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JOB REQUIREMENTS: Role Overview At Chegg Skills, we\'re on a mission to deliver an unprecedented return on students\' time and money. Our programs deliver exceptional outcomes at market-leading prices by providing a seamless experience from enrollment through graduation. We are looking for a Supervisor, Success Coaching, to join our team in a high-touch, asynchronous coaching and team leadership role. In this position, you will guide and support a small team of Student Success Coaches while maintaining a flexible learner caseload. You will ensure high-quality, reflective coaching across all learner types, drive accountability for learner outcomes, and support your team in delivering consistent, personalized guidance. This role is ideal for individuals who thrive in written, interactive environments, have strong leadership instincts, and are energized by both student-facing impact and guiding a high-performing coaching team. You will serve as the role expert for your team, providing guidance on processes, answering questions, and supporting best practices to ensure high-quality coaching across the team. Responsibilities Team Leadership & Supervision * Manage, mentor, and support a small team of Student Success Coaches, providing feedback, performance guidance, and development plans. * Serve as the role expert for your team, answering questions, clarifying processes, and ensuring coaches follow best practices. * Monitor team metrics and outcomes, identify coaching gaps, and guide team members in adjusting approaches to improve learner success. * Lead team-level operational workflows, including outreach prioritization, reporting, process adherence, and running team meetings to maintain alignment. * Provide direct coverage during team OOOs and support additional operational needs as required. * Conduct weekly dash reviews, 1:1 meetings, and team check-ins to maintain alignment and operational excellence. * Support day-to-day cross-functional collaboration by sharing coaching feedback and participating in routine coordination with Success Team Leadership, Enablement, Outcomes, and related teams. Student-Facing Coaching (Asynchronous) * Maintain a flexible learner caseload, delivering high-touch, reflective coaching primarily via SMS and email, approximately 100 learner interactions per week. * Deliver prepared, intentional coaching interactions informed by learner progress, behavioral data, and prior engagement. * Reinforce outcomes and accountability through clear follow-up and continuity between coaching touchpoints. * Drive skill-building, goal setting, and learner ownership through thoughtful questioning, reflection, and personalized support. * Provide live video coaching sessions as needed to address learner needs, though infrequently. Continuous Improvement * Identify opportunities to improve workflows, outreach strategies, and operational processes. * Lead or contribute to team-level projects that enhance outcomes and learner experience. * Develop and share best practices for learner engagement across the team. * Partner with Enablement and Outcomes teams to test and refine coaching strategies and contribute to the ongoing development of coaching resources and best practices. * Provide feedback on team processes, tools, and engagement strategies to optimize learner outcomes and operational efficiency. Qualifications * 4+ years of experience in student success, coaching, or related learner-facing roles in a high-growth, fast-paced environment. * Proven experience in high-volume asynchronous coaching, with a focus on student outcomes and engagement. * 1+ years of strong leadership experience, including mentoring, guiding peers, and managing performance. To view the full job description please use the link below. https://www.aplitrak.com/?adid=YmJnZW5lcmljLjgwMTA1Ljg3NzBAY2hlZ2djb21wLmFwbGl0cmFrLmNvbQ ***** APPLICATION INSTRUCTIONS: Apply Online: https://www.aplitrak.com/?adid=YmJnZW5lcmljLjgwMTA1Ljg3NzBAY2hlZ2djb21wLmFwbGl0cmFrLmNvbQ