Customer Success Specialist (Remote)

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 Customer Success Specialist to help us build the future of insurance in Canada and beyond.

As a Customer Success Specialist, you will support 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.

What you’ll be doing

• 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 we are looking for

• 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 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 $55,000–$66,000 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

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.