Customer Success Specialist

Customer Success Specialist

Location: Remote-first (Toronto-based startup)

About PolicyMe

PolicyMe is on a mission to modernize insurance, making it simpler, more accessible, and customer-first. As Canada’s leading digital insurance solution, we offer straightforward and affordable financial protection, including Life, Critical Illness, and Health & Dental Insurance. Founded in 2018 by insurance and tech experts, we've already sold over $10 billion in coverage. We foster a fast-paced, collaborative, and remote-first culture, attracting top talent across Canada to disrupt a $1T industry.

About the Role

As a Customer Success Specialist, you will be crucial in supporting our customers and Advisor Team throughout the life insurance journey. You’ll be responsible for policy servicing tasks, client communication, and helping us deliver an exceptional customer experience every step of the way. Standard working hours are 9:00 a.m. to 5:00 p.m. Eastern Time, with flexibility to support Pacific Time hours as business needs evolve.

Key Responsibilities

• Manage a caseload of in-progress applications through the underwriting process.
• Navigate tools like HubSpot and Front to complete daily task queues.
• Coordinate and follow up on medical exam bookings with vendors and clients.
• Order and track underwriting requirements (e.g., APS, MVRs).
• Handle inbound calls and respond to client emails.
• Track missed payments and help clients update billing info.
• Report underwriting decisions to the Medical Information Bureau (MIB).
• Process policy change requests (address updates, beneficiary changes).
• Maintain accurate records and submit the weekly MIB report.
• Collaborate cross-functionally with Advisors, QA, Sales, and Customer Service.
• Offer feedback and participate in process/tooling improvement discussions.

What You'll Bring

• 1–2 years of experience in insurance, customer service, or call center roles.
• Strong verbal and written communication in English.
• Comfortable using multiple systems and learning new tools quickly.
• Excellent attention to detail and ability to multitask in a fast-paced environment.
• Empathy, patience, and a natural drive to go above and beyond for customers.
• Integrity and reliability - someone who takes pride in doing things right.
• A proactive mindset and openness to giving and receiving feedback.

Why PolicyMe?

• 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 & Benefits

• Total Target Cash Compensation: $55,000–$66,000 CAD, based on experience.
• Comprehensive benefits plan with premiums paid in full.
• Stock options based on performance.

Additional Information

• Job Vacancy: This role reflects growth in our team and expanded operational scope, supporting increasing demand and delivering exceptional customer experience.
• Commitment to Equal Opportunity: PolicyMe is an equal opportunity employer, welcoming applicants of all backgrounds. We provide fair consideration regardless of race, colour, religion, sex, sexual orientation, gender identity, national origin, or disability.
• Accessibility Statement: We are committed to 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.