Overview of the roleWe'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.
