Senior Director of Design, Enterprise

Remote · Toronto · 7+ years experience · Posted Oct 14, 2026

At a glance

Toast is seeking a Senior Director of Product Design to shape the Enterprise Core organization and lead design, strategy, and vision across a critical portfolio.
This role involves working across foundational point-of-sale systems, integrated platform ecosystems, and pioneering AI and agentic experiences.
You will collaborate closely with cross-functional teams to deliver highly configurable, performant, and accessible solutions for multi-unit restaurant brands, hotel groups, stadiums, and arenas.

Develop and drive the overall product design vision for the growth organization, aligning it with business goals and user needs.
Build, mentor, and inspire a high-performing design team, fostering a culture of creativity, design excellence, and impact.
Coach team members to continually improve their craft and deliver an exceptional experience.
Leverage qualitative and quantitative research to inform design decisions and continuously improve product experiences.
Use design to drive critical business metrics and KPIs.

7+ years of experience partnering closely with Product, Engineering, and commercial/operational teams to understand enterprise user ecosystems and translate insights into a unified design strategy.
Experience leading design teams in creating intuitive experiences across responsive web, native mobile apps, and dedicated hardware.
Ability to see around corners, anticipating the future and integrating emerging technologies and AI-driven automation into high-volume, live operational environments.
Possess an enduring sense of curiosity with a desire to continuously learn and evolve.
Regularly conduct design reviews to promote a culture of feedback, growth, and iteration.
Demonstrate a growth mindset with the ability to view challenges as opportunities and speak confidently to the why behind designs.

Embraces a hybrid work model that fosters in-person collaboration while valuing individual needs.