Customer Success Specialist
Job Description
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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
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PolicyMe
View Company ProfilePolicyMe is a rapidly growing Canadian InsurTech company that is fundamentally disrupting the traditional life insurance industry. Founded in 2018 and headquartered in Toronto, Ontario, the company was built to strip away the complexity, hidden fees, and aggressive upselling of legacy insurance brokers. Under the hood, PolicyMe operates a fully digital, direct-to-consumer platform offering highly affordable term life and critical illness insurance. By leveraging advanced algorithmic underwriting, the platform can process applications in real-time, granting instant approvals to the majority of users and eliminating the need for tedious medical exams or blood tests. Their primary target audience includes young families, new homeowners, and modern parents across Canada who desperately need straightforward financial protection without the hassle of a weeks-long paper process. What sets PolicyMe apart in the archaic financial services sector is its radical transparency, its user-centric UX that reduces the application to just 20 minutes, and its highly efficient operating model that passes operational savings directly to the consumer—often resulting in rates significantly cheaper than traditional legacy providers.
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