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.
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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
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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 [http://www.policyme.com/].
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.
