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Customer Education & Enablement Specialist - Canada (Part-time)

πŸ“… Sep 4
Customer OnboardingCustomer EducationVirtual Training FacilitationInstructional Design
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πŸ“œ Description

  • Lead customer onboarding and implementation sessions, deliver virtual training, hold office hours, and confirm implementation before handoff to CSMs.
  • Create and maintain customer-facing guides, faculty resources, student assignments, knowledge base content, videos, and FAQs.
  • Build and run Train-the-Trainer certifications, launch kits, email sequences, and adoption campaigns.
  • Coordinate onboarding campaign timing and provide customer success briefs to Marketing.
  • Manage onboarding-phase HubSpot updates, meeting notes, schedules, follow-ups, and resource distribution.
  • Track training attendance, adoption, and resource usage; operate and monitor AI-assisted workflows defined by CS leadership.

πŸ› οΈ Requirements

  • 1–3 years in customer education, training, instructional design, or customer operations.
  • Experience facilitating live virtual training for diverse audiences.
  • Strong written communication skills, including producing guides, newsletters, and documentation.
  • Working knowledge of CRM tools, strong organization, and reliable follow-through.
  • Curiosity about AI tools and ability to adopt new technology quickly.
  • Based in Canada with work authorization and availability across Pacific, Mountain, or Eastern time zones.
  • Preferred: HubSpot experience; higher education, career services, or workforce development experience; AI assistant, webinar/LMS, video editing, or Train-the-Trainer experience.

✨ Benefits

  • Competitive salary
  • Fully remote work environment
  • Adoption Programs β€” build and run Train-the-Trainer certifications, semester launch kits, email sequences
  • 1–3 years in customer education, training, instructional design, or customer operations.
  • Comfortable facilitating live virtual training with diverse audiences (faculty, students, HR professionals).
  • Strong written communicator β€” can independently produce guides, newsletters, and documentation.
  • Curious about AI tools and quick to adopt new technology.
  • Based in Canada with work authorization; available on Pacific/Mountain/Eastern time zones.
Full job description
At Jobscan, we’re passionate about empowering job seekers to land more interviews with AI. We have helped millions of job seekers get more interviews in 100+ countries. Jobscan’s platform benefits job seekers, employers, universities, and communities. We're a fast-growing startup πŸš€. Since its founding in 2014, Jobscan has thrived for 11 years as a 100% self-funded company, achieving consistent profitability and rapid growth without VC investment. Recently, we’ve transformed into an AI-first company, leveraging cutting-edge tools to enhance operations and our product. This independence allows us to stay laser-focused on our customers, delivering impactful solutions for job seekers. Join us if you wish to be a part of a company that makes a real difference in people’s lives ❀️!

Summary

Jobscan is building a premium B2B business serving outcome-driven institutions that care deeply about employment results. This is not a script-following, high-volume support role.

As a Customer Enablement Specialist, you own the critical bridge between a signed contract and a thriving, fully engaged customer. You will lead onboarding, deliver live training, and curate educational resources across our university, outplacement, and enterprise partners.

This role is ideal for a proactive communicator and educator who excels at driving product adoption, simplifying complex concepts, and guiding partners toward long-term success.

At Jobscan, we’re passionate about empowering job seekers to land more interviews with AI. We have helped millions of job seekers get more interviews in 100+ countries. Jobscan’s platform benefits job seekers, employers, universities, and communities. We're a fast-growing startup πŸš€. Since its founding in 2014, Jobscan has thrived for 11 years as a 100% self-funded company, achieving consistent profitability and rapid growth without VC investment. Recently, we’ve transformed into an AI-first company, leveraging cutting-edge tools to enhance operations and our product. This independence allows us to stay laser-focused on our customers, delivering impactful solutions for job seekers. Join us if you wish to be a part of a company that makes a real difference in people’s lives ❀️! Benefits β€£ Competitive salary β€£ Fully remote work environment

What you'll be doing:

  • Customer Onboarding β€” lead standard onboarding and implementation sessions; deliver live virtual faculty, student, and coach training; run recurring office hours; confirm implementation is complete before handing accounts to the CSM.
  • Education & Content β€” own and maintain all customer-facing educational resources (Resume Builder, AI Optimizer, and LinkedIn guides; faculty guides and student assignments; Knowledge Base, video library, FAQs); keep content current as the product evolves.
  • Adoption Programs β€” build and run Train-the-Trainer certifications, semester launch kits, email sequences, and adoption campaigns that drive Time to First Value.
  • Customer Marketing Coordination β€” coordinate timing and launch of onboarding-phase campaigns and supply CS briefs to Marketing, which produces the assets (graphics, flyers, campaign production sit with the Marketing team).
  • Customer Operations β€” own onboarding-phase HubSpot updates, meeting summaries, Fireflies AI note management, training schedules, follow-up emails, and resource distribution. (CSMs continue logging their own relationship and renewal calls.)
  • Data & Reporting β€” track webinar attendance, adoption metrics, and resource utilization, and report training effectiveness to the CS team. (Dashboard design and build are owned by CS leadership.)
  • AI Workflows β€” implement and maintain AI-assisted workflows defined by CS leadership: day-to-day operation, monitoring, minor tweaks, and escalating anything that needs redesign. (Automation strategy, prioritization, and build are owned by the Director.)
  • What will help you succeed here:

  • 1–3 years in customer education, training, instructional design, or customer operations.
  • Comfortable facilitating live virtual training with diverse audiences (faculty, students, HR professionals).
  • Strong written communicator β€” can independently produce guides, newsletters, and documentation.
  • Working knowledge of CRM tools; highly organized with strong follow-through β€” closes loops.
  • Curious about AI tools and quick to adopt new technology.
  • Based in Canada with work authorization; available on Pacific/Mountain/Eastern time zones.
  • We’d love it if you also brought:

  • HubSpot experience specifically (admin or power user).
  • Experience in higher education, career services, or workforce development.
  • Hands-on use of AI assistants (Claude, Fireflies, or similar) in a work setting.
  • Webinar/LMS platform experience; basic video production or editing.
  • Train-the-Trainer or certification program experience.
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