Strategy & Operations Manager

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 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.

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 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. 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/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.

About PolicyMe:

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. Founded by a team of insurance experts and technology entrepreneurs, PolicyMe is committed to making insurance simpler and more accessible. Since our launch in 2018, we have grown exponentially, selling over $10 billion in insurance coverage to Canadians.

We are proud of the team we’ve built and are excited for those that are yet to join us. We operate with a remote-first culture, attracting top talent from across Canada. If you’re looking for a fast-paced, collaborative environment, working alongside incredibly ambitious yet humble humans, we may be the right place for you! To learn more, visit www.policyme.com.

Additional Notes:

• Job Vacancy: This role reflects growth in our team and expanded operational scope. We’re hiring to support increasing demand and continue delivering an exceptional customer experience.
• Commitment to Equal Opportunity: PolicyMe is an equal opportunity employer. We welcome applicants of all backgrounds and provide fair consideration regardless of race, colour, religion, sex, sexual orientation, gender identity, national origin, or disability.
• Accessibility Statement: We are committed to providing an accessible hiring experience. If you require accommodations during the application process, please indicate this in the “Additional Information” section of your application.

We thank all applicants for their interest, however, only those selected for an interview will be contacted.