Osler, Hoskin & Harcourt LLP is one of Canada’s leading business law firms. Advising many of Canada’s corporate leaders, as well as U.S. and international parties with extensive interest in Canada, our more than 1,000 firm members are based in offices in Toronto, Montréal, Ottawa, Vancouver, Calgary and New York.

Osler prides itself on attracting and maintaining some of the brightest talent in the legal arena. Our lawyers, students, management and staff have created a unique firm culture which nurtures mentoring and the exchange of ideas. Osler is a dynamic and exciting place to begin a career or carve out a new path.

We are seeking a hands‑on and technically savvy AI Workflow Lead with legal practice experience to help our lawyers turn ideas into working AI solutions. Reporting to the Director, AI & Technology, this role sits at the intersection of legal practice, applied AI, and knowledge engineering, and is responsible for managing the intake and delivery of AI agent and workflow initiatives across the firm’s practice groups. The successful candidate will work directly with lawyers to scope, build, and track solutions using firm‑approved platforms.

This job posting is for an existing vacancy.

Major Responsibilities

Manage the intake pipeline for AI workflows and agents, including triaging, prioritizing, and tracking incoming initiatives from practice groups

Conduct scoping sessions with lawyers to assess workflow challenges, define requirements, and identify the appropriate path forward using firm‑approved AI tools and platforms

Advise lawyers and practice group members on the selection and application of firm‑approved AI platforms, providing clear recommendations tailored to each use case

Design and build AI agents and workflows using approved platforms, independently or in collaboration with stakeholders





Maintain a centralized project tracker and provide regular status updates to stakeholders

Collaborate with the firm’s training and curriculum function to ensure that capability‑building programs connect to the practical application of AI tools

Stay current with developments in AI agent platforms, tools, and techniques relevant to legal workflows, and contribute to the evaluation of recent tools and capabilities as directed

Assist with other matters within the AI and Legal Operations team as and when required

Position Requirements Education and Experience This position requires a J.D., bachelor or graduate degree in a related field (e.g., business administration, computer science, data science, knowledge management), with ideally 1-3 years of experience working in or closely with a legal practice environment (e.g., legal practice, legal operations, legal technology, or in‑house innovation). Experience in a professional services environment is an asset. An equivalent combination of education, training and experience may be acceptable.

Knowledge and Skills

Strong understanding of the structure and operations of full‑service firms, including practice groups and typical workflows

Demonstrated AI‑first mindset, with a proactive approach to leveraging AI tools to solve business and legal challenges

Strong familiarity with legal practice, with credibility and judgement to engage effectively with partners and senior lawyers on the application of AI in legal work

Technical fluency in AI systems (prompt engineering, RAG, context optimization)



and knowledge engineering

Hands‑on, solution‑oriented approach with experience developing and deploying practical tools and iterating quickly in a dynamic, fast‑paced environment

Excellent consultative communication skills, with the ability to lead scoping conversations with lawyers and translate ideas into clear, actionable deliverables

Organized and proactive, with project management skills to run a pipeline of concurrent work across practice groups and platforms

Compensation Compensation will be determined based on a variety of factors including year of call, job‑related knowledge, education, skills and experience.

We are currently working in a hybrid work arrangement, which includes a requirement to work primarily in the office and flexibility to work remotely up to 2 days per week.

Accessibility and Accommodation We thank all applicants for their interest in Osler; however, only chosen applicants will be contacted. Osler is committed to fostering a diverse and inclusive work environment, and we welcome and encourage applications from people with disabilities and people with diverse backgrounds, identities, and cultures. Accommodations are available upon request for candidates in all phases of the selection process.

Background and Reference Checks Please note that any offer of employment will be conditional upon background and reference checks, including a criminal record check, credit check, and employment and educational verifications.

If you have the required background with the ability to provide exceptional customer service and wish to work in one of Canada’s leading law firms, please reply in confidence with a cover letter and résumé by the closing date.

Please note that we use artificial intelligence to screen, assess or select applicants for the position.

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📌 AI Workflow Lawyer (Toronto)
🏢 Osler, Hoskin & Harcourt
📍 Toronto