AI Manager Remote (Toronto, ON) Long term contract
We are seeking an accomplished AI Architect / AI Engineering Manager to lead the modernization and transformation of a mission-critical legacy enterprise benefits administration platform using modern AI engineering practices, cloud-native architecture, and agent-based development workflows. This is a hands-on technical leadership role for an architect and engineering leader who can define the target-state architecture, establish AI-assisted engineering practices, guide a high-performing engineering team, and drive the delivery of scalable, secure, and exceptional enterprise applications. The successful candidate will combine deep expertise in software architecture, full-stack engineering, AI/GenAI technologies, cloud platforms, and engineering leadership with the ability to translate complex business requirements into pragmatic technical strategies. The role will leverage emerging AI-assisted development technologies and coding agents including Claude, Codex, and similar AI engineering platforms to accelerate modernization, improve developer productivity, automate engineering workflows, and enable new approaches to software delivery.
Required Qualifications & Experience
Bachelor's degree in Computer Science, Engineering, Information Technology, or a related discipline.
10+ years of software engineering experience, with significant experience in architecture and technical leadership.
Demonstrated experience as a Software Architect, AI Architect, Principal Engineer, Engineering Manager, or equivalent senior technical leadership role.
Strong full-stack engineering background across modern frontend and backend technologies.
Proven experience architecting and modernizing large-scale legacy enterprise applications.
Hands-on experience with AI-assisted software development tools, coding agents, LLMs, or agentic engineering workflows.
Experience with Claude, Codex, GitHub Copilot, or comparable AI coding and engineering platforms.
Experience with React, TypeScript, Node.js, Python, Java, or comparable modern technology stacks.
Strong understanding of enterprise application architecture, distributed systems, APIs, microservices, event-driven architectures, and integration patterns.
Strong frontend architecture and engineering experience with a focus on modern enterprise UX/UI.
Strong backend engineering experience with scalable, resilient APIs and services.
Deep understanding of cloud-native architecture and modern DevOps/DevSecOps practices.
Experience leading architecture decisions and influencing engineering teams without relying solely on organizational authority.
Excellent problem-solving, communication, stakeholder-management, and technical leadership skills.
Preferred Qualifications:
Experience with Generative AI, LLM applications, RAG, AI agents, agentic workflows, prompt engineering, or AI orchestration frameworks.
Experience establishing enterprise AI engineering standards, governance, and responsible-use practices.
Experience designing multi-tenant, highly configurable enterprise SaaS platforms.
Experience with AWS, Azure, Google Cloud Platform, or other major cloud platforms.
Experience with Kubernetes, containers, serverless architectures, infrastructure-as-code, CI/CD, and observability platforms.
Experience in benefits administration, HRTech, FinTech, insurance, healthcare technology, or enterprise SaaS.
Experience modernizing applications while maintaining critical legacy integrations and business rules.
Experience working in Agile product-development organizations.
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