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This position was posted on September 25, 2025 and is likely no longer accepting applications. We've kept it here for historical reference. Check out the similar jobs below!
Job Overview
Location
Remote in Toronto
Job Type
Full-time
Category
Product Management
Date Posted
September 25, 2025
Full Job Description
đź“‹ Description
- • Own the end-to-end design lifecycle for high-impact Health & Dental Insurance initiatives during a focused 2-month sprint. You will move from discovery research to pixel-perfect Figma prototypes in days, not weeks, ensuring every screen, micro-interaction, and empty state aligns with PolicyMe’s mission to make insurance refreshingly simple.
- • Conduct lean, tactical research that uncovers real user pain points without slowing momentum. Expect to run 5–8 customer interviews, map critical user journeys, and perform rapid competitive audits, then translate findings into actionable design hypotheses that the squad can test immediately.
- • Partner shoulder-to-shoulder with Product Managers, Engineers, and Growth leads in daily stand-ups and weekly design reviews. You’ll co-define problem statements, scope MVPs, and ruthlessly prioritize features so that every design hour drives measurable improvements in conversion, retention, and customer satisfaction.
- • Optimize existing acquisition and onboarding flows—think landing pages, quote calculators, plan-selection wizards, and checkout—while simultaneously preparing assets for an upcoming product launch. Your work will directly influence how hundreds of thousands of Canadians discover, evaluate, and purchase Health & Dental coverage.
- • Extend and refine PolicyMe’s design system with new components, tokens, and usage guidelines. You’ll balance consistency with innovation, ensuring the system scales gracefully as the product roadmap accelerates.
- • Communicate design rationale with clarity and conviction to both technical and non-technical stakeholders. Expect to present in Monday design critiques, ship async Loom walkthroughs, and document decisions in Notion so context lives on long after the contract ends.
- • Champion accessibility and inclusive design from day one. You’ll audit flows for WCAG 2.2 compliance, recommend copy and color adjustments, and validate solutions with assistive-technology testing—because modernizing insurance means serving every Canadian, regardless of ability.
- • Iterate at startup speed: ship, measure, learn, repeat. You’ll balance speed and craft, releasing polished designs that can be A/B tested within 48 hours, then refining based on quantitative and qualitative feedback loops.
- • Leave behind a playbook. By the end of the contract, you’ll have delivered a concise hand-off package—annotated Figma files, research insights deck, and component documentation—so the team can continue iterating without missing a beat.
🎯 Requirements
- • 5+ years of end-to-end digital product design experience with a portfolio that showcases elegant solutions to complex, regulated, or high-stakes user problems
- • Mastery of Figma for design, prototyping, and design-system management
- • Demonstrated ability to conduct lightweight user research (interviews, surveys, journey mapping) and translate findings into actionable design decisions
- • Proven track record of shipping high-quality UI within tight, 2-week sprint cycles while balancing business goals and user needs
- • Excellent written and verbal communication skills; comfortable presenting to cross-functional stakeholders and defending design rationale with data
🏖️ Benefits
- • Fully remote contract with flexible hours across Canadian time zones
- • Competitive daily rate commensurate with senior-level expertise
- • High-impact, high-visibility work—your designs will reach hundreds of thousands of Canadians within weeks of shipping
- • Direct collaboration with PolicyMe’s leadership team and potential pathway to longer-term engagements or full-time roles
Skills & Technologies
About PolicyMe Inc.
PolicyMe is a Canadian digital life-insurance distributor headquartered in Toronto. Founded in 2018, it uses online underwriting and direct-to-consumer technology to quote, compare and issue term life policies in minutes without commissioned agents, aiming to cut costs and simplify buying coverage. The platform partners with regulated insurers to issue policies, provides licensed advisors for support, and offers a free will-planning tool. Backed by venture capital and regulated by the Canadian Life and Health Insurance Association, PolicyMe serves families across all provinces and territories.
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