The posting
This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Head of Product Design based in Canada.
This is a senior player-coach opportunity leading a 15-person product design organization through a period of rapid growth and AI-driven product evolution. You’ll shape design strategy across a sophisticated product portfolio while remaining deeply involved in the craft and execution of the work. The role combines people leadership, product strategy, hands-on design critique, and close partnership with product and engineering teams. You’ll establish a high bar for quality and coherence while empowering autonomous teams to move quickly without unnecessary process. A major focus will be shaping intuitive experiences where AI agents and people work together naturally within product workflows. You’ll represent customer needs at the leadership level while solving complex UX challenges and improving the overall quality of shipped experiences. This role is ideal for a design leader who thrives in ambiguity, values exceptional craft, and enjoys building scalable systems without losing the human side of design.
Accountabilities
- Lead, hire, develop, and retain a high-performing team of approximately 15 product designers, providing direct feedback, coaching, mentorship, and career development.
- Set and execute the design strategy across a broad product portfolio, ensuring consistency, coherence, and a strong overall customer experience.
- Partner with product, engineering, and senior leadership to solve complex UX challenges, establish priorities, and translate customer needs into effective product experiences.
- Remain deeply involved in design execution by pairing with designers, reviewing work, challenging assumptions, and helping teams navigate difficult product and UX problems.
- Champion exceptional visual and interaction design, setting clear standards for quality while avoiding unnecessary approval processes or bottlenecks.
- Advocate for the customer in leadership discussions, pushing for intuitive, simple, and genuinely useful product experiences.
- Help define how AI agents and human users collaborate within product workflows, contributing to the development of AI-native experiences.
- Identify opportunities to improve design systems, team effectiveness, product coherence, and design quality across autonomous product teams.
- Push for thoughtful attention to product details, edge cases, usability issues, and other sources of customer friction.
- Build structure and clarity within a fast-moving organization while preserving team autonomy and execution speed.
- 7+ years of experience in product or UX design, including significant experience in senior individual contributor and/or design leadership positions.
- At least 2 years of experience managing senior or independent designers and developing high-performing design teams.
- Proven experience shipping products that delivered measurable customer and business outcomes.
- Strong product and craft judgment, with the ability to provide clear, specific, and actionable design feedback.
- Demonstrated experience creating structure and scalable ways of working within complex, ambiguous, or high-growth environments.
- Hands-on experience designing AI-native experiences and using AI-powered tools within your own design practice.
- A portfolio demonstrating both systems-level product thinking and strong pixel-level craft.
- Ability to balance speed, autonomy, consistency, and quality across multiple product teams or pods.
- Strong customer empathy and the ability to represent user needs in senior-level product discussions.
- Excellent communication, storytelling, stakeholder management, and executive presence.
- A builder mindset, strong ownership, intellectual curiosity, and comfort navigating ambiguity.
- Experience designing for both technical and non-technical audiences is a plus.
- Experience with analytics, experimentation, developer tools, or similarly complex products is a plus.
- Competitive compensation with location-specific total target cash ranges for eligible Canadian and North American locations.
- Equity eligibility and an Employee Stock Purchase Program (ESPP).
- Medical, dental, and vision insurance, including employer-paid premiums on select plans.
- 401(k) retirement plan with employer matching for eligible employees.
- Flexible time off and paid holidays.
- Monthly wellness stipends and additional support for commuter expenses where applicable.
- Quarterly learning and development stipends.
- New-hire home office equipment support.
- 12 weeks of paid parental leave.
- Fertility, adoption, and surrogacy support through dedicated family benefits.
- Backup childcare support.
- Mental health and wellness benefits, including access to coaching and therapy.
- Mentorship programs, management training, and professional development initiatives.
- Charitable giving grants and paid volunteer time off.
- Remote work environment within the eligible NAMER region.
How Jobgether works:
We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.
We appreciate your interest and wish you the best!
Why Apply Through Jobgether?
Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.
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