Director, Product Management

Title: Director, Product Management Location: Mississauga, Ontario, Canada

Director of Product Management

About Upshop: 

Upshop is the foremost provider of a SaaS platform designed to streamline forecasting, ordering, production, and inventory optimization for food retailers and foodservice operators. Our unified platform simplifies and enhances daily workflows, enabling smarter, more connected operations across fresh production, inventory management, food safety, and ordering.

Trusted by over 450+ retailers and operators across 50,000+ locations globally, Upshop helps customers improve sales, reduce waste, increase operational efficiency, and advance food safety and sustainability—especially in complex, production-driven environments.

Role Overview

Upshop is seeking a Director of Product Management to oversee the strategy, development, and delivery of product capabilities across two distinct core products within Upshop’s retail operations platform. In this leadership role, you will be responsible for defining the overarching product vision and leading a small, high-performing team of 2 Product Managers/Owners to drive operational efficiency, reduce waste, and maximize profitability for grocery retailers.

You will act as a strategic bridge between executive leadership, engineering, design, data science, and revenue teams. The ideal candidate has deep expertise in enterprise SaaS environments, a proven track record of scaling product teams, managing multiple-products, and demonstrated experience of building AI driven intelligent capabilities in the product. 

Key Responsibilities

Portfolio Strategy & Leadership:

• Define and execute the long-term vision, product strategy, and unified roadmap across two distinct core product lines.

• Lead, mentor, and scale a small team of 1-2 PMs/POs fostering a culture of continuous discovery, operational empathy, and high accountability.

• Establish product management best practices, frameworks, and success metrics (KPIs/OKRs) to measure portfolio health and delivery velocity.

• Align product priorities directly with company-wide strategic objectives and growth targets.

Product Development & Delivery Oversight:

• Partner with Engineering and UX leadership to establish robust processes for cross-functional collaboration and scalable delivery.

• Oversee agile processes across teams, ensuring high-quality roadmap execution, proactive backlog management, and predictable release planning.

• Drive platform scalability, ensuring features meet strict compliance, usability, data integrity, and performance standards.

Market, Customer, & Stakeholder Engagement:

• Engage directly with executive-level customer champions and retail operators to understand complex industry workflows and market shifts.

• Synthesize insights from Sales, Revenue, and Customer Success teams to validate high-value portfolio opportunities.

• Act as the primary internal and external evangelist for your product portfolio, communicating strategy and product updates across the company.

Innovation & Technical Architecture Alignment:

• Steer the integration strategy for the portfolio, ensuring seamless communication with complex retailer tech stacks, APIs, and enterprise systems.

• Champion AI-driven innovation, identifying opportunities to embed machine learning, predictive analytics, and automated workflows into the SaaS products.

Qualifications

Required Experience:

• Product Experience: 5-7+ years of total software product management experience in a SaaS or enterprise software environment.

• Leadership Experience: Proven experience directly managing and developing full-time Product Managers for 2+ years

• Portfolio Management: Prior ownership of multiple products or highly complex, multi-module enterprise software platforms.

• Execution: Strong mastery of agile methodologies, product discovery frameworks, and cross-functional leadership.

• Education: Bachelor’s degree in Business, Computer Science, Engineering, or a related field (or equivalent practical experience).

Technical & Innovation Competencies:

• Architecture: Strong working knowledge of enterprise SaaS architecture, modern API frameworks, and third-party integrations.

AI & Analytics: Hands-on fluency with AI-enabled tools, and the judgment to guide teams in designing AI-driven features that solve real customer problems. You define the analytics and success metrics that prove the value and ROI our products deliver.

• Communication: Exceptional storytelling and stakeholder management capabilities, with the ability to confidently present technical roadmaps to non-technical executive audiences.

Preferred Experience:

• Industry Vertical Domain knowledge in grocery retail tech, supply chain automation, inventory management, or food retail operations.

• Data Scale: Experience leading data-dense products that rely heavily on data science, machine learning models, or automated forecasting.

Working Relationships:

This role collaborates closely with:

• Engineering Leadership (VP/Directors of Engineering)

• Data Science & Analytics Teams

• Product Marketing Teams

• Revenue & Sales Executives

• Customer Success Teams

• Professional Services Teams

The estimated pay ranges for this role are as follows:

• 200,0000 - 250,000 CAD

The successful candidate’s starting salary will be determined based on permissible, non-discriminatory factors such as skills, experience, and geographic location.