Join the ranks of Stikeman Elliott, one of the most distinguished and respected corporate law firms in Canada. Our Toronto office is located in the heart of the financial district, with prime access to public transit, which makes it ideal for commuters. The Senior AI Software Developer will design, build, and deliver the firm’s AI applications, including production agentic systems using the Claude Agent SDK, MCP tool servers that connect AI agents to the firm’s systems of record, and reusable plugins and skills for legal and business workflows.

This senior, hands-on role spans application architecture, development and production delivery, with responsibility for technical leadership and mentoring within the team. 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 environment. 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 modern 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. Robust technical documentation and communication skills.

Stikeman

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

📌 Senior Software Developer (Ruby), Remote (Toronto)
🏢 Stikeman Elliott
📍 Toronto