Principal Product Designer; Remote

Overview of the role

We’re on a mission to modernize insurance, making it simpler, more accessible, and customer-first. The insurance industry is a $1T market that has remained largely untouched by the digital revolution, and Policy Me is here to change that. As a remote-first, Toronto-based startup with big ambitions, we’re looking for a Principal Product Designer to help us build the future of insurance in Canada and beyond.

We’re looking for a Principal Product Designer to join our product team, where design plays a critical role in shaping customer journeys and driving core business outcomes. This isn’t just a UI design role; you’ll take a proactive role in uncovering opportunities, framing problems, and validating direction with research and data—then lead the design of simple, elegant and conversion-friendly solutions that balance user empathy with business needs.

You’ll set a high bar for craft and polish—from systems thinking and content to interaction details—and you sweat the moments that make complex decisions feel intuitive and effortless. You’ll have ownership, autonomy, and a direct line to shaping how Canadians purchase insurance in Canada.

• Owning the end-to-end design process: from exploratory research to wireframes, prototypes, usability testing, and polished high-fidelity designs.
• Driving deep customer and product understanding through short-form research (customer interviews/surveys, edge case mapping, journey reviews, competitor benchmarking).
• Collaborating closely with product managers, engineers, and stakeholders to define problems, align on outcomes, and craft thoughtful and intuitive solutions.
• Supporting large product initiatives such as major product launches and optimizations of existing customer journey flows (whether complete revamps or smaller-scale A/B tests).
• Using our existing design system to ship consistent, scalable UI while contributing to its ongoing evolution.
• Participating in team rituals such as weekly design reviews, retros, product unite meetings, and daily cross-functional standups.
• Communicating design decisions clearly, telling the story behind your work, and bringing others along with you—including exec-level stakeholders.
• Balancing speed and quality by iterating quickly, working with ambiguity, and refining based on input.
• Bringing a perspective of continuous improvement—whether in our processes, tooling, or how we collaborate as a team.

• We’re looking for a self-driven, collaborative, and highly capable Sr. Product Designer who can work across the full design stack - from discovery to delivery. You’ll thrive in this role if you’re energized by shaping digital products end-to-end, love understanding the “why” behind user behaviour, and bring a sharp eye for detail to every interaction.

• 5+ years of experience designing intuitive, user-centric digital products, ideally in a fast-paced, consumer-focused environment.
• A strong foundation in visual design, interaction design, and information architecture, with a portfolio that demonstrates elegant solutions to complex problems.
• Experience working through the full product design lifecycle - from research and ideation to execution, validation, and iteration.
• Proven ability to conduct or collaborate on user research, synthesize insights, and translate findings into actionable design decisions.
• Comfortable navigating ambiguity and complexity, especially in domains that require simplification of dense or regulated information.
• Demonstrated ability to work collaboratively with cross-functional teams, including product managers, engineers, content strategists, and marketers.
• An iterative mindset with strong prototyping skills - you’re comfortable sketching, wire framing, and building interactive flows to explore ideas and communicate intent.
• Familiarity with design systems and experience contributing to scalable components and patterns.
• Excellent verbal and written communication skills, with the ability to articulate your thinking, frame trade-offs, and align stakeholders on direction.
• A healthy balance of humility, curiosity, and confidence - you know…