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 Growth Strategy Lead to help us build the future of insurance in Canada and beyond.
We're now seeking a GTM Strategy Lead to own go-to-market strategy across our product portfolio – Life & Critical Illness, Health & Dental, and Home & Auto. Our growth engine is strong and getting stronger; as we expand into new customer segments and launch new products, this role figures out how we win each one: who the customer is, what they need to hear, and where to reach them profitably. This is a pivotal senior individual-contributor role, reporting to the VP of Growth and working closely with teams across the organization.
Please note: While we're a remote-first company, for this role we're looking for candidates who are based in the Greater Toronto Area.
What you'll be doing:
Own Go-to-Market Strategy for New Audiences & Products
Develop the go-to-market strategy for our newest opportunities – new customer segments, newly launched product lines, and future partner launches.
Build deep customer and market understanding through primary research: customer conversations, advisor call reviews, funnel data, and competitive pricing analysis.
Own the go-to-market strategy for new and existing customer segments, determining who we target, how we win, and what drives profitable growth, while partnering with cross-functional teams to bring that strategy to market.
Define which customer segments we can win profitably, and prioritize where we invest.
Drive Hands-on Execution & Experimentation
This is not a slide-deck role – you'll personally run the analysis, write the positioning, and get into the weeds of campaigns alongside our channel teams.
Design and run go-to-market experiments with a dedicated test budget: validate segments, messages, and channels at small scale before we invest at volume.
Make clear calls on what to scale, iterate, or kill – backed by data.
Build playbooks from what works so the broader team can run them, then move to the next opportunity.
Sharpen Our Core Engine
Strengthen the positioning and point of view across our highest-performing product line, working closely with our content and paid teams.
Bring the voice of the customer into how we market – grounded in research, not assumptions.
Partner Across the Business
Coordinate launch readiness with Product, Sales, and Operations so new products ship with go-to-market behind them.
Over time, build context on our B2B2C partner programs to support future partner launches.
What we are looking for:
4–6 years in strategy consulting, investment banking, growth/strategy at a high-growth startup, or brand/category management at a top CPG – ideally with some operating experience at a startup or scale-up.
Exceptional analytical horsepower: you structure ambiguous problems, build the analysis yourself, and turn it into a clear recommendation. A track record of solving hard problems and grinding until they're solved matters more than direct experience in this exact job.
Strong instinct for customers: you'd rather talk to ten customers than build a model on assumptions – but you can build the model too.
A doer. You're energized by rolling up your sleeves in a company where there's no one to delegate to.
AI-native: you use AI daily to research, analyze, and produce faster – and you raise the bar for how a team works with it.
Comfortable owning a number and being measured against it every quarter.
Strong communicator who can align executives, channel owners, and product teams behind a direction.
No insurance experience required – we'll teach you the industry; you bring the curiosity and the work ethic.
Why join us:
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 $140,000–$155,000 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.
