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 Product Design Contractor to help us on a short-term project within our Health and Dental Insurance product team. You’ll play a hands-on role in designing and refining customer journeys and core flows. This contract is focused on immediate, high-impact contributions - with the potential for further collaboration / FT opportunities down the line.
This role will require Full-Time hours for 2 months.
What you will be doing:
- Delivering design work end-to-end: research, wireframes, prototypes, usability testing, and polished high-fidelity designs.
- Running focused, lightweight research to quickly surface customer insights (interviews, journey mapping, competitor reviews).
- Partnering closely with product managers, engineers, and stakeholders to define problems and ship solutions that balance usability with business needs.
- Supporting key initiatives such as optimizing existing flows, refining landing pages, or contributing to upcoming launches.
- Using our design system to keep work consistent and scalable, while suggesting improvements and creating new components where needed where needed.
- Participating in essential team check-ins (design reviews, stand-ups, retros) to stay aligned and keep projects moving.
- Clearly communicating design choices and progress, keeping stakeholders in the loop as you work.
- Balancing speed and quality - delivering quickly while iterating based on feedback.
What we are looking for:
- 5+ years of experience designing digital products with a strong portfolio that demonstrates elegant solutions to complex problems.
- Strength in visual design, interaction design, and information architecture.
- Experience moving quickly from research to design to iteration.
- Ability to gather or synthesize user insights to inform decisions.
- Comfort working in Figma and with existing design systems.
- Strong communication skills—you can explain your thinking and align with both designers and non-designers.
- A flexible, pragmatic approach—able to deliver high-impact design in a short time frame.
We’re looking for a contractor who is collaborative, adaptable, and comfortable jumping into a fast-moving team to deliver immediate value.
Why join us:
- Be part of a fast-moving startup that’s modernizing insurance in Canada.
- Work on meaningful projects with immediate impact on customer experience and business outcomes.
- Collaborate with an empathetic, high-performing team that values clear communication, ownership, and results.
- Gain exposure to a cross-functional environment, working alongside Product, Growth, and Engineering leaders.
- Flexibility to work remotely from anywhere in Canada!
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.
