Remote Strategy & Operations Manager

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 Policy Me 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.

Strategy & Operations is a new team with an exciting mandate: work directly with the VP of Growth and the founders on the questions that decide the company’s trajectory, and run the process by which the company plans, reviews, and decides. How do we grow volume and margin at the same time? Which product lines and segments do we expand into next, and in what order?

Where are we spending resources that we shouldn’t be?

The role is a 12-to-18-month tour, not a career track. You build more cross-company context than almost anyone at Policy Me, then rotate into a product or business owner seat (PM, GM, functional lead), with placements decided by the VP of Growth, CEO, and COO. The generalist-to-owner path is how several of our strongest leaders got here; we’re now running it as a deliberate pipeline.

This is a senior individual-contributor role reporting to the VP of Growth.

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/Biz Ops 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,…