About this role.
PolicyMe is hiring a Customer Success Specialist to guide life-insurance applicants and policyholders through underwriting, servicing, billing, and policy-change processes. The role manages an active caseload, coordinates medical exams and underwriting requirements, and handles inbound calls and client email communication. Success requires precise recordkeeping, empathy, comfort with HubSpot and Front, and cross-functional collaboration with Advisors, QA, Sales, and Customer Service. This is a remote-first Canadian role with core Eastern Time hours and possible support for Pacific Time coverage.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
3/5Pace & Pressure
4/5Autonomy Level
3/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
Skills and capabilities most closely associated with this opportunity.
Sample interview questions
I would prioritize cases by underwriting deadlines, client impact, and outstanding requirements, then maintain a daily task queue in the CRM. I would document every action clearly, set follow-up reminders, and escalate exceptions early so that applications continue moving forward.
I would acknowledge the frustration, explain the next step in plain language without making promises I cannot keep, and confirm what I will do to help. I would coordinate with the vendor, provide the customer with a clear update timeline, and follow through until the issue is resolved or appropriately escalated.
I would verify the requestor’s identity and review the required documentation and policy details before making changes. After processing, I would confirm the update in the appropriate system, record the action thoroughly, and communicate completion or any missing requirements to the client.
I start by understanding each tool’s role in the workflow, practicing common tasks, and creating concise reference notes for repeat processes. I also use queues, templates, tags, and reminders consistently so that communication and follow-ups remain organized across systems.
In a previous role, I was advised to make my follow-up messages more explicit about timing and next steps. I adopted a clearer structure that summarized the issue, ownership, and expected update date, which reduced repeat inquiries and improved customer confidence.
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.
Compensation
Additional Information
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 www.policyme.com.
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.
Annual salary information is not provided for this position. Explore salary ranges for similar roles in our Salary Directory ›
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