Senior Corporate Legal Counsel

With every job, there’s always the question of “why”. Why join a company? Why be part of their mission? Here, the why is easy. It’s because at some point, we’ve all needed someone there for us.

At the OTIP Group of Companies (OGC), we believe that something special happens when employees feel valued for the work they do, supported as the people they are, and included in the very fabric of the organization: they bring their best to work every day. And that's why we mean it when we say we put our people at the centre of everything we do.

Join us as we grow our way into a future that reimagines what it means to deliver meaningful benefits support and service.

What You’ll Do:

Reporting to the Chief Operating Officer & Chief Financial Officer, you’ll be a key member of the corporate legal team providing practical advice to leadership and internal business partners on a wide range of risks. You will be relied upon to solve complex legal issues and proactively manage risks associated with third-party contracts, compliance, and regulatory requirements.

The core parts of your role will be to:

• Prepare, analyze and review a variety of legal agreements, including NDAs, MSAs, vendor agreements, lease agreements and service contracts, etc., ensuring compliance with legal standards and company policies.
• Negotiate contract terms with partners, vendors and service providers to identify and mitigate potential risks and achieve favourable outcomes, protecting OGC’s interests.
• Liaise with cross-functional teams such as vendor management, third-party risk management and privacy, to support contract lifecycle management.
• Conduct legal research and prepare summaries or guidance on insurance regulations, licensing, and compliance issues across Canadian jurisdictions that impact OGC, advising on risks and the most appropriate response or action.
• Monitor and maintain knowledge of regulatory requirements related to OGC, such as individual insurance products, group health benefits, employment law, AI, and privacy law and advise on regulatory requirements and developments. Communicate important legal updates and processes across teams in clear and concise language.
• Conduct legal review of internal policies and business initiatives to ensure regulatory compliance.
• Oversee corporate law compliance and governance matters, providing expert legal advice and risk management guidance to senior leadership and the Board of Trustees.
• Work collaboratively with business partners and internal stakeholders to provide practical, risk-based legal advice on a wide range of matters.
• Oversee the legal process, including management of outside counsel as necessary when external legal expertise is required, ensuring high-quality service and cost-effectiveness.
• Contribute to internal knowledge resources and support continuous improvement of legal workflows.
• Manage, coach and develop members of the legal services team.

Let’s Talk

About You:

This is the unique blend of skills and experience we would love to see in an ideal candidate:

• A JD or LLB from an accredited law school and a member in good standing with the Law Society of Ontario.
• Minimum 5-10 years’ experience as in-house counsel. Experience in a corporate financial services and/or insurance company would be considered an asset.
• Proven experience in contract lifecycle management, drafting, review and negotiation.
• Ability to manage tight deadlines and prioritize work effectively by taking a risk-based approach.
• Strong communication skills and ability to communicate legal advice clearly to non-legal stakeholders.
• Ability to engage and influence others with confidence, build solid working relationships and work as a team player.
• Strong attention to detail, organizational skills and commitment to accuracy with experience addressing multiple projects.
• Intermediate knowledge of Microsoft Office Suite applications.
• The ability to communicate in French is considered an asset.

We also consider your potential. If you know you have what it takes to do the job, but your experience doesn’t exactly match the qualifications above, we encourage you to apply and provide us with more details about…