Sign upLog in

Supervisor, Enrollment

Chegg, Inc.

Carson City, Nevada

Apply
JOB DETAILS
SKILLS
Best Practices, Coaching, Communication Skills, Continuous Improvement, Cross-Functional, Customer Relationship Management (CRM) Systems, Establish Priorities, Leadership, Mentoring, Metrics, Onboarding, Operational Strategy, Operations Processes, Organizational Skills, Pattern Analysis, Performance Reviews, Presentation/Verbal Skills, Process Improvement, Product Engineering, Quality Management, Reporting Dashboards, Sales, Short Messaging Service (SMS), Team Lead/Manager, User Documentation, Writing Skills
LOCATION
Carson City, Nevada
POSTED
6 days ago
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 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 behavior

About the Company

C

Chegg, Inc.