Senior Manager, AI Engineering in Toronto

KeyCite is a foundational capability within Westlaw. It helps legal professionals understand and navigate legal authority with confidence, including how a case or statute has been treated over time. We are looking for a Senior Manager, AI Engineering to build and lead a team that is evolving KeyCite for the next generation of AI-powered legal research. You will lead engineers across AI, large-scale data processing, backend services, and platform modernization. This is a hands-on technical leadership role. You will lead the team and stay close enough to the technology to make sound architecture and delivery decisions. This role includes both modernizing a critical, long-running platform and building new AI capabilities. The work involves some ambiguity. Priorities are clear, but the approach may change as the team learns and the market evolves.

Key Responsibilities

• Build and lead the team.
• Hire, mentor, and develop a high-performing team of backend, platform, and AI engineers.
• Set technical direction.
• Partner with Product, Editorial, Research, and engineering teams to turn the KeyCite product vision into a scalable technical strategy and roadmap.
• Deliver AI capabilities. Lead the development and productionisation of generative AI and machine learning capabilities that help customers understand legal information and the relationships within it.
• Modernize the platform. Evolve KeyCite's processing, publishing, and services to improve scalability, reliability, and the speed at which new capabilities ship.
• Apply AI to complex domain problems. Work with AI researchers and legal domain experts to decide how generative AI, machine learning, and traditional software can work together in trusted professional workflows.
• Establish engineering excellence. Set standards for architecture, reliability, observability, experimentation, testing, and AI evaluation.
• Take ideas to production. Lead work from prototype through productionisation, measurement, and continuous improvement.
• Lead across boundaries. Remove blockers and build strong working relationships across Engineering, Product, Editorial, and AI teams.

Required Qualifications

• 10+ years experience with at least 7 years of software engineering experience, including work that began before the wide adoption of generative AI and at least 2 years of people-management experience, with teams of 10 or more people, and experience leading multi-team initiatives rather than small groups only.
• Hands-on proficiency in Python and Java, and experience building scalable backend or distributed systems.
• Strong cloud experience, with AWS preferred. Strong experience on Azure or GCP is also considered.
• Experience taking machine learning or generative AI systems from prototype into production.
• Experience leading teams through modernization of existing systems while keeping them reliable.
• Ability to work with ambiguity and drive change in a fast-moving environment.

Preferred Qualifications

• Experience with LLM evaluation, retrieval, grounding, or agent-based architectures.
• Experience in legal technology, legal research, or other regulated or high-accuracy professional-data domains.
• Experience at a company that is actively navigating an AI transformation.
• Experience with data processing at large scale, such as search, knowledge graph, or data platform systems.
• Experience leading or working alongside engineering managers in a matrixed organization.

What’s in it For You?

• Hybrid Work Model: We’ve adopted a flexible hybrid working environment for our office-based roles while delivering a seamless experience that is digitally and physically connected.
• Flexibility & Work-Life Balance: Flex My Way is a set of supportive workplace policies designed to help manage personal and professional responsibilities, whether caring for family, giving back to the community, or finding time to refresh and reset.
• Career Development and Growth: By fostering a culture of continuous learning and skill development, we prepare our talent to tackle tomorrow’s challenges and deliver real-world solutions.
• Industry Competitive Benefits: We offer comprehensive benefit plans to include flexible vacation, two company-wide Mental Health Days off, access to the Headspace app, retirement savings, tuition reimbursement, employee incentive programs, and resources for mental, physical, and financial wellbeing.
• Culture: Globally recognized, award-winning reputation for inclusion and belonging, flexibility, work-life balance, and more.
• Social Impact: Make an impact in your community with our Social Impact Institute. We offer employees two paid volunteer days off annually and opportunities to get involved with pro-bono consulting projects and Environmental, Social, and Governance (ESG) initiatives.
• Making a Real-World Impact: We are one of the few companies globally that helps its customers pursue justice, truth, and transparency.