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 PolicyMe 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.

What you will be doing:

• 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.

What we are looking for:

• 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.

The ideal candidate will have:

• 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, wireframing, 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 when to assert, when to ask, and when to adapt.

Why join us:

• Generous PTO - 20 vacation days
• A comprehensive benefits plan with premiums paid in full by PolicyMe
• Investment in your professional development, including an L&D budget, AI tooling budget, performance reviews twice a year and ongoing feedback to ensure you reach your highest potential
• An extremely high performing, low-ego, remote-first team that is truly disrupting an old industry
• Option to work from home or our Toronto-based office (bonus: we cover the costs to bring all our employees in-person twice a year for experiential socials!)
• Access to stock options based on performance

About PolicyMe:

At PolicyMe, we are Canada’s leading digital insurance solution, offering straightforward and affordable financial protection for families from coast to coast. Our product suite includes Life Insurance, Critical Illness Insurance, and Health & Dental Insurance, all tailored to Canadians' evolving needs. We also offer B2B2C solutions, partnering with organizations to provide seamless digital insurance options. Founded by a team of insurance experts and technology entrepreneurs, PolicyMe is committed to making insurance simpler and more accessible. Since our launch in 2018, we have grown exponentially, selling over $10 billion in insurance coverage to Canadians.

We are proud of the team we’ve built and are excited for those that are yet to join us. We operate with a remote-first culture, attracting top talent from across Canada. If you’re looking for a fast-paced, collaborative environment, working alongside incredibly ambitious yet humble humans, we may be the right place for you! To learn more, visit  .

Additional Notes

- Job Vacancy: This role reflects growth in our team and expanded operational scope. We’re hiring to support increasing demand and continue delivering an exceptional customer experience.

- Commitment to Equal Opportunity: PolicyMe is an equal opportunity employer. We welcome applicants of all backgrounds and provide fair consideration regardless of race, colour, religion, sex, sexual orientation, gender identity, national origin, or disability.

- Accessibility Statement: We are committed to providing an accessible hiring experience. If you require accommodations during the application process, please indicate this in the “Additional Information” section of your application.

We thank all applicants for their interest, however, only those selected for an interview will be contacted.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.