Job Information
Chegg Inc. Supervisor, Success Coaching in Olympia, Washington
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.
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