Legal AI Director

Hybrid (Canada)
October 9, 2025
Salary
$
180000
 - 
$
220000
Job Type
Full Time
Years of Experience
8
 - 
15
 years
Industry
Law Practice

Job Description



This company is hiring a Legal AI Director to lead responsible AI implementation across its legal services. Reporting to the CIO, this hybrid role in Canada is pivotal in integrating emerging technologies to enhance legal decision-making, risk management, compliance, and operational efficiency. The successful candidate will champion innovation, drive strategic initiatives, and foster a culture of continuous improvement and ethical AI use.

This is a unique opportunity to work at the forefront of legal technology in a collaborative and inclusive environment that values innovation and impact.
 

Responsibilities



Strategic Leadership
 
  • Define and lead the firm’s AI and innovation strategy aligned with broader organizational goals.
  • Advise leadership on legal, ethical, and regulatory implications of AI technologies.
  • Promote AI literacy and a culture of innovation across teams and departments.
  • Collaborate with internal and external stakeholders, including clients and global innovation leads.

AI Implementation & Oversight
 
  • Oversee selection and deployment of AI tools for legal workflows (e.g., contract review, compliance).
  • Ensure seamless integration of legal tech with IT and legal systems.
  • Partner with vendors and internal teams to enhance legal service delivery through automation and workflows.
  • Monitor emerging technologies and identify opportunities for implementation.

Risk Management & Compliance
 
  • Ensure compliance with legal, ethical, and data governance standards in AI initiatives.
  • Oversee AI governance including transparency, bias mitigation, and auditability.
  • Develop internal policies and training on responsible AI use in legal contexts.
  • Implement secure systems for sensitive legal data.

Process Optimization
 
  • Lead process redesign to improve efficiency across legal and business services.
  • Standardize service delivery models such as matter and contract lifecycle management.
  • Use data to identify inefficiencies and measure performance improvements.
  • Provide regular reporting and manage the AI and innovation budget.

Team & Leadership Engagement
 
  • Serve as a member of the IT leadership team and contribute to firm-wide planning.
  • Collaborate cross-functionally to deliver business-aligned technology solutions.
  • Communicate AI strategies and innovations effectively to technical and non-technical audiences.
 

Requirements

 
  • 10+ years of experience in legal operations, technology, or innovation leadership roles.
  • Located in proximity to one of the company's Canadian offices (Vancouver, Calgary, Toronto, Ottawa, Montreal, Quebec City) and comfortable with a hybrid work environment, 4 days a week in office.
  • Proven success leading AI or digital transformation initiatives in a professional services or regulated environment.
  • Strong knowledge of AI tools, legal tech (e.g., Harvey, Microsoft Copilot), and data governance practices.
  • JD or equivalent legal degree and active membership in a Canadian law society are assets, not requirements.
  • Experience with design thinking, Agile, or process improvement methodologies.
  • Strong communication and stakeholder management skills.
  • Ability to lead change, navigate complex systems, and drive cross-functional collaboration.
  • Proficiency in French is considered an asset.
 

Benefits

 
  • Competitive salary starting from $180,000+ based on experience
  • Flexible hybrid work model with options across Canadian office locations
  • Retirement savings plan with employer contributions
  • Comprehensive benefits with premiums covered by the company
  • Flexible health and wellness allowance (beyond gym memberships)
  • Access to telemedicine services
  • Ongoing learning and development opportunities
  • Inclusive and equitable workplace culture that supports all career paths

Toast's Process

1. Application Review

Submit your application, including your resume and cover letter, through our online portal. Our team will carefully review your qualifications and experiences. We take pride in responding promptly, so if your application aligns with our current opportunities, you’ll hear back from us with next steps. Your journey with Toast begins here, and we’re excited to see what you bring to the table!

2. Vetting Call

If your application is successful, we’ll schedule a vetting call with a member of the Toast team. This 30-45 minute informal conversation is designed for us to get to know you better and assess your skills. Be prepared to discuss your past projects, the challenges you’ve tackled, and the impact you’ve made. This is your chance to shine and show us why you’re a great fit for the roles we offer.

3. Profile Creation

Once you’ve impressed us in the vetting call, we’ll create an unbiased profile that highlights your experience while minimizing common biases. Instead, we focus on your skills, industry experience, and the impact you’ve made. This way, your profile reflects your true potential and accomplishments.

4. Client Submission

After crafting your unbiased profile, we submit it to our trusted clients. We work closely with these clients to ensure they understand the value you bring. Throughout their interview process, we remain by your side, providing support and guidance. Our goal is to help you navigate the hiring process smoothly and confidently, ensuring you have the best chance to secure a role that fits your skills and aspirations.