--- title: 'Customer Success Specialist (Remote) at PolicyMe' canonical: 'https://feeny.ai/job/customer-success-specialist-remote-policyme-ontario-6jnrw8nkh5at' type: 'job' last_seen: '2026-09-07' --- # Customer Success Specialist (Remote) at PolicyMe - **Company:** PolicyMe - **Location:** Ontario, Canada - **Employment:** full-time - **Work type:** remote - **Posted:** 2026-09-01 - **Last confirmed live:** 2026-09-07 - **Apply:** https://jobs.lever.co/policyme/d5f14a0e-b004-41f4-9a48-eca276b40cee ## Job description 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 ## Company Overview - **One-liner**: PolicyMe is a Canadian digital insurance platform that makes life, health, and home & auto coverage simple, affordable, and honest by combining smart technology with licensed advisors. - **Entity Type**: Private (venture-backed, $43.7M total funding) - **Headquarters**: Toronto, Ontario, Canada - **Founded**: 2018 - **Founders**: Andrew Ostro (CEO), Laura McKay (COO), Jeff McKay (CTO) ## Core Business - **Primary industry/industries**: Insurance (Life, Critical Illness, Health & Dental, Home & Auto) - **Target customers**: B2C – individual Canadians seeking personal insurance coverage - **Mission or purpose statement**: "Ensuring every Canadian has access to fair and comprehensive coverage, backed by smart technology and people who care." ## Products & Services - **[Life Insurance]**: Direct-to-consumer term life insurance, fully online, with guaranteed coverage options. Issued by Securian Canada. - **[Critical Illness Insurance]**: A tax-free lump-sum payout upon diagnosis of a covered condition. PolicyMe covers more conditions than any other Canadian provider. - **[Health & Dental Insurance]**: Coverage for prescriptions, dental care, vision, and paramedical services. Individual and family plans available. - **[Home & Auto Insurance]**: Brokerage service – compares partner insurers to find the best price for home and car coverage (currently available only in Ontario). - **[White-Label Platform]**: Powers insurance products behind some of Canada’s largest insurance brands – their technology and products under a partner’s name. ## Market Standing - **Valuation/Market Cap**: Not disclosed - **Key Metrics**: - Annual Revenue: $19.5M (LinkedIn estimate) - Total Funding: $43.7M across 8 rounds - Coverage issued: $15B+ in coverage - Customers: 50,000+ families covered - **Notable Investors/Partners**: Not explicitly listed in available sources; backed by venture capital (details not public). Insurance partner: Securian Canada (Canadian Premier Life Insurance Company). - **Growth Signals**: - Headcount: 100 employees (+28.7% YoY) - Named to Globe & Mail’s Top Growing Companies list (2025) - Deloitte’s Technology Fast 500 (2025) - A+ rating from Better Business Bureau - Expanding product lines and geographic coverage ## Competitive Advantages - **Direct-to-consumer model** for life, critical illness, and health & dental – eliminates middlemen and overhead, lowering premiums. - **Technology-driven but human-backed** – online application in ~20 minutes with optional support from licensed advisors (no chatbots, no call centres). - **Broader coverage** – critical illness policy covers more conditions than any other Canadian insurer. - **White-label platform** strength – underlying technology powers products for major Canadian insurance brands, demonstrating trust and scalability. - **Remote-first culture** with no in-office mandate, attracting top talent across Canada. ## Strategic Focus - Continue to grow the direct-to-consumer insurance business across all Canadian provinces and territories. - Scale the home & auto brokerage to more regions (currently Ontario-only for those products). - Deepen partnerships with large insurance brands via the white-label platform. - Invest in technology and automation to further simplify the customer experience and reduce costs. ## Why Work Here - **Remote-first**: No in-office mandate; work from anywhere in Canada with the option to use a downtown Toronto office. - **Compensation & Benefits**: Competitive total compensation reviewed annually; comprehensive benefits from day 1; 4 weeks paid time off. - **Professional Development**: Learning resources, unique growth opportunities, and support for continuous skill-building. - **Culture**: Emphasis on trust, open dialogue, and continuous feedback. Regular in-person and virtual team events (e.g., summer island party, holiday celebrations). - **Engineering Culture**: Modern tech stack (details not public), focus on building large-scale distributed systems; leadership includes CTO with Bloomberg background. - **Open Roles**: Software Engineer (Junior, Senior, Manager), Principal Product Manager, Licensed Insurance Advisors, Talent Acquisition Manager – all remote. ## Sources 1. [PolicyMe Careers Page](https://www.policyme.com/careers) 2. [PolicyMe About Us](https://www.policyme.com/about-us) 3. [PolicyMe Main Site](https://www.policyme.com/) 4. [PolicyMe LinkedIn Company Page](https://linkedin.com/company/policymeinsurance) 5. [PolicyMe Job Postings on Lever](https://jobs.lever.co/policyme) ## Other roles at PolicyMe - [Talent Acquisition Partner](https://feeny.ai/job/talent-acquisition-partner-policyme-toronto-1y268852y63x) — Toronto, Canada - [Junior Software Engineer (Remote)](https://feeny.ai/job/junior-software-engineer-remote-policyme-ontario-8akdx2tg7yhg) — Ontario, Canada - [Senior Software Engineer (Remote)](https://feeny.ai/job/senior-software-engineer-remote-policyme-ontario-61wjhacyf0ns) — Ontario, Canada - [Software Engineer Manager (Remote)](https://feeny.ai/job/software-engineer-manager-remote-policyme-ontario-gxvma1t6r5rz) — Ontario, Canada - [Principal Product Manager, Accounts & Automation (Remote)](https://feeny.ai/job/principal-product-manager-accounts-automation-remote-policyme-toronto-s0jrdc1h9kbz) — Toronto, Canada - [Software Engineer (Remote)](https://feeny.ai/job/software-engineer-remote-policyme-ontario-vdpxqct709qq) — Ontario, Canada - [Bilingual Licensed Insurance Advisor (Remote)](https://feeny.ai/job/bilingual-licensed-insurance-advisor-remote-policyme-toronto-y6n7amgjc5me) — Toronto, Canada - [Bilingual Quebec Licensed Insurance Advisor (Remote)](https://feeny.ai/job/bilingual-quebec-licensed-insurance-advisor-remote-policyme-in-j9djcw1ym12p) — IN, Canada - [Join PolicyMe’s Talent Network for future opportunities!](https://feeny.ai/job/join-policyme-s-talent-network-for-future-opportunities-policyme-remote-qtek7ezebbhq)