA statements, internal financial records), with strong data quality controls and auditability. - Claims financial literacy (paid loss, reserves, deductibles/SIR, recoveries; ALAE/ULAE concepts) and ability to translate claim financial activity into clear summary reporting. - Exposure to captive insurance programs and working with captive managers and actuaries; ability to prepare reconciled datasets for actuarial/reserving and renewal support. - Exposure to reinsurance data flows/recoverables and/or reinsurance reporting requirements. - Experience coordinating policy issuance, endorsements, and certificates of insurance (COIs), and maintaining an organized policy database and document control discipline. - Strategic understanding of underwriting principles and considerations. Credentials / Training (assets): - Canadian P&C; insurance designation (CIP or equivalent) or progress toward completion - Familiarity with claims expense/reserving concepts (e.g., ALAE/ULAE) - Demonstrated advanced Excel capability; Microsoft Office Specialist: Excel Expert or equivalent - Power BI competency; Microsoft Certified: Power BI Data Analyst Associate (PL‑300) or equivalent - Captive insurance education (e.g., Associate in Captive Insurance (ACI)) - Reinsurance education (e.g., Associate in Reinsurance (ARe)). - Risk management education (e.g. CRM or similar) Apply on Kit Job: kitjob.ca/job/2o398x