Job description
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 Life & Critical Illness Insurance 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 be a strategic partner in identifying problems, conducting research, and designing elegant, conversion-friendly solutions that balance user empathy with business needs. 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, edge case mapping, journey reviews, competitor benchmarking).
- Collaborating closely with product managers, engineers, and stakeholders to define problems, align on outcomes, and craft thoughtful 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 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, 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
- Access to stock options and a comprehensive benefits plan
- A remote-first team with company paid, in-person socials and the option to work from our Toronto-based office
- Resources to help your professional development, including an L&D budget, performance reviews twice a year and ongoing feedback to ensure you reach your highest potential
- Work with an empathetic, high-performing team in a flexible, results-oriented environment
About PolicyMe:
PolicyMe is a Venture-Backed InsurTech startup on a mission to put families first, protecting them with the honest and uncomplicated life insurance they deserve. Through technology, PolicyMe is streamlining the traditional insurance process, removing barriers and inefficiencies to deliver a fully-underwritten life insurance policy that families deserve but with fewer steps and lower costs.
PolicyMe makes it easy to get a quote and apply for term life insurance online in 20 minutes or less. Since our launch in 2018, we have grown exponentially, selling over $1 billion in life insurance coverage to Canadians.
PolicyMe was also most recently voted as one of Canada’s 50 Most Impactful Companies of 2021, and has been mentioned in BetaKit, National Post, the Global & Mail, Global News and more. If you’re interested in being considered for this opportunity, please submit a resume.
Commitment to Equal Opportunity:
PolicyMe is proud to be an equal opportunity employer. All applicants will be considered for employment without attention to race, colour, religion, sex, sexual orientation, gender identity, national origin, or disability status. We thank all applicants for their interest, however, only those selected for an interview will be contacted.
Accessibility Statement:
PolicyMe is dedicated to ensuring an accessible experience for all candidates. If you require accommodations during the application process, please let us know in the “Additional Information” section of the job application. We are committed to working with you to provide support and make reasonable adjustments throughout the process.
