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 Home & Auto Insurance Advisor to help us build the future of insurance in Canada and beyond.
As a Home & Auto Insurance Advisor, you’ll be on the front lines helping customers protect their homes and vehicles while delivering a modern, digital-first experience. You’ll focus on sales execution - handling inbound leads, closing business, and providing clear, honest advice that builds long-term trust with our customers. You’ll also collaborate with the rest of the team to refine our sales processes, share insights from customer conversations, and contribute to the continued growth of PolicyMe’s P&C business.
Reports To: Director of Sales
What you'll be doing
- First 6 months:
- Educate prospective customers on Home & Auto insurance options using PolicyMe’s digital platform and your product expertise, breaking down coverage in clear, honest terms so they feel confident moving forward.
- Manage a high-volume, inbound pipeline of Home & Auto leads, moving them efficiently through the sales funnel and converting qualified opportunities into closed policies via phone, SMS, and email.
- Use HubSpot to track every touchpoint - calls, emails, follow-ups, and deal stages - so your pipeline is always clean, up to date, and easy to forecast from.
- Recommend the right coverage based on customer needs using a consultative, customer‑first approach that balances protection, price, and eligibility.
- Build and refine sales scripts, talk tracks, objection‑handling, workflows, and follow‑up sequences in HubSpot to improve contact rates, appointment show rates, and close rates.
- Set the tone and standards for how PolicyMe serves P&C customers by delivering a high‑energy, high‑conversion, but always honest and customer‑centric experience on every interaction.
- Ensure all recommendations and customer interactions are fully compliant with RIBO requirements, carrier guidelines, and internal policies.
- 6–12 months and beyond:
- Establish yourself as a top‑performing Home & Auto advisor, consistently hitting and exceeding monthly sales and activity targets (contact rate, talk time, conversions etc).
- Continuously optimize your own sales process by testing new hooks, discovery questions, and follow‑up cadences - and feeding winning approaches back into team playbooks.
- Contribute to a scalable, repeatable sales playbook for Home & Auto by logging accurate data in HubSpot, surfacing common objections, and helping refine qualification criteria and next‑best actions.
- Identify and act on bundle and cross‑sell opportunities with Life and Health & Dental, increasing overall premium per household while keeping customer needs and affordability front and center.
- Help position PolicyMe as Canada’s go‑to digital‑first distributor of personal insurance by delivering an experience that feels modern, simple, and genuinely sales‑driven in the best sense: efficient, helpful, and outcome‑oriented.
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), ideally in a high‑volume, phone‑based or digital sales environment.
- A builder mentality - entrepreneurial and adaptable - with a track record of not just working a process but improving it (scripts, sequences, qualification, and follow‑up).
- A proven track record of exceeding sales targets in a consultative sales environment, with comfort owning a full inbound pipeline from first contact to close.
- Strong pipeline management and organization skills: you’re comfortable juggling a large volume of leads while maintaining tight follow‑up discipline and clean CRM hygiene.
- Strong communication skills and a consultative sales style - you can manage objections, explain complex coverage concepts clearly, and make clients feel heard while still driving to a decision.
- High empathy and discretion, especially when discussing personal and financial details, paired with a clear sense of urgency and ownership over your numbers.
- Comfort with CRM and workflow tools (HubSpot preferred) and a willingness to lean into data, playbooks, and feedback to continuously improve performance.
- High ethical standards and a commitment to compliance, confidentiality, and always putting the customer’s best interests first - even while you’re chasing ambitious sales goals.
- Experience at a digital‑first distributor is an asset.
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 $88,000–$120,000 CAD, based on experience. 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
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.
