Assistant General Counsel – Insurance Regulatory & Corporate

Assistant General Counsel – Insurance & Regulatory

Location: Canada, Toronto – Ontario

Industry: Specialty Insurance / MGA

Experience: 10+ Years

The Opportunity

Oliver James is partnering with a leading international specialty insurance organization to appoint an Assistant General Counsel to lead its Canadian legal and compliance function.

This is an exciting opportunity for an experienced insurance lawyer to take ownership of a broad legal and regulatory portfolio, playing a pivotal role in shaping the legal and compliance infrastructure of a growing Canadian business.

Reporting into senior international legal leadership and working closely with the Canadian executive team, the successful candidate will serve as the primary legal and regulatory adviser for Canadian operations, providing strategic, commercially focused guidance across insurance regulation, licensing, corporate governance, commercial matters and business operations.

The position offers significant visibility, autonomy and the opportunity to influence business strategy while supporting continued growth in the Canadian specialty insurance market.

Key Responsibilities

• Legal & Compliance Leadership: Lead the Canadian legal and compliance function, providing strategic legal advice to senior executives and supporting the development of robust governance, risk management and compliance frameworks.
• Insurance Regulation & Licensing: Oversee the development and ongoing management of Canadian insurance licensing frameworks, including corporate and individual licensing, renewals, regulatory filings and engagement with provincial regulators.
• Regulatory Advisory: Advise on federal and provincial insurance legislation, regulatory compliance, delegated authority arrangements, privacy requirements, emerging AI regulation and relevant employment matters.
• Commercial & Corporate Legal: Review, draft and negotiate a broad range of commercial agreements, including supplier contracts, broker agreements, binding authority agreements, claims handling agreements and other strategic arrangements.
• Regulatory Engagement: Act as a key legal contact for regulatory authorities, oversee regulatory reporting obligations and translate legislative developments into practical business guidance.
• Cross-Functional Partnership: Collaborate closely with underwriting, claims, operations, compliance and executive leadership to ensure legal and regulatory considerations are embedded into commercial decision-making.
• Strategic Projects: Provide legal support on corporate transactions, M&A activity, portfolio acquisitions, cross-border initiatives and entity-level disputes.
• Governance & Risk: Work alongside international legal and compliance colleagues to implement appropriate policies, procedures, controls and escalation frameworks across Canadian operations.
  
  

About You

We are seeking a commercially minded, experienced Canadian insurance lawyer who combines strong technical regulatory expertise with the ability to operate as a trusted adviser to senior leadership.

The Ideal Candidate Will Bring

• Qualification to practise law in Canada, with 10+ years of relevant legal experience.
• Significant in-house legal experience within the Canadian insurance industry.
• Deep knowledge of Canadian federal and provincial insurance regulation, licensing requirements and compliance obligations.
• Strong understanding of Managing General Agents (MGAs), delegated authority arrangements and specialty insurance operations.
• Demonstrated experience overseeing corporate and individual insurance licensing frameworks.
• Previous experience leading or managing legal and compliance professionals.
• Strong commercial contracting, corporate advisory and regulatory engagement experience.
• The confidence to advise executive leadership and communicate effectively with Board-level stakeholders.
• Excellent judgement, communication and stakeholder management skills.
• Fluency in English; business-level French would be a distinct advantage.
  
  

Why Consider This Opportunity?

This position offers an exceptional opportunity to step into a senior legal leadership role within an established international specialty insurance business experiencing continued growth and development.

Key Highlights Include

• Leadership & Ownership: Take responsibility for the Canadian legal and compliance function, with the autonomy to shape regulatory strategy and internal frameworks.
• Executive Exposure: Work directly with senior Canadian leadership and international legal executives, influencing important commercial and strategic decisions.
• Broad Legal Remit: Enjoy a varied portfolio spanning insurance regulation, corporate and commercial legal matters, governance, licensing and strategic transactions.
• International Collaboration: Partner with experienced legal and business leaders across multiple jurisdictions.
• Strategic Impact: Play a central role in supporting the development and long-term success of a growing specialty insurance platform.
  
  

Interested in Learning More?

If you are an experienced Canadian insurance lawyer looking for an opportunity to combine technical regulatory expertise, commercial advisory responsibilities and senior leadership, we would welcome a confidential conversation.

Apply today or contact Oliver James for a confidential discussion about this opportunity.

We welcome applications from candidates with diverse professional backgrounds who meet the core requirements of the position.

Apply Now