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Toronto, Ontario, Canada
Remote only
Contract Lifecycle Management: Draft, review, and negotiate complex commercial agreements, including SaaS licenses, vendor contracts, and partnership/binder agreements with our insurance markets.
MGA & Underwriting Support: Support product development, underwriting authorities, and digital automation risks.
Regulatory Compliance & Governance: Ensure ongoing compliance with provincial insurance regulators (such as RIBO) across Canadian operating provinces. Assist the GC in preparing materials for the Board of Directors.
Claims & Litigation Support: Provide expert legal guidance to the internal Claims/Errors & Omissions (E&O) team on complex files, litigation matters, and risk mitigation strategies.
Privacy Program Leadership: Serve as the official enterprise authority on privacy, maintaining and evolving our data protection framework alongside the Information Security Officer (ISO) to ensure strict adherence to PIPEDA and provincial legislation.
Privacy Assessments: Develop, maintain, and oversee Privacy Impact Assessments (PIAs), with a specific focus on protecting an online, digital-first insurance platform.
Incident Response & Training: Lead the legal response team for data security incidents or privacy inquiries, managing breach notification assessments and transparent reporting. Develop and deliver ongoing compliance and privacy training for our 350+ staff members.
AI Governance & Tech Ethics: Collaborate closely with IT, software engineers, and data scientists to establish ethical and legal guardrails for AI implementation, machine learning initiatives, and AI-driven underwriting tools.
Compliant Disruption: Stay ahead of emerging Canadian tech regulations to ensure our "speed-to-quote" technology remains a competitive advantage while staying fully compliant.
Marketing Review: Partner with our high-growth marketing team to review digital, online, and traditional marketing initiatives, ensuring regulatory compliance for the company's largest budget component.
Support the GC/CECO in maintaining and evolving our corporate Ethics and Compliance program, ensuring our culture of integrity evolves with our growth.
Education & Bar Admission: Bachelor of Laws (LL.B.) or Juris Doctor (J.D.) degree; active member in good standing with a Canadian common law society (e.g., Law Society of Ontario).
Experience: 6 to 10+ years of post-call experience, ideally blending top-tier law firm training with in-house experience in property & casualty (P&C) insurance, fintech, or the broader financial services sector.
Industry & Tech Knowledge: Deep familiarity with the Canadian insurance regulatory landscape, digital brokerage models, and MGA structures. Comfort advising on digital technology, online platforms, and advanced tools like AI.
Privacy Credentials: Demonstrated expertise in data protection law; a professional privacy certification (e.g., CIPP/C) is highly preferred and considered a significant asset.
The "Startup-to-Scaleup" Mindset: Proven ability to navigate a corporate transition from a "build fast" startup environment to a highly regulated, "steady-state" corporate structure. Ability to formalize corporate governance without stifling innovation.
Corporate Diplomacy & Influence: Exceptional communication skills with the ability to translate complex legal risks into solution-oriented business advice for non-legal stakeholders. Possess the "corporate diplomacy" required to speak the entrepreneurial language of a tech startup while satisfying the rigorous reporting demands of a Fortune 500 parent company.
The Best of Both Worlds: Experience the entrepreneurial spirit and speed of a tech disruptor combined with the stability, backing, and resources of a global insurance giant.
Direct Impact: As the second lawyer in the organization, your work will directly shape our corporate processes, legal frameworks, and scaling trajectory.
At the Forefront of Innovation: We don't just use tech; we build it. You will face cutting-edge legal issues involving AI and digital automation in the evolving Insurtech space.
