Policyme

Principal Product Designer (Remote)

Job Description

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

    • Apply Now
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