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About the Role
This role is a 12-to-18-month tour, not a career track, focused on solving the company's hardest cross-functional problems and running the planning and decision-making processes. The goal is to build cross-company context before rotating into a product or business owner role, serving as a deliberate pipeline for leadership development.
Responsibilities
- Own the company's hardest cross-functional problems, from framing to execution.
- Take ambiguous, high-stakes problems and drive them across product, growth, ops, and partners.
- Test ideas in the market through scrappy pilots before they earn a roadmap.
- Make data-driven decisions to scale, iterate, or kill pilot initiatives.
- Own the weekly leadership brief, analyzing performance and providing recommendations.
- Lead monthly deep dives into each business line, analyzing performance, experiments, and customer/competitor data.
- Run the quarterly planning cycle, translating founder priorities into actionable options and resource trade-offs.
- Rotate into owning a product line or function within 12 to 18 months.
Requirements
- 4 to 8 years in strategy consulting, investment banking, or strategy/BizOps at a high-growth operating company.
- Exceptional analytical horsepower, including structuring ambiguous problems and performing analysis.
- Proficiency in modeling and SQL, or the willingness to learn quickly.
- Ability to land on a one-page recommendation.
- A proactive 'doer' mentality, preferring to run pilots over perfecting presentations.
- Ability to drive senior stakeholders and cross-functional teams without formal authority.
- Comfort with founders reviewing and challenging work weekly.
- Daily use of AI for research, analysis, and production.
- Understanding of the intense pace, multiple workstreams, and strict weekly rhythm.
- No insurance experience required.
Skills
- Strategy
- Operations
- Problem-solving
- Analytical skills
- Modeling
- SQL
- Stakeholder management
- Cross-functional collaboration
- AI proficiency
- Pilot testing
- Data analysis
- Business planning
Location
- Toronto
- Remote
Work Type
- Remote-first
- Full-time
Experience Level
- Senior individual contributor
Salary/Compensations
- $154,000 to $176,000 CAD
Benefits
- Generous PTO (20 vacation days)
- Comprehensive benefits plan with premiums paid in full
- Investment in professional development
- L&D budget
- AI tooling budget
- Performance reviews twice a year
- Ongoing feedback
- Option to work from home or Toronto-based office
- Costs covered to bring employees in-person twice a year for socials
- Access to stock options based on performance
About the Company
- PolicyMe is Canada's leading digital insurance solution, offering straightforward and affordable financial protection.
- The company's product suite includes Life Insurance, Critical Illness Insurance, and Health & Dental Insurance.
- PolicyMe also offers B2B2C solutions, partnering with organizations.
- Founded by insurance experts and technology entrepreneurs, PolicyMe aims to make insurance simpler and more accessible.
- Since launching in 2018, the company has grown exponentially, selling over $10 billion in insurance coverage.
- PolicyMe operates with a remote-first culture, attracting top talent from across Canada.
- The company fosters a fast-paced, collaborative environment with ambitious yet humble team members.
Equal Opportunity
- PolicyMe is an equal opportunity employer.
- Applicants of all backgrounds are welcome and receive fair consideration regardless of race, colour, religion, sex, sexual orientation, gender identity, national origin, or disability.
- The company is committed to providing an accessible hiring experience and accommodates applicants requiring accommodations during the application process.