Job Overview
Location
Remote in Toronto
Job Type
Full-time
Category
Sales
Date Posted
March 26, 2026
Full Job Description
đź“‹ Description
- • As a Business Development Representative at PolicyMe Inc., you will play a pivotal role in modernizing the insurance industry by connecting with prospective customers who have shown initial interest through quote requests, started applications, or approved policies, helping them progress toward completing their coverage and contributing to the company’s mission of making insurance simpler, more accessible, and customer-first in a largely untapped $1T market.
- • You will manage a balanced mix of inbound and outbound engagement, focusing on converting incomplete applications into completed policies, re-engaging stalled leads in the sales funnel, and qualifying new clients to ensure a steady flow of high-intent opportunities for the advisory team.
- • Your day-to-day responsibilities will include initiating contact with inbound leads via phone, email, and digital channels, conducting discovery conversations to understand customer needs, educating prospects on PolicyMe’s offerings, and guiding them through the application process to reduce drop-off and increase conversion rates.
- • You will actively re-engage dormant leads by identifying reasons for stagnation, providing timely follow-ups, addressing objections, and leveraging personalized outreach strategies to revive interest and move prospects back into active consideration.
- • A key part of your role will involve scheduling and confirming high-quality meetings between qualified leads and licensed Insurance Advisors, ensuring advisor calendars are optimized with productive, well-prepared conversations that increase the likelihood of policy issuance.
- • You will collaborate closely with the Business Development and Marketing teams to test and refine outreach scripts, messaging sequences, and engagement tactics, using data and customer feedback to iterate on best practices and improve overall funnel efficiency.
- • By participating in ongoing experiments and A/B tests, you will contribute insights that help codify successful strategies, scale proven methods, and enhance the effectiveness of PolicyMe’s lead conversion engine across channels.
- • You will maintain accurate records of all interactions in the CRM, track key performance indicators such as response rates, conversion rates, and meeting show-up percentages, and use this data to self-optimize your approach and support team-wide improvements.
- • Success in this role demands a proactive, curious, and resilient mindset — you will be expected to adapt quickly based on real-time feedback, embrace experimentation, and continuously refine your communication and persuasion techniques to better serve diverse customer profiles.
- • Top performers will have a clear pathway to pursue insurance licensing and transition into a licensed Insurance Advisor role, enabling long-term career growth within PolicyMe’s expanding advisory team as the company scales its operations nationally and beyond.
- • You will join a remote-first, Toronto-based startup culture that values innovation, agility, and customer obsession, where your contributions directly influence how the company evolves its go-to-market strategy in a traditionally slow-to-change industry.
- • Working at PolicyMe means being part of a mission-driven team that is leveraging technology and thoughtful design to disrupt legacy insurance models, offering you the opportunity to build meaningful expertise in insurtech while developing transferable skills in sales, customer psychology, and funnel optimization.
🎯 Requirements
- • Proven experience in business development, sales development, or customer-facing roles with a track record of engaging leads, managing pipelines, and driving conversion in B2C or B2B environments.
- • Strong communication and interpersonal skills, with the ability to build rapport quickly, listen actively, and convey complex information in a clear, empathetic, and persuasive manner across phone and digital channels.
- • Proficiency with CRM software (e.g., HubSpot, Salesforce) and sales engagement tools, combined with a data-minded approach to tracking activity, analyzing performance, and iterating on outreach strategies.
- • Self-motivated, organized, and able to thrive in a remote-first startup environment, demonstrating initiative, accountability, and the ability to manage time effectively without direct supervision.
- • Familiarity with the Canadian insurance landscape or a strong willingness to learn about life insurance products, underwriting basics, and regulatory considerations relevant to customer conversations.
- • Growth mindset and resilience — comfortable with experimentation, feedback, and iteration, viewing rejection as data and using insights to improve future engagement.
🏖️ Benefits
- • Fully remote work arrangement with flexibility to operate from anywhere in Canada, supported by a collaborative virtual culture that emphasizes connection, inclusion, and work-life balance.
- • Competitive base salary combined with performance-based bonuses tied to individual and team metrics, rewarding consistency, initiative, and impact on funnel conversion and revenue generation.
- • Comprehensive health and wellness benefits, including extended medical, dental, vision, and mental health support, reflecting PolicyMe’s commitment to employee well-being as a core value.
- • Opportunities for professional development and career advancement, including sponsorship for insurance licensing exams and a clear path to transition into a licensed Insurance Advisor role for high performers.
- • Access to modern tech tools and a supportive team environment that encourages learning, experimentation, and knowledge sharing, enabling you to grow your skills in sales technology, customer psychology, and funnel optimization.
- • Equity participation through stock options, allowing you to share in the long-term success of a fast-growing insurtech startup with ambitious plans to transform insurance in Canada and beyond.
Skills & Technologies
Remote
About PolicyMe Inc.
PolicyMe is a Canadian digital life-insurance distributor headquartered in Toronto. Founded in 2018, it uses online underwriting and direct-to-consumer technology to quote, compare and issue term life policies in minutes without commissioned agents, aiming to cut costs and simplify buying coverage. The platform partners with regulated insurers to issue policies, provides licensed advisors for support, and offers a free will-planning tool. Backed by venture capital and regulated by the Canadian Life and Health Insurance Association, PolicyMe serves families across all provinces and territories.
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