Shape Canadian legal and compliance infrastructure in Toronto, using insurance licensing expertise and commercial judgement across a specialty insurance business.

This Assistant General Counsel position carries broad responsibility for Canadian legal, regulatory, and compliance matters. You will advise senior leadership on insurance legislation, licensing, privacy, AI regulation, employment matters, governance, and risk. The organization also values experience with MGAs, delegated authority, and specialty insurance operations.

Key Responsibilities

Develop governance, risk management, and compliance frameworks

Oversee regulatory filings, renewals, and provincial engagement

Advise on privacy and emerging AI regulation

Support underwriting, claims, operations,



and compliance teams

Implement policies, controls, and escalation frameworks

Requirements

Canadian legal qualification with 10+ years’ experience

In-house experience within the Canadian insurance industry

Experience overseeing insurance licensing frameworks

Experience leading legal and compliance professionals

Excellent judgement, communication, and stakeholder management skills

Use Canadian insurance law, compliance leadership, and stakeholder management skills to strengthen operations for this specialty insurance organization.

📌 Canadian Insurance Legal Compliance Counsel (Winnipeg)
🏢 Oliver James Group
📍 Winnipeg