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 People & Culture Generalist to help us build the future of insurance in Canada and beyond.
As our People & Culture Generalist, you’ll be at the center of our People team - you’ll own key processes and systems that ensure all our humans have a great employee experience from their first day to their last! You’ll support and improve our people programs across onboarding, performance, engagement, and day-to-day people operations. This is a great opportunity for someone who is extremely accountable, can work quickly but with intention, and cares deeply about building thoughtful experiences that help humans and teams perform at their best.
What you'll be doing:
- Manage all employee data within our People systems including onboarding, role changes, promotions, terminations and more — all with a focus on accuracy.
- Own our onboarding and offboarding experiences, partnering closely with IT and Finance.
- Support execution of performance reviews, engagement surveys, and company-wide people programs, including coordination, communications, and reporting.
- Own coordination with our benefits provider and ensure employees are maximizing our program.
- Fully own our company social events, including the planning and execution of our in-person company events (we bring our company together twice a year!), virtual and team events.
- Manage our office - while we are remote-first, we have an office in downtown Toronto that many of us frequent on Thursdays. You’d be responsible for all support / coordination of office activities.
- Annual gifting coordination, helping think through what will bring the most joy to our employees to celebrate the year and executing on the vision.
- Serve as a trusted point of contact for employees and managers on HR inquiries.
- Help deliver and continuously improve core people programs such as performance reviews, engagement initiatives, learning and development, and team culture initiatives.
- Own metrics and reporting across all the areas you’re responsible for.
- Support time sensitive projects and requests from the VP, People & Culture
What we are looking for:
- 3+ years of experience in an HR, People Operations, or People & Culture role, ideally in a fast-paced startup or high-growth environment.
- Strong knowledge of core HR practices across employee lifecycle management, people operations, and compliance.
- Experience supporting people programs such as onboarding, performance management, engagement, and policy administration.
- Someone with a ‘yes, I can help’ attitude, who will be there to support our People team as well as all our employees.
- Highly organized with strong attention to detail and the ability to manage multiple priorities at once.
- Strong interpersonal and communication skills, with the ability to build trust across teams and levels.
- Comfortable working with HR systems, documentation, and process improvement.
- Sound judgment and discretion when handling sensitive and confidential information.
- Nice to have: Experience using AI tools and workflow automations to improve efficiency, streamline processes, and support better decision-making.
- Must be located in Toronto and willing to work in-office 1-2 days per week.
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 $71,500–$88,000 CAD, based on experience. We’ll walk through the details together during the interview.
Skills Required
- 3+ years of experience in HR, People Operations, or People & Culture
- Strong knowledge of core HR practices
- Experience with onboarding and performance management
- Organized with strong attention to detail
- Strong interpersonal and communication skills
- Experience using AI tools (nice to have)
What We Do
We are on a mission to put families first with simple and affordable insurance. We strongly believe that life insurance is fundamental to a sound financial plan. It ensures that your family can replace lost income to pay for key expenses, eliminate debt, pay for college, or address other financial goals in the unfortunate circumstance that you pass. However, we also understand that life insurance is complicated. There are many factors to take into account in determining how much life insurance is right for you, and what type of policy best suits your needs. That is why we believe life insurance advice should be transparent, customized and most importantly, convenient. We are an experienced team trying to change the insurance industry with a customer first approach. Our proprietary life insurance algorithm assesses your needs and recommends the best product for you – regardless of commission structure. Life insurance is complicated, and our advice engine can help you find the the best protection in the most cost-effective way





