About this role.
PolicyMe is seeking a Growth Marketing Specialist to own lifecycle marketing strategy and execution across acquisition, onboarding, retention, re-engagement, and cross-sell journeys. The role centers on building personalized CRM workflows, segmentation, trigger logic, email modules, and templates, with HubSpot specifically referenced. The specialist will run A/B tests, analyze performance, and partner closely with Product, Growth, Design, Data, and Customer Experience teams. It is a remote-first Canadian startup role suited to a systems-minded marketer with strong customer-centric writing and AI-enabled workflow skills.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
4/5Pace & Pressure
4/5Autonomy Level
4/5Communication Load
4/5Salary analysis
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Core skills
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Cover letter sample
Dear Hiring Team,
I am excited to apply for the Growth Marketing Specialist role at PolicyMe. My lifecycle marketing experience includes building customer journeys, audience segmentation, automated CRM workflows, and measurable experimentation that improves conversion and retention. I would bring a systems-oriented, customer-first approach to creating scalable HubSpot programs and partnering effectively with Product, Design, Growth, Data, and Customer Experience teams. I am particularly drawn to PolicyMe’s mission to make insurance more accessible for Canadians and would welcome the opportunity to help deliver high-impact customer experiences.
Sincerely,
[Your Name]
Sample interview questions
I would begin by defining the customer segment, desired behavior, success metric, and key constraints. I would map the journey stages and decision points, build the required event, enrollment, suppression, and branching logic, then QA the workflow with test records before launch. After launch, I would monitor delivery, engagement, conversion, and downstream retention metrics and iterate based on a documented test plan.
I prioritize tests by potential business impact, confidence in the hypothesis, implementation effort, and learning value. For example, I might test onboarding timing, message framing, CTA placement, or segmentation rules, while keeping a clear primary metric such as activation or conversion. I ensure tests have sufficient audience size and document results so winning insights can be reused across programs.
I use behavioral and profile data to create meaningful segments, then define explicit entry criteria, exclusions, frequency controls, and exit conditions. I would also account for edge cases such as customers changing products, completing a target action early, or receiving overlapping campaigns. This protects the customer experience while making the automation reliable at scale.
I would partner with Product and Data to identify the relevant events, customer states, and success outcomes, and with Design and Growth to align creative, channel, and launch timing. Before release, I would establish ownership, timelines, tracking requirements, and a reporting cadence. This shared plan reduces implementation gaps and makes campaign performance easier to assess.
I use AI to accelerate ideation, draft variants, summarize research, and improve workflow documentation, but I retain human accountability for strategy, factual accuracy, compliance, brand voice, and customer empathy. For customer-facing communications, I review outputs carefully, validate claims, and test performance rather than assuming generated copy is effective. AI is most valuable when paired with clear prompts, strong guardrails, and measurable feedback loops.
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 Marketing Specialist to help us build the future of insurance in Canada and beyond.
As our Growth Marketing Specialist, you’ll own the strategy and execution of customer lifecycle marketing across multiple touchpoints, helping customers get the right message at the right time. You’ll partner closely with Product, Growth, Design, Data, and Customer Experience teams to build personalized journeys that improve engagement, conversion, retention, and cross-sell opportunities. This is an exciting opportunity to shape how millions of customer interactions are delivered while driving measurable business impact through experimentation, automation, and data-driven decision making.
What you’ll be doing:
- Design customer journeys across the full lifecycle, from acquisition and onboarding through retention and re-engagement.
- Continuously test, measure, and optimize campaigns through A/B testing and performance analysis.
- Design email and lifecycle assets using AI (Claude), then build them as modules and templates in HubSpot.
- Build and maintain the workflows that power our customer journeys — enrolment logic, triggers, branching, segmentation to deliver highly personalized customer experience.
- Partner with Product, Growth, Design, and Data teams to launch campaigns supporting new products, features, and business initiatives.
- Monitor lifecycle performance metrics and identify opportunities to improve customer engagement, conversion, retention, and lifetime value.
- Help grow lifecycle marketing into a scalable function as PolicyMe expands.
What we’re looking for:
- 2-3+ years of experience in growth marketing, product marketing, customer marketing, lifecycle marketing, or similar marketing roles within a fast-paced technology company, agency, or consumer brand.
- You’re systems thinker. You enjoy breaking down complex customer journeys into scalable workflows. You naturally think through dependencies, edge cases, and customer scenarios, and take satisfaction in building systems that work reliably at scale.
- You have strong written communication skills with an eye for customer-centric messaging. You can tell the difference between copy that serves the customer and copy that serves us.
- You’re eager to build from scratch and figure things out. You find real satisfaction in a process you’ve built well and an experience you’ve created — the kind of person who’s energized by a blank slate, not daunted by it.
- You’re AI-literate, with a proven track record of solving problems and optimizing your work with AI.
Nice To have:
- Experience with lifecycle marketing platforms such as Braze, Iterable, Customer.io, HubSpot, Salesforce Marketing Cloud, or similar CRM tools.
- French speaking
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 $80,000–$105,000 CAD, based on experience. We’ll walk through the details together during the interview.
Compensation
Additional Information
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.
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