Remote Life Insurance Customer Success Pro

PolicyMe; Toronto; Hybrid; CAD 55,000 - 66,000; Full time

Benefits offered by this job

20 days PTO

Comprehensive benefits paid by Policy

L&D budget & AI tooling budget

Performance reviews & ongoing feedback

Remote-first with annual in-persons

Stock options

In-person meetups twice a year

Job summary

PolicyMe, a remote-first Canadian startup, is seeking a Customer Success Specialist to support clients and the Advisor Team throughout the life insurance journey. You will manage policy servicing tasks, client communication, and help deliver an exceptional experience across Canada and beyond.

Standard hours are 9:00 a.m. – 5:00 p.m. ET, with flexibility for Pacific Time. Compensation targets CAD 55k–66k plus stock options and strong benefits.

Qualifications

• 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.

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.

Skills

Communication

English proficiency

Multi-system familiarity

Attention to detail

Empathy

Integrity

Proactive mindset

Tools

HubSpot

Front

Job description

PolicyMe, a remote-first Canadian startup, is seeking a Customer Success Specialist to support clients and the Advisor Team throughout the life insurance journey. You will manage policy servicing tasks, client communication, and help deliver an exceptional experience across Canada and beyond.

Standard hours are 9:00 a.m. – 5:00 p.m. ET, with flexibility for Pacific Time. Compensation targets CAD 55k–66k plus stock options and strong benefits.