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Two Chicks With A Side Hustle

Explore 18 remote customer service, support, and customer success openings for applicants in Canada. Employer postings and application options were checked November 2, 2026. Openings can close after this date. Province, language, experience, and travel requirements vary.


1. Avee Health — Customer Support Specialist (MOA)

Location: Remote — anywhere in Canada

Support patients with appointments and service questions by phone, email, and chat. Full-time.

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2. PolicyMe — Customer Success Specialist

Location: Remote — Ontario

Support insurance customers and policy servicing. Relevant customer service or insurance experience required.

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3. Flex — Customer Experience Specialist

Location: Remote — Canada

Contract role supporting banking, credit, and payments customers. Financial services support experience requested.

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4. Sezzle — Customer Service Agent — English/French

Location: Remote — Canada

Assist customers through email, live chat, and phone. Bilingual English/French role.

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5. Affirm — Product Support Specialist I (Merchant Care)

Location: Remote — Canada

Support merchant partners with technical and operational issues. English and French fluency required.

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6. Cardata — Customer Success Associate

Location: Remote — Canada

Prepare reports, analyze customer program data, and support customer success managers. Strong Excel skills requested.

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7. Cardata — Manager, Customer Support

Location: Remote — Canada

Customer support leadership role for candidates with relevant support and management experience.

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8. Roofr — Customer Support Specialist — Bilingual English/Spanish

Location: Remote — Canada

Assist software customers through live phone and chat interactions in English and Spanish.

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9. Roofr — Customer Success Manager

Location: Remote — Canada

Manage customer relationships, product adoption, and account success.

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10. Roofr — Onboarding Manager — Bilingual Spanish

Location: Remote — Canada

Help customers onboard to the platform. Bilingual Spanish role.

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11. Axon — Sr Technical Support Representative

Location: Remote — Canada

Troubleshoot customer hardware, software, and networking issues. Technical experience and eligibility for RCMP clearance required.

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12. Sutherland — Customer Service Representative — Temporary

Location: Work from home — Canadian posting

Full-time temporary role supporting scholarship program inquiries. Assignment is listed through April 3, 2027. Confirm eligible province during application.

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13. Foundever — Bilingual Customer Service Representative

Location: Remote — listed for New Brunswick, Canada

Support automotive customers in English and French. At least six months of customer service experience requested.

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14. Tailscale — Customer Reliability Engineer

Location: Remote — Canada

Technical customer support role for a networking and secure connectivity platform.

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15. SOCi — Customer Success Manager

Location: Remote — Vancouver, Canada listing

Manage customer relationships, adoption, retention, and growth for a marketing software platform.

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16. PointClickCare — Sr. Customer Success Manager

Location: Remote — Canada; client travel required

Senior healthcare software customer success role. Relevant customer-facing SaaS and healthcare account experience requested.

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17. PointClickCare — Canada — Sr. Solutions Analyst (TAM–Clinical)

Location: Remote — Canada; required office-event travel

Resolve complex healthcare software queries and technical issues. Experience with clinical workflows is relevant.

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18. BlueCat — Manager, Customer Success Management

Location: Remote — Canada

Lead a pooled customer success team and oversee customer adoption, retention, and service delivery.

Apply Here