Founding Advisor, Home

7 days ago

Remote in Toronto, Canada PolicyMe Full time
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 Founding Advisor, Home & Auto to help us build the future of insurance in Canada and beyond.
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 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
  • 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 (including OTE) is $88,000 with earnings potential up to $120,000 CAD. 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 
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. We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.

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