Engineering Manager – Toronto

We are looking for an Engineering Manager to lead the continued development and delivery of ContentIQ, symplistic.ai's enterprise AI knowledge and retrieval platform. ContentIQ connects enterprise information across websites, documents, SharePoint, OneDrive, internal systems, and other data sources to give AI agents secure, governed access to organizational knowledge. It combines enterprise search, RAG, AI-powered document processing, data governance, permissions, integrations, and observability to enable accurate, grounded AI experiences at scale.

This is a technical leadership role for someone who can lead engineers while remaining deeply involved in architecture, product decisions, problem solving, and execution, including assisting in customer deployments and managing issues that may arise. You will work directly with the VP of Engineering and leadership to define technical direction, manage priorities, support enterprise deployments, and scale the platform in performance, reliability, security, and capability.

The work

• Lead the engineering team responsible for the development, delivery, and operation of ContentIQ.
• Work with the VP of Engineering to define technical architecture, engineering priorities, and the ContentIQ product roadmap.
• Translate business and customer requirements into clear technical plans and engineering deliverables.
• Own sprint planning, engineering execution, prioritization, and delivery timelines.
• Provide technical leadership and mentorship to software and AI engineers.
• Review architecture, code, pull requests, and major technical design decisions.
• Help design and improve enterprise RAG, search, document intelligence, ingestion, retrieval, and AI agent capabilities.
• Drive platform improvements across scalability, latency, reliability, security, and observability.
• Support ContentIQ integrations with IBM watsonx and watsonx Orchestrate.
• Establish strong engineering practices around testing, deployment, monitoring, documentation, and production readiness.
• Troubleshoot complex production and customer issues and help the team quickly identify root causes.
• Work directly with enterprise customers when technical discovery, architecture discussions, or implementation support is required.
• Take ownership of features and initiatives from concept through production deployment.

You Required

• Bachelor's degree in Computer Science, Software Engineering, Engineering, or a related technical field.
• 5+ years of professional software engineering experience.
• Previous experience leading engineers, technical projects, or engineering teams.
• Strong hands-on software engineering background.
• Strong experience with Python, React, and ML / AI.
• Experience designing and building APIs, microservices, distributed systems, and cloud-based applications.
• Experience with SQL and/or NoSQL databases.
• Understanding of modern AI/LLM application architecture.
• Strong understanding of software engineering practices including testing, CI/CD, code review, monitoring, and production operations.
• Ability to communicate clearly with engineers, executives, customers, and non-technical stakeholders.
• Strong ownership mentality and ability to operate effectively in a fast-moving startup environment.

Nice to have

• Experience building RAG, enterprise search, knowledge management, or document intelligence and data intelligence platforms.
• Experience working with LLMs, embeddings, reranking, vector databases, and semantic search.
• Experience with vector databases such as Milvus, Zilliz, Pinecone, Weaviate, or similar technologies.
• Experience with distributed caching architectures.
• Experience with agentic AI systems and workflow orchestration.
• Experience with IBM watsonx, watsonx Orchestrate, OpenAI, Groq, or comparable AI platforms.
• Experience working directly with enterprise customers.
• Previous experience in a startup or high-growth technology company.

Candidates must be legally authorized to work in Ontario, Canada.

Life here

• Work from our Canadian headquarters in the Greater Toronto Area.
• Leadership role within a fast-growing enterprise AI company.
• Direct influence over the architecture and roadmap of ContentIQ.
• Work on production AI systems used by major enterprise organizations.
• Exposure to cutting-edge AI, agentic AI, RAG, enterprise search, and orchestration technologies.
• Flat organizational structure with significant autonomy and ownership.
• Direct access to company executives, founders, customers, and technology partners.
• Strong opportunity for career growth as the engineering organization expands.
• Collaborative, high-energy office environment.
• Flexible vacation policy and paid time off.
• Team off-sites and company events.
• Professional development and continued exposure to emerging AI technologies.

We review every application carefully. Only candidates selected for an interview will hear back.