Supervisor, Success Coaching

Job Description

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. 

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. 

• 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. 

• Excellent written and verbal 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. 

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.

Life at Chegg: http://youtu.be/Fwf90zgaOLA

Chegg Corporate Career Page: https://jobs.chegg.com/

Chegg India: http://www.cheggindia.com/

Chegg Israel: http://www.chegg.com/about/working-at-chegg/israel/

Chegg Skills:  https://www.chegg.com/skills

 
Chegg out our culture and benefits!

http://www.chegg.com/about/working-at-chegg/benefits/

Chegg is an equal opportunity employer