Stikeman Elliott is building its own agentic AI platform, with production agents working alongside lawyers on the firm’s matters. This is the senior engineering role responsible for advancing its development. You will design, build and deploy the firm’s AI applications end to end, including production agentic systems, MCP servers that connect to document, email, matter, billing and CRM systems, and reusable plugins and skills that standardize legal and business workflows.

This is a hands-on senior engineering role that spans application architecture, software development and production delivery. You will also provide technical leadership to a small team, with direct access to the firm’s CIO and Enterprise Architect. Own application architecture, including service decomposition, data persistence, state and concurrency models, failure handling, and component interfaces.

Agentic AI Development Extend reusable plugins and skills that standardize the firm’s legal and business workflows. Design human-in-the-loop controls for high-risk agentic actions. Serve as the senior technical escalation point for AI applications.

Build integrations with the firm’s core systems, including document and email management, practice and matter management, time and billing, CRM, enterprise data platforms, and Microsoft Graph. Establish engineering standards across AI repositories, including repository structure, branching, releases, code review, CI gates, environment promotion, and secrets management. Lead code reviews for AI applications and plugin contributions, while mentoring developers on engineering practices.

Build and maintain CI/CD pipelines and strengthen the software supply chain in collaboration with Information Security through automated testing, code quality controls, security scanning, dependency management, and secure application credentials. Minimum of five years of experience designing and delivering production software, including at least one year working directly with LLM-powered or agentic applications in production.



Demonstrated end-to-end ownership of production applications, from architecture and development through deployment and ongoing support.

Proven ability to take solutions from prototype to production and make sound decisions about technical viability.

Experience working as a senior technical contributor in a small, hands-on development workplace. Expert proficiency in Python, including asynchronous development, testing, and modern web frameworks such as FastAPI; working knowledge of TypeScript, Node.js, and front-end development. Production experience with agentic AI, including contemporary agent frameworks, tool calling, orchestration, prompt and context engineering, and MCP servers.

Strong understanding of LLM security and retrieval, including prompt-injection and tool-misuse protections, least-privilege access, data isolation, vector search, embeddings and RAG.

Experience designing production applications and integrations using REST APIs, OAuth 2.0/OpenID Connect, SQL, vector stores, object storage and distributed caching. Strong experience developing cloud applications on Microsoft Azure, including containers, Entra ID, managed identities, Key Vault, managed databases and API Management. Advanced knowledge of GitHub and CI/CD, including code review, Actions, environments, secrets, testing and security controls.

Experience with production observability and AI-assisted development tools such as Claude Code, Cursor, GitHub Copilot or equivalent. Strong technical documentation and communication skills Strong Assets: Microsoft Azure, including containers, Entra ID, managed identities, Key Vault, managed databases and API Management. if your production experience is on AWS or Google Cloud, we expect you to pick it up quickly. Hands-on experience with the Claude Agent SDK, Claude Code plugins and skills, or the Microsoft Graph API.

Experience building software for lawyers, professional services or other regulated, document-heavy environments. Artificial intelligence is used to assist in screening and assessing applications for this position.

Stikeman

Elliott is committed to accommodating people with disabilities as part of our hiring process.

📌 Senior AI Software Engineer (Toronto)
🏢 Stikeman Elliott
📍 Toronto