We’re on a mission to modernize insurance, making it simpler, more accessible, and customer-first. The insurance industry is a $1T market that has 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 Strategy & Operations Manager to help us build the future of insurance in Canada and beyond.

You build more cross-company context than almost anyone at PolicyMe, then rotate into a product or business owner seat (PM, GM, functional lead), with placements decided by the VP of Growth, CEO, and COO. we’re now running it as a deliberate pipeline. This is a senior individual-contributor role reporting to the VP of Growth. Take an ambiguous, high-stakes problem from framing to answer to execution: a one-page case with a recommendation, a decision from leadership, then driving the work across product, growth, ops, and partners.

Test ideas in the market before they earn a roadmap Make the call to scale, iterate, or kill based on what the pilot showed, then hand proven work to a product team with a framed brief and take the next problem.

Own the weekly leadership brief: performance across every product line, the decisions leadership needs to make, and a recommendation for each. Your analysis is what the founders read every Wednesday.

Lead monthly deep dives into each business line: funnel performance, live experiments, customer and competitor evidence, and what we do differently next month. You’ll build these with the line leads, which means you’ll know every business here from the inside.

Run the quarterly planning cycle:



turn founder priorities into a sized set of options and put the real resource trade-offs in front of leadership All of the above is the fastest route to the context this business demands: customer experience, pricing strategy, distribution strategy, customer acquisition, product development.

Exceptional analytical horsepower: you structure ambiguous problems, do the analysis yourself (strong modeling; SQL or the willingness to learn it quick), and land on a recommendation in one page, not ten. ~ You’d rather run the pilot than polish the deck, and you’re energized by a company where there’s no one to delegate to. ~ You can drive senior stakeholders and cross-functional teams without formal authority, and you’re comfortable having founders read and challenge your work weekly. ~ In exchange you get the steepest learning curve here and the fastest credible route to running a business line. ~ No insurance experience required. Generous PTO – 20 vacation days 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 $154,000 to $176,000 CAD , based on experience. 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. We operate with a remote-first culture, attracting top talent from across Canada.

We’re hiring to support increasing demand and continue delivering an exceptional customer experience. We welcome applicants of all backgrounds and provide fair consideration regardless of race, colour, religion, sex, sexual orientation, gender identity, national origin, or disability. We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information.

These tools assist our recruitment team but do not replace human judgment. If you would like more information about how your data is processed, please contact us. #

📌 Remote Strategy & Operations Manager (Quebec City)
🏢 Bilinguallink
📍 Quebec City