Supervisor, Enrollment Full Time

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 coverage, and enrollment requirements.
• Maintain strong program knowledge, including eligibility requirements, common learner questions, and common enrollment friction points.
• Support learners in completing enrollment agreements, verification, and other required onboarding steps.
• Address learner questions and identify when issues require triage to specialized internal teams.
• Use behavioral data, engagement signals, and feedback to shape outreach timing, messaging, and follow-up strategy.
• Apply discovery questions and active listening to understand learner motivation, barriers, and readiness.
• Document interactions and progress in CRM tools for visibility across the learner lifecycle.
• Partner with cross-functional teams to ensure a coordinated learner experience across the enrollment journey.

Continuous Improvement & Strategic Contribution

• Identify opportunities to improve workflows, outreach strategies, and operational processes.
• Lead or contribute to team-level projects that enhance enrollment conversion and learner experience.
• Develop and share best practices for learner engagement across the team.
• Analyze engagement patterns and performance data to guide process improvements.
• Provide feedback to leadership and cross-functional teams on tools, systems, and processes affecting enrollment.
• Collaborate with Product and Engineering teams to identify and flag time-sensitive technical issues affecting enrollment workflows (e.g., learner-facing dashboard issues or internal system errors).
• Escalate issues requiring employer or partner intervention as needed to ensure timely resolution.

Qualifications

• 4+ years in enrollment, learner engagement, customer success, sales, or related roles in fast-paced environments.
• 1+ years of experience managing or mentoring team members and supporting performance development. (preferred)
• Proven ability to manage a high volume of learner interactions while maintaining quality and accuracy.
• Excellent written and verbal communication skills, with the ability to motivate action and build trust.
• Experience using behavioral data or performance metrics to guide outreach strategy.
• Ability to balance direct learner engagement with team leadership and operational responsibilities.
• Strong problem-solving, decision-making, and escalation skills.
• Excellent organization and time management in a high-volume environment.
• Experience with CRM systems (Planhat, Salesforce, Zendesk, or similar) is a plus.
• Familiarity with adult learners, workforce education programs, or employer-sponsored benefits 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.

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Chegg out our culture and benefits!

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Chegg is an equal opportunity employer