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PolicyMePO

Senior Product Designer

PolicyMe is a Canadian digital insurance provider offering life, critical illness, and health & dental insurance through a streamlined online platform, focused on affordability and accessibility.

PolicyMe

Employee count: 51-200

Salary: 110k-154k CAD

Canada only

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Overview of the role:

Join us at PolicyMe! We’re modernizing insurance and we’d like your help. The Canadian insurance landscape has remained largely unchanged for decades, and we’re leading the charge to make it more accessible, intuitive, and customer-centric. We’re a remote-first, Toronto-based startup with big ambitions.

We’re looking for a Sr.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'll 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
  • Compensation: The total target cash compensation for this role is $110,000–$154,000 CAD, based on experience. We’ll walk through the details together during the interview.

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 www.policyme.com.

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.

About the job

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Posted on

Job type

Full Time

Experience level

Salary

Salary: 110k-154k CAD

Experience

5 years minimum

Location requirements

Hiring timezones

Canada +/- 0 hours

About PolicyMe

Learn more about PolicyMe and their company culture.

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PolicyMe is revolutionizing the Canadian insurance landscape through groundbreaking technology and a steadfast commitment to customer-centric innovation. Founded in 2018 by a team of insurance experts and technology entrepreneurs, PolicyMe is dedicated to making insurance simpler, more accessible, and affordable for all Canadians. The company leverages a sophisticated digital platform to streamline the traditionally complex and often opaque process of obtaining insurance. This technology-first approach allows PolicyMe to offer a seamless, end-to-end online experience, from personalized advice and quote comparison to policy application and issuance, often in a matter of minutes rather than weeks. By significantly reducing inefficiencies and operational costs, PolicyMe consistently provides more affordable coverage options without compromising on quality or protection.

At the core of PolicyMe's innovative model is its proprietary technology that automates many aspects of the life insurance value chain. This includes advanced data analytics and an AI-driven infrastructure to enhance underwriting processes, optimize customer touchpoints, and personalize the insurance journey. PolicyMe offers a comprehensive suite of products, including Term Life Insurance, Critical Illness Insurance, and Health & Dental Insurance, all tailored to meet the evolving needs of Canadian families. The company is not only focused on direct-to-consumer offerings but also provides robust B2B2C solutions, partnering with leading financial institutions and organizations to embed its digital insurance platform, thereby expanding access to millions more Canadians. This dual approach, combined with a commitment to transparency and human support when needed, positions PolicyMe at the forefront of the AI-driven transformation in the insurance industry, striving to close coverage gaps and ensure every Canadian has access to the financial protection they deserve.

Employee benefits

Learn about the employee benefits and perks provided at PolicyMe.

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Stock options

Eligible employees have access to stock options.

Remote-first team

The company operates with a remote-first culture.

Performance reviews twice a year

Performance reviews are conducted twice annually.

Company paid, in-person socials

PolicyMe organizes company-paid in-person social events.

View PolicyMe's employee benefits
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PolicyMe

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