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Chegg Inc. Supervisor, Enrollment in Olympia, Washington

Job Description

Role Overview

At Chegg Skills, we focus on delivering an exceptional return on a learner's time and investment. Part of our Student Success team, our lead-to-verification roles guide learners from initial interest and enrollment through orientation and full verification, using structured processes and personalized outreach.

We are seeking a Supervisor, Enrollment to lead a small team of Outreach Coordinators while also working directly with learners to support them through the enrollment process. You will guide your team in delivering high-quality, data-informed outreach that converts leads into enrolled learners, while also ensuring learners understand program requirements, benefits, and next steps.

This role balances direct learner engagement with team leadership, process ownership, and cross-functional collaboration, making it ideal for those energized by both operational execution and strategic impact.

Responsibilities

Team Leadership & Supervision

  • Manage, mentor, and support a small team of Outreach Coordinators, providing feedback, performance guidance, and development support.

  • Serve as the role expert for enrollment, ensuring team members follow processes and best practices.

  • Monitor team metrics and outcomes, coaching team members to improve enrollment conversion and engagement.

  • Conduct regular check-ins, 1:1s, and performance reviews to maintain alignment and accountability.

  • Provide coverage for team members during absences and support additional workflow needs.

  • Lead team-level operational workflows, including outreach prioritization, reporting, process adherence, and running team meetings to maintain alignment.

Enrollment Management & Learner Outreach

  • Own outreach and conversion for the Lead ? Enroll phase and maintain a flexible learner caseload for the following enrollment phases through proactive outreach via email, SMS, and phone calls:

  • Enroll ? Verification

  • Eligible for Re-enrollment

  • Nurture leads by clarifying program prerequisites, benefits, employer cover

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