Strategy & Operations Manager

Own the company's hardest cross-functional problems

• 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.
• Problems span new product and segment expansion, go-to-market for launches, partner programs, and the operational constraints slowing us down.

Test ideas in the market before they earn a roadmap

• Run the scrappy pilot before anything gets built: validate a segment, a message, or a new motion at small scale with whatever tools get it done.
• 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.

Run how the company plans and decides

• 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

Become a line owner

• All of the above is the fastest route to the context this business demands: customer experience, pricing strategy, distribution strategy, customer acquisition, product development.
• Within 12 to 18 months, rotate into owning a product line or function. Your work on programs and deep dives is what that decision is based on.

• 4 to 8 years in strategy consulting, investment banking, or strategy/BizOps at a high-growth operating company.
• Exceptional analytical horsepower: you structure ambiguous problems, do the analysis yourself (strong modeling; SQL or the willingness to learn it fast), and land on a recommendation in one page, not ten.
• A doer. 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.
• AI-native: you use AI daily to research, analyze, and produce faster, and you raise the bar for how a team works with it.
• Clear-eyed about the trade: the pace is intense, several workstreams run at once, and the weekly rhythm does not slip. In exchange you get the steepest learning curve here and the fastest credible route to running a business line.
• No insurance experience required. We'll teach you the industry; you bring the curiosity and the work ethic.

• 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 $154,000 to $176,000 CAD, based on experience. We'll walk through the details together during the interview.