Customer Education & Enablement Specialist

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Customer Education & Enablement Specialist based in Canada. This part-time role is focused on helping B2B customers move smoothly from implementation to meaningful, sustained product adoption. You’ll lead onboarding, facilitate engaging virtual training, and create educational resources for diverse audiences across institutional and enterprise partners. The role sits at the intersection of customer success, education, operations, content, and technology. You’ll simplify complex product concepts and build programs that help customers reach value quickly and confidently. You’ll also use data and AI-assisted workflows to improve training effectiveness and streamline customer operations. The ideal environment is fast-moving, customer-focused, and well suited to someone who takes ownership and continuously looks for better ways to work. Accountabilities Lead customer onboarding and implementation sessions, ensuring customers are fully prepared before transitioning accounts to Customer Success Managers.Deliver live virtual training for faculty, students, coaches, HR professionals, and other customer audiences, adapting content to different needs and levels of expertise.Run recurring office hours and other educational sessions to reinforce product knowledge and encourage adoption.Create, maintain, and organize customer-facing educational resources, including product guides, faculty materials, student assignments, knowledge-base content, FAQs, newsletters, and video resources.Develop and execute adoption initiatives such as Train-the-Trainer programs, certifications, semester launch kits, email sequences, and targeted adoption campaigns.Coordinate onboarding-phase customer marketing activities and provide clear briefs to Marketing teams responsible for producing campaign assets.Maintain onboarding-related CRM records, meeting summaries, training schedules, AI-generated meeting notes, follow-up communications, and resource distribution.Track webinar attendance, product adoption, and educational resource usage, using these insights to communicate training effectiveness to the Customer Success team.Operate and monitor AI-assisted workflows established by Customer Success leadership, making minor adjustments where appropriate and escalating issues requiring broader redesign.Continuously identify opportunities to improve onboarding, education, customer engagement, and operational efficiency as products and customer needs evolve. Requirements 1–3 years of experience in customer education, customer training, instructional design, enablement, or customer operations.Demonstrated ability to facilitate live virtual training for diverse audiences, including educators, students, HR professionals, coaches, or institutional stakeholders.Strong written communication skills, with the ability to independently create clear guides, newsletters, documentation, and educational materials.Working knowledge of CRM systems and strong organizational skills, with excellent follow-through and the ability to consistently close operational loops.Comfortable adopting AI tools and new technologies quickly, with curiosity about how AI can improve customer education and business workflows.Based in Canada, with authorization to work in Canada and availability to collaborate across Pacific, Mountain, and Eastern time zones.HubSpot experience as an administrator or power user is highly desirable.Experience in higher education, career services, workforce development, or related fields is an advantage.Hands-on experience using AI assistants such as Claude, Fireflies, or comparable workplace tools is a plus.Experience with webinar or learning-management platforms, along with basic video production or editing skills, is beneficial.Experience developing Train-the-Trainer programs or certification initiatives is an additional advantage.A proactive, a