About symplistic.ai symplistic.ai is a fast-growing AI company with offices in Florida and Toronto. We specialize in Agentic AI solutions, enterprise consulting, and AI innovation, helping organizations design, build, and deploy intelligent systems that solve real-world business challenges.

Our team works with major enterprise organizations to deliver production AI solutions across industries including financial services, retail, hospitality, manufacturing, healthcare, government, and more.

We operate as a high-velocity startup where ownership, execution, and accountability matter. Our team works closely together, moves quickly, and takes ideas from concept through production.

About Symplistic.ContentIQ Symplistic.ContentIQ is 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 provide AI agents with secure, governed access to organizational knowledge.

The platform combines enterprise search, Retrieval-Augmented Generation (RAG), AI-powered document processing, data governance, permissions, integrations, and observability to enable accurate, grounded AI experiences at scale.

ContentIQ is designed to serve as the enterprise knowledge layer behind AI agents and platforms such as IBM watsonx Orchestrate, enabling organizations to securely connect their existing information to intelligent workflows and conversational experiences.

Role Overview We are looking for an Engineering Manager to lead the continued development and delivery of ContentIQ. This is a technical leadership role for someone who can lead engineers while remaining deeply involved in architecture, product decisions, problem solving, and execution. You will also be responsible for assisting in customer deployments and managing issues that may arise with customers.

You will work directly with symplistic.ai's VP of Engineering and leadership team to help define the technical direction of ContentIQ, manage engineering priorities, support enterprise deployments, and ensure the platform continues to scale in performance, reliability, security, and capability.

This is not a traditional management-only position. We are looking for someone who understands the technology, can challenge technical decisions, jump into difficult engineering problems when necessary, and help a small, high-performing team move quickly.

Key Responsibilities

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

Qualifications 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

Solid hands-on software engineering background

Strong experience with Python, React, 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

Preferred

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

Who We're Looking For We're looking for someone who is comfortable operating between engineering leadership and hands-on technical execution.

You should be someone who:

Takes ownership rather than waiting for direction

Holds engineers to a high standard while helping them grow

Understands the difference between building a prototype and operating enterprise software in production

Is comfortable working directly with customers and executives

Can balance performance, reliability, security, speed, and business priorities

Wants to have a significant influence over the direction of a growing AI platform

ContentIQ is evolving quickly, and this role will have substantial influence over both the product and engineering organization as we scale.

Candidates must be legally authorized to work in Ontario, Canada

Work from our Canadian headquarters in the Greater Toronto Area

Leadership role within a rapid-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 chance 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

Direct collaboration with senior engineers, founders, executives, and enterprise technology leaders

Professional development and continued exposure to emerging AI technologies

Compensation Base Salary: $120,000 CAD per year (Plus performance-based bonus)

Compensation includes opportunities for additional growth as the company and ContentIQ organization scale.

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📌 Engineering Manager, ContentIQ (Winnipeg)
🏢 symplistic.ai
📍 Winnipeg