Reports To: CEO

Works Closely With: CTO, Sales & Marketing, Development

Company Description Contextere is a Canadian AI software company headquartered in Ottawa, Ontario, specializing in artificial intelligence software for industrial applications. The company’s flagship solution, the Madison Insight Engine and Blue Collar Co-Pilot, delivers real-time, contextual guidance to frontline workers in complex industrial environments.

Madison is designed to work with small, secure datasets and integrates into existing workflows to transform siloed enterprise information into actionable intelligence for installation, maintenance, and repair. Contextere serves Global 2000 industrial companies, aerospace & defense organizations, and public sector customers, partnering with global leaders such as ABB, Calian, and Lockheed Martin. The organization maintains a lean, innovation-driven structure, with cross-functional teams in R&D;, sales and marketing, and operations supported by experienced directors and advisors.

Position Overview

We are seeking an experienced Product Manager to drive the execution of Contextere's AI-powered solutions. This individual will serve as the bridge between customers, development, operations, and leadership. They will transform customer challenges into scalable commercial features and ensure our product roadmap delivers measurable value to both customers and the business.

The ideal candidate combines expertise in product management with a robust understanding of enterprise software, industrial operations, artificial intelligence, and customer-centric innovation.

Responsibilities

Product Roadmap & Release

- Prioritize features based on customer value, strategic importance, and resource constraints
- Define product requirements, use cases, and user personas
- Product Release plans and execution (including partner releases)
- Value proposition and ROI
- Identify common requirements across customers and convert them into repeatable product capabilities





Customer Discovery & Market Validation

- Conduct regular customer interviews and discovery sessions
- Validate product-market fit and prioritize opportunities based on commercial impact
- Market research and analyst engagement
- Competitor analysis and tracking
- LinkedIn tracking and engagement

Cross-Functional Engagement

- Partner with Development to guide feature development
- Work closely with Customer Success and Deployment teams to capture user feedback
- Collaborate with Sales and Marketing on product positioning, messaging, PR and demonstrations
- Support proposal development and strategic customer engagements
- Support security and compliance requirements (SOC, ISO)

Onboarding & Growth

- Define and manage the customer onboarding process
- Contribute to pricing and packaging strategies
- Support enterprise sales efforts and customer workshops
- Help identify expansion opportunities within existing accounts
- Track product adoption, utilization, and business outcomes

Qualifications

Required

- 5+ years of Product Management experience
- Experience with SaaS, enterprise software, AI, analytics, or digital platforms
- Proven ability to manage customer requirements and product roadmaps
- Strong communication and stakeholder management skills
- Experience working with software development teams

Preferred

Experience in

- Artificial Intelligence
- Machine Learning
- Aerospace & Defence
- Industrial Operations
- Asset Management
- Workforce Management
- Digital Transformation

Ideal Candidate Profile You are someone who can walk into a Lockheed Martin meeting in the morning, discuss competency management and workforce readiness, spend the afternoon prioritising AI features with engineering, and finish the day helping Sales position Madison against competing solutions.

You are equally comfortable discussing customer workflows, product strategy, commercialization, and technical architecture. You thrive in fast-growing companies where ambiguity exists, decisions matter, and product leadership directly influences company success.

📌 Product Manager (Ottawa)
🏢 Contextere
📍 Ottawa