Legal Services Director

OLG • Toronto, ON

5d • CA$190,000 - CA$240,000 • Onsite

About The Position

We are ready to take this game to the next level and need a passionate Legal Services Director. This role will have responsibilities which have a high impact on all aspects of OLG’s business and operations and will play an important role in protecting the organization from ongoing and emerging legal and reputational risks.

Reporting to the Senior Managing Counsel, Legal Services, Corporate and Litigation, the Legal Services Director will expertly manage and oversee litigation and provide expert and strategic legal advice across the enterprise on various issues, including human resources, litigation, and privacy matters to advance OLG’s strategic goals.

Requirements

• Juris Doctor (JD) or Bachelor of Laws (LLB) degree.
• Member in good standing with the Law Society of Ontario.
• Minimum 8 years of progressively senior legal experience in litigation, gained through a law firm and/or in-house legal environment within a public or private sector organization.
• Experience providing legal advice and strategic counsel to senior leaders on complex legal, business, and regulatory matters.
• Experience conducting workplace investigations and advising on employment-related matters.
• Advanced advocacy, negotiation, and conflict resolution skills, with the ability to influence outcomes and provide sound legal advice on complex matters.
• Strong legal research, analysis, and drafting skills.
• Exceptional oral and written communication skills, with the ability to build consensus, negotiate effectively, and communicate complex legal concepts to diverse audiences.
• Demonstrated ability to manage complex legal files independently while applying strong problem-solving, strategic-thinking, and decision-making capabilities.
• Strong relationship management skills with the ability to establish credibility and maintain productive partnerships across the organization.
• Experience advising on employment-related matters and conducting workplace investigations.
• Strong knowledge of privacy legislation and regulatory requirements, including FIPPA and related privacy frameworks.
• Strategic mindset with the ability to navigate complex challenges and develop practical, business-focused solutions.
• Inclusive and collaborative work style that fosters strong relationships, teamwork, and engagement.
• Operates with integrity, transparency, and professionalism while maintaining the highest ethical standards.

Nice To Haves

• Experience interpreting and advising on privacy legislation, including the Freedom of Information and Protection of Privacy Act (FIPPA), is considered an asset.

Responsibilities

• Provide timely, practical, and strategic legal advice, support and counsel related to a variety of legal issues, including litigation, privacy and human resources matters.
• Expertly assist in overseeing and effectively managing, directly or through external counsel, litigation and other disputes, including representing OLG before courts and tribunals as assigned.
• Apply experience and expertise to identify and recommend practical and effective strategies, controls and measures that mitigate legal and business risk.
• Work closely with senior leaders and functional units to advise on actual or potential areas of litigation or other legal risks and provide advice and recommendations to avoid or minimize risk and to prevent its occurrence.
• Monitor the ongoing effectiveness of the litigation management program, recommend operational opportunities, and provide guidance in implementation as the business and environment evolve and change, identifying exposures, gaps and/or trends and making necessary adjustments.
• Actively liaise with Provincial Government, tribunal bodies, external litigation counsel and other Government stakeholders as required for information exchange.
• Represent OLG in negotiations and meetings with counterparts and stakeholders to strategically advance and promote OLG’s objectives.
• Provide leadership and guidance in the development and implementation of policies, procedures and standards to ensure compliance with applicable laws and regulations to protect OLG’s integrity and periodic review and updating of same.
• Provide mentorship and leadership to Senior Legal Counsel, Legal Counsel, Articling Students, Summer Students and Executive Assistants in order to ensure the success of the legal team.
• Manage and monitor legal expenses to ensure consistent alignment with the department’s fiscal mandate.
• Conduct periodic training sessions on latest developments in these areas for GLC and internal clients.
• Conduct and/or oversee workplace investigations.

Benefits

• Comprehensive, employer-paid group benefits coverage.
• Participation in a performance-based incentive plan that recognizes organizational and individual achievements
• Participation in a highly desirable defined benefit pension plan.
• Competitive paid time-off provisions to support work-life balance and well-being.
• Become your best self with comprehensive support for your professional development.
• Core to OLG’s culture, empowering employees to bring their authentic selves and make a meaningful impact across Ontario.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior