Location symplistic.ai Canada Headquarters

Hybrid work schedule: 3–4 days per week in-office

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
- Strong 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
- Experience designing scalable, production-grade software systems
- 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
- Can make pragmatic technical decisions quickly
- Holds engineers to a high standard while helping them grow
- Enjoys solving difficult technical problems
- 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.

Eligibility

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

Perks

- Work from our Canadian headquarters in the Greater Toronto Area
- Hybrid work schedule: 3–4 days per week in-office
- 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 prospect for career growth as the engineering organization expands
- Collaborative, high-energy office environment

Perks

- Flexible vacation policy and paid time off
- Team off-sites and company events
- On-site lunches
- 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.

How to Apply

Please send your resume, cover letter, and any relevant links, projects, GitHub profiles, or examples of previous work to symplistic.ai.

- In your application, we'd especially like to hear about systems or engineering teams you have previously led, and any experience you have building production AI, search, data, or enterprise software platforms.

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