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 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

- 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 explicit direction for technical delivery teams
- Solid 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.

📌 Sr. Product Manager to lead roadmap and delivery for enterprise AI solutions (Toronto)
🏢 S.i. Systems
📍 Toronto