Posted May 2, 2026

Supervisor, Success Coaching (Video)

Job Description

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, live video coaching and team leadership role. In this position, you will guide and support a small team of Student Success Coaches while maintaining an individual coaching 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 live, interactive environments, have strong leadership instincts, and are energized by both student-facing impact and guiding a high-performing coaching 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 understand and follow best practices.

Ensure team adherence to high standards of coaching quality, reflective practice, and accountability for learner outcomes.

Lead operational execution for the team, including coordinating workflows, session scheduling, template management, process updates, and running regular team meetings to ensure alignment and focus on learner success.

Support day-to-day cross-functional collaboration by sharing coaching feedback and participating in routine coordination with Enrollment, Enablement, Outcomes, and related teams.

Student-Facing Coaching

Maintain a flexible student caseload, delivering high-touch, reflective coaching across all learner types.

Use learner data and progress insights to guide coaching and follow-up conversations.

Foster skill-building, goal setting, and learner ownership through thoughtful, personalized support.

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 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 live video coaching, with a focus on student outcomes and engagement.

1+ years of leadership experience, including mentoring, guiding peers, and managing performance. (preferred)

Excellent verbal and written communication skills, with the ability to build trust and inspire action.

Demonstrated ability to balance individual coaching responsibilities with team supervision and operational execution.

Ability to leverage data and insights to guide coaching decisions and team prioritization.

Strong problem-solving, decision-making, and escalation skills.

Understanding of adult learning principles (andragogy); teaching or counseling experience is a plus.

Strong organizational skills and the ability to manage competing priorities in a dynamic environment.

Experience with CRM and communication tools (Planhat, Zendesk, Zoom) is a plus.

Availability to work Pacific Time business hours (9 a.m. – 5 p.m. PST) is preferred.

The target base salary for the requisition is $87,000 and the Pay Transparency Ranges are:

The base salary pay range for this position is $69,600 to $104,300. Although this range represents the full range for the position, the actual pay will vary within this range based on geographic location, job type, professional experience, and other factors.

In addition, Chegg offers a comprehensive benefits plan for eligible employees, including medical, dental, vision, life and supplemental life insurance, short-and long-term disability, mental health support, parental leave, paid time off, paid holidays, 401(k) with matching contributions, Flexible Spending Account (FSA) and Health Savings Account (H.S.A.) options, an Employee Stock Purchase Plan, and other benefits found at: https://www.chegg.com/about/working-at-chegg/benefits/.

Why do we exist?

Students are working harder than ever before to stabilize their future. Our recent research study called State of the Student shows that nearly 3 out of 4 students are working to support themselves through college and 1 in 3 students feel pressure to spend more than they can afford. We founded our business on provided affordable textbook rental options to address these issues. Since then, we’ve expanded our offerings to supplement many facets of higher educational learning through Chegg Study, Chegg Math, Chegg Writing, Chegg Internships, Chegg Skills, and more to support students beyond their college experience. These offerings lower financial concerns for students by modernizing their learning experience. We exist so students everywhere have a smarter, faster, more affordable way to student.