Policyme26d ago

Senior Product Designer (Remote)

Ontario · (ontario) · OntarioRemoteFull-timesenior

Design & CreativeProduct Designer

0 views0 saves0 applied

Apply Now

Quick Summary

Overview

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,

Technical Tools

Design & CreativeProduct Designer

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.

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.

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.

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.

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.

Listing Details

Posted: March 30, 2026
First seen: March 30, 2026
Last seen: April 26, 2026

Posting Health

Days active: 26
Repost count: 0
Trust Level: 39%
Scored at: April 26, 2026

Signal breakdown

freshnesssource trustcontent trustemployer trust

Apply for this position

Policyme

lever

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.

Employees

125

Founded

2018

Domain

Jobs

External application · ~5 min on Policyme's site

Please let Policyme know you found this job on Jobera.