Overview of the role
Join us at PolicyMe! We’re modernizing insurance and we’d like your help. The Canadian P&C insurance landscape has remained largely unchanged for decades and we are in the process of changing that. We’re a remote-first, Toronto-based startup with big ambitions. PolicyMe is seeking a motivated, entrepreneurial Founding Home & Auto Insurance Advisor to join our team.
This is a unique opportunity: as our first P&C sales hire, you’ll be on the front lines helping customers protect their homes and vehicles while also shaping the future of PolicyMe’s P&C business. In the early months, you’ll be focused on sales execution: handling inbound leads, closing business, and proving out our playbook. From there, you’ll play a central role in scaling the business – building sales systems, mentoring new advisors, and helping define our broader strategic roadmap for P&C.
Reports To: Director of Sales
Salary Range: Competitive base + commission + equity potential
What you’ll be doing:
- First 6 months
- Educate customers on Home & Auto insurance options using PolicyMe’s digital platform and your product expertise.
- Manage the first cohort of inbound leads, closing sales with a consultative, customer-first approach.
- Build and refine sales scripts, workflows, sales process and follow-up sequences in HubSpot.
- Collaborate with RevOps and the Director of Sales to build and refine sales systems that enable consistency, efficiency, and high performance at scale.
- Provide structured feedback to our Product team to improve the digital journey.
- Set the tone and standards for how PolicyMe serves P&C customers.
- 6–12 months and beyond
- Scale yourself: transition into a leadership role by mentoring and onboarding new advisors.
- Develop and refine a scalable, repeatable sales playbook that enables every advisor to reach their full potential.
- Coach and train the team to consistently hit (and exceed) targets.
- Collaborate with marketing and growth to align lead quality and conversion strategies.
- Contribute directly to the strategic roadmap for P&C, including bundling and cross-sell opportunities with Life and Health & Dental.
- Help position PolicyMe as Canada’s go-to digital-first distributor of personal insurance.
What we are looking for:
- A licensed P&C advisor in Ontario (RIBO Level 1 or higher).
- 3+ years of experience selling personal lines (home & auto).
- Builder mentality — someone who is entrepreneurial, adaptable, and motivated to create something from the ground up.
- Demonstrated success hitting or exceeding sales targets in a fast-paced environment.
- Comfort with CRM and workflow tools (HubSpot preferred).
- Strong communication skills and a consultative sales style.
- Experience at a digital-first distributor (e.g., direct-to-consumer broker, carrier, or insurtech) is an asset.
- Nice-to-have: prior experience mentoring, coaching, or leading other advisors.
- Please note: As a standard procedure for audit compliance, this position is subject to credit checks, background checks, and reference checks.
Why join us:
- Generous PTO – 20 vacation days
- Access to stock options and a comprehensive benefits plan
- A remote-first team with company paid, in-person socials and the option to work from our Toronto-based office
- Resources to help your professional development, including an L&D budget, performance reviews twice a year and ongoing feedback to ensure you reach your highest potential
- Work with an empathetic, high-performing team in a flexible, results-oriented environment
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.
Commitment to Equal Opportunity:PolicyMe is proud to be an equal opportunity employer. All applicants will be considered for employment without attention to race, colour, religion, sex, sexual orientation, gender identity, national origin, or disability status. We thank all applicants for their interest, however, only those selected for an interview will be contacted.
Accessibility Statement:PolicyMe is dedicated to ensuring an accessible experience for all candidates. If you require accommodations during the application process, please let us know in the “Additional Information” section of the job application. We are committed to working with you to provide support and make reasonable adjustments throughout the process.
