Engineering Manager, Contentiq 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, including as the knowledge layer behind platforms such as IBM watsonx Orchestrate. 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. This is not a traditional management-only position.
Based in symplistic.Ai Canada Headquarters, Woodbridge, Ontario.
symplistic.Ai is a forward-thinking AI company with offices in Florida and Toronto. We specialize in Agentic AI solutions, enterprise consulting, and innovation delivery. Our team builds autonomous AI agents to solve real-world business challenges, delivering scalable, intelligent systems that integrate seamlessly into enterprise environments.
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
YouRequired
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.
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