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Technical Lead
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Engineering Manager – ContentIQ
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…production AI solutions across industries including financial services, retail, hospitality, manufacturing, healthcare, government, and…
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EastSide Centre – Manager on Duty (18 years and older), Part-Time, Year-Round

symplistic.ai

Engineering Manager – ContentIQ

Woodbridge, ON, Canada

Internship

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Job details

Job type: Internship
Apply by: Nov 3, 2026
Experience: 5+ years of professional software engineering experience
Posting language: English
Posted: Oct 4, 2026

Original job description

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 opportunity for career growth as the engineering organization expands
Collaborative, high-energy office environment

Benefits

Sun Life extended health, dental, and wellness benefits.
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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More about this job

Responsibilities

Lead the engineering team and guide ContentIQ’s architecture, roadmap, priorities, and delivery while providing hands-on technical leadership and mentorship. Improve the platform’s RAG, search, document processing, integrations, scalability, reliability, security, and observability, and support enterprise deployments and customer issues.

Requirements

Requires a bachelor’s degree in a relevant technical field, at least five years of software engineering experience, experience leading engineers or technical projects, and strong hands-on skills in Python, React, and machine learning or AI. Candidates should have experience building APIs, microservices, distributed cloud systems, and production-grade software, along with knowledge of databases, modern AI/LLM architecture, and software delivery practices.

Skills

Engineering Leadership
Python
React
Machine Learning
Artificial Intelligence
Large Language Models
Retrieval-Augmented Generation
Enterprise Search
Document Intelligence
API Design
Microservices
Distributed Systems
Cloud Applications
SQL and NoSQL Databases
CI/CD
Customer Support

Benefits

Extended Health Benefits
Dental Benefits
Wellness Benefits
Flexible Vacation
Paid Time Off
Team Off-Sites
Company Events
Professional Development

Visa sponsorship

Not detected in the job text

Keywords

Python
React
Machine Learning
Artificial Intelligence
Large Language Models
Retrieval-Augmented Generation
Enterprise Search
Document Intelligence
Knowledge Management
Embeddings
Reranking
Vector Databases
Milvus
Zilliz
Pinecone
Weaviate
IBM watsonx
watsonx Orchestrate
OpenAI
Groq
Agentic AI
Workflow Orchestration
APIs
Microservices
Distributed Systems
Cloud Applications
SQL
NoSQL
CI/CD
Observability

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