Policyme3mo ago

CA$160,000 – CA$180,000/yr

Staff Product Manager (Remote)

In TorontoRemoteFull-timelead

Product ManagementOtherProduct ManagerPrincipal Product ManagerStaff Product Manager

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Quick Summary

Overview

Overview of the Role We’re on a mission to modernize insurance - making it simpler, more accessible, and customer-first. The insurance industry is a $1T market that’s remained largely untouched by the digital revolution, and PolicyMe is here to change that.

Technical Tools

ab-testingagileperformance-managementroadmap-planning

Overview of the Role

We’re on a mission to modernize insurance - making it simpler, more accessible, and customer-first. The insurance industry is a $1T market that’s remained largely untouched by the digital revolution, and PolicyMe is here to change that. As a remote-first, Toronto-based startup with big ambitions, we’re looking for a product leader to help us build the future of insurance in Canada - and beyond.

We are now seeking a Staff Product Manager to join as a leader in our product function. This role will own our post-sale customer experience, our customer account product and critical internal facing products that power how our company operates.

It is a high-impact role that blends analytical thinking, structured execution, and strong collaboration.

Shape our Product Vision:

Evolve our product strategy to improve how our post-sale experience delivers greater customer delight, retention, referral growth and cross-product adoption.

Partner with leadership to develop a compelling vision for how our accounts platform can evolve and set a new standard for how Canadians manage insurance.

Bring the vision to life by building and championing a product roadmap that balances innovation and operational excellence.

Solve Ambiguous Problems:

Develop a deep understanding of both PolicyMe customers and internal customers - use this knowledge to build products and features that your users love.

Take open-ended, unstructured problems and break them down into clearly defined bodies of work.

Come up with creative solutions to solve our most complex problems.

Drive End-to-end Execution and Delivery:

Lead the product team through the full product lifecycle: problem definition, discovery, solution design, scoping, execution, launch, and iteration

Ensure we build the right things, the right way, at the right time - balancing short-term wins with long-term platform evolution.

Collaborate closely with Product Design to build best-in-class customer experiences.

Write clear, actionable product specs that connect business goals, customer needs, and technical constraints.

Partner closely with engineering management to ensure initiatives are well-scoped, appropriately sized, and resilient.

Coordinate go-to-market with Growth, CS, and Operations, ensuring launches are operationally ready and well-supported.

Measurement, Experimentation and Iteration:

Define success metrics and measurement plans for each initiative.

Design and run experiments to validate hypotheses and de-risk larger bets.

Partner with Data to build dashboards, analyze performance, and translate results into next steps — including when to pivot, double down, or sunset work.

Relevant product experience: You have 4-6 years of experience in product management, with experience building customer-facing D2C products and exposure to internal-facing products. You can speak to your track record of leading projects and delivering measurable results.

Exceptional collaboration skills: You have high emotional intelligence and can "be the glue" between many different stakeholders in the organization.

Strong documentation skills: You write clear, concise, and well-informed product specifications/requirements.

Ability to structure ambiguous problems: You have the ability to take an ambiguous problem and structure it. You are someone who can start with an idea and manage it from concept to deployment.

Demonstrated experience leading: You are comfortable bringing people together, leading teams and managing projects with many moving parts. You have a sense of ownership and are excited about driving a project from start to finish.

Strong communication: You know how to tailor your communication style to meet different audiences. You know when to lead conversations, but also when to listen. You know how to set expectations with different stakeholders and when to ask these stakeholders for help. You can take a complex topic and explain it succinctly in an easy-to-understand manner.

A strong sense for prioritization: You know how to prioritize different builds and define what is truly part of an MVP to optimize developer productivity. You know how to balance agile market feedback with our customers' product expectations.

Curiosity and comfort with technical topics: While you do not need a technical background, you are naturally curious about how everything works. You know when to ask clarifying questions and are not shy about diving into complex topics.

An analytical mindset: You are comfortable working with product data, defining its structure and running analyses to answer key questions.

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 $160,000–$180,000 CAD, based on experience. We’ll walk through the details together during the interview.

Location & Eligibility

Where is the job

Worldwide

Fully remote, anywhere in the world

Who can apply

Same as job location

Listed under

Worldwide

Listing Details

Posted: January 16, 2026
First seen: March 26, 2026
Last seen: May 11, 2026

Posting Health

Days active: 45
Repost count: 0
Trust Level: 51%
Scored at: May 11, 2026

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Policyme

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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

policyme.com

Jobs

View 11 jobs

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Salary

CA$160,000 – CA$180,000

per year