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

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

Solid 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

Career 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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📌 Engineering Manager, ContentIQ Toronto · → (Ontario)
🏢 symplistic.ai
📍 Ontario