Title:  Senior Director Product Design

About The Role

As Senior Director of Product Design, you will lead and grow a multi-layer product design organization responsible for elevating interactions, systems, and end-to-end experiences across a highly complex suite of enterprise software and consumer-facing digital products in food retail, food service, and hospitality space.

This role is pivotal to maturing Product Design into a core strategic driver of business outcomes. You will define the quality bar, shape design operations and systems, and influence product direction through clarity of thinking, strong judgment, and disciplined execution.

You will operate in an environment with high ambition, competing priorities, and strong cross-functional perspectives—particularly across Product Management and Engineering. Success requires maturity, negotiation strength, and comfort operating without perfect clarity.

You’ll work alongside a high-calibre group of leaders and practitioners with backgrounds spanning IDEO, frog, Fjord, McKinsey Design, and high-growth startups. This is a team that values rigor over theater, healthy debate over harmony, product over process, and outcomes over output.

This role is for a design leader who thrives in ambiguity, remains steady under pressure, and sees complexity as an opportunity to create clarity, leverage, and durable impact.

You will report directly to the VP of Design and serve as a key partner in advancing Design as a respected, enterprise-level capability.

Department: Design

Location: 72 Fraser Avenue, Toronto, Canada

Work Model: Hybrid (4 days in-office)

Job Summary

Now, if you were to come on board as our Senior Director, Product Design-, we’d ask you to do the following:

Lead the Product Design Practice at a Leadership Level

• Set and evolve a portfolio-level product design vision across enterprise platforms and customer-facing channels.
• Lead, coach, and scale a multi-layer design organization (Directors, Managers, Principals, and Senior ICs).
• Represent Design with confidence in senior and executive forums, advocating for experience quality, scope discipline, and long-term product health.
• Model calm, decisive leadership in fast-moving, high-pressure environments.

Navigate Complexity & Influence Outcomes

• Diplomatically navigate organizational friction without escalation—earning trust while holding firm on design standards.
• Partner closely with Product and Engineering leaders, developing deep empathy for their constraints while challenging assumptions and unrealistic scope.
• Negotiate trade-offs with clarity and conviction—knowing when to push, when to reframe, and when to say no.

Elevate Craft, Systems & Thinking

• Move the organization beyond “screens” toward systems thinking, service design, and operationally-aware experiences.
• Push the boundaries of UX/UI by exploring AI as an interface, not just a feature—rethinking workflows, decision support, and human–machine collaboration.
• Grow and evolve design systems, content, and accessibility practices to scale quality and consistency across products.

Outcomes over Output

• Champion a problem-first mindset, designing for outcomes rather than output.
• Ensure design work holds up in real physical operational environments, not just ideal scenarios.
• Establish clarity around 

Think you have what it takes to be our Senior Director of Product Design? We’re committed to hiring the best talent for the role. Here’s how we’ll know you’ll be successful in the role.

• 12–15+ years in Product Design, with 5+ years in senior leadership roles.
• Proven experience designing for complex enterprise and operational software.
• Demonstrated ability to lead 10–20+ designers across multiple teams or product lines.
• xperience partnering with executive leadership and translating design value into business terms.
• A track record of delivering measurable business impact through design-led initiatives or transformations.
• Strong expertise in interaction and visual design, grounded in systems-level thinking.
• Demonstrated experience with organizational planning, resource negotiation, and budget ownership.
• Fluency in DesignOps, design systems, and cross-functional collaboration at scale.
• Familiarity with AI