Sr. Product Manager to lead roadmap and delivery for enterprise AI solutions

Location: 3-4 days on-site per week, primarily downtown Toronto near Bathurst & Lakeshore; North Mississauga may also be considered

Contract Duration: Until the end of 2027

Overview
Our enterprise retail client is looking for a Sr. Product Manager to support a newly forming AI Development pod focused on delivering Agentic AI solutions across the organization.

The team will be working with business and product groups across areas such as Loyalty, Pricing, Marketing and Fraud to identify and deliver AI use cases. This person will work closely with the AI Development Lead and technical team to organize incoming demand, define priorities, build the product roadmap and help move solutions from business need through delivery.

The majority of the role will support the AI portfolio , with additional involvement across digital products and services including mobile, e-commerce and gift cards.

This is a hands‑on Product Management role requiring someone who can understand business needs, work effectively with technical teams and bring structure and prioritization to a rapid‑moving portfolio.

Must-Haves

7+ years of hands‑on Product Management experience within complex enterprise environments

Experience managing AI, Generative AI or data/AI-driven products and initiatives

Strong experience developing and managing product roadmaps, backlogs and priorities

Experience translating business use cases and requirements into clear direction for technical delivery teams

Strong technical understanding with experience working closely with software engineering, data and/or AI teams

Experience managing multiple use cases, stakeholders and competing priorities across a portfolio

Strong strategic thinking with the ability to connect business needs to product priorities and delivery

Excellent communication and presentation skills , with the ability to communicate clearly and concisely with technical teams, business stakeholders and senior leadership





Nice-to-Haves

Experience with Agentic AI, LLM or Generative AI products

Product experience within retail, grocery, banking or telecommunications

Experience supporting customer‑facing digital products such as mobile or e‑commerce

Experience working within Agile product and engineering team

Experience working with Jira and Confluence

Interview Process

Round 1: 30‑minute introductory interview with the hiring team

Case Study: Candidates will receive a Product Management case study with approximately 72 hours to prepare and submit their response in advance, followed by a 30‑minute discussion focused on their approach, priorities and recommendations

Round 2: Interview with additional Product Management stakeholders

Location: 3-4 days on‑site per week, primarily downtown Toronto near Bathurst & Lakeshore; North Mississauga may also be considered

Contract Duration: Until the end of 2027

Overview
Our enterprise retail client is looking for a Sr. Product Manager to support a newly forming AI Development pod focused on delivering Agentic AI solutions across the organization.

The team will be working with business and product groups across areas such as Loyalty, Pricing, Marketing and Fraud to identify and deliver AI use cases. This person will work closely with the AI Development Lead and technical team to organize incoming demand, define priorities, build the product roadmap and help move solutions from business need through delivery.

The majority of the role will support the AI portfolio , with additional involvement across digital products and services including mobile, e‑commerce and gift cards.





This is a hands‑on Product Management role requiring someone who can understand business needs, work effectively with technical teams and bring structure and prioritization to a fast‑moving portfolio.

Must-Haves

7+ years of hands‑on Product Management experience within complex enterprise environments

Experience managing AI, Generative AI or data/AI-driven products and initiatives

Strong experience developing and managing product roadmaps, backlogs and priorities

Experience translating business use cases and requirements into clear direction for technical delivery teams

Strong technical understanding with experience working closely with software engineering, data and/or AI teams

Experience managing multiple use cases, stakeholders and competing priorities across a portfolio

Strong strategic thinking with the ability to connect business needs to product priorities and delivery

Excellent communication and presentation skills , with the ability to communicate clearly and concisely with technical teams, business stakeholders and senior leadership

Nice-to-Haves

Experience with Agentic AI, LLM or Generative AI products

Product experience within retail, grocery, banking or telecommunications

Experience supporting customer‑facing digital products such as mobile or e‑commerce

Experience working within Agile product and engineering team

Experience working with Jira and Confluence

Interview Process

Round 1: 30‑minute introductory interview with the hiring team

Case Study: Candidates will receive a Product Management case study with approximately 72 hours to prepare and submit their response in advance, followed by a 30‑minute discussion focused on their approach, priorities and recommendations

Round 2: Interview with additional Product Management stakeholders

Disclaimer:
AI may be used in evaluating candidates.
This posting is for an existing vacancy.
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📌 Sr. Product Manager to lead roadmap and delivery for enterprise AI solutions (Ontario)
🏢 S.i. Systems
📍 Ontario