Adult Learning, Coaching, Communication Skills, Customer Relationship Management (CRM) Systems, Organizational Skills, Presentation/Verbal Skills, Set Goals, Training/Teaching, Writing Skills, ZenDesk
LOCATION
Annapolis, Maryland
POSTED
Today
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 Student Success Coach to join our dynamic team. In this high-touch, video coaching role, you will guide, motivate, and provide personalized support for a diverse group of learners through live video sessions, helping them build strong habits, set meaningful goals, and overcome obstacles. Your work will center on reflective coaching that drives accountability, fosters growth, and empowers learners to take ownership of their learning journeys. Success in this role is measured by your students' progress, retention, and graduation rates.
This role is ideal for coaches who thrive in live, interactive sessions, can sustain energy across multiple personalized interactions per week, and are committed to driving meaningful growth for each learner.
Responsibilities
Guide, motivate, and coach learners with diverse needs, backgrounds, and experiences through relationship-based, live video coaching.
Deliver high-touch, live video coaching sessions (20-30 minutes each) with up to 40-50 sessions per week, ensuring each interaction is personalized to the learner's goals, challenges, and circumstances.
Prepare sessions by reviewing learner history, progress, and behavioral data to guide reflective, targeted coaching conversations.
Document coaching interactions and learner progress in CRM systems to maintain continuity and inform future sessions.
Conduct follow-up communications to reinforce insights, clarify next steps, and sustain accountability between sessions.
Drive accountability, motivation, and skill-building through thoughtful questioning, reflection, and goal-setting, helping learners overcome obstacles and take ownership of their learning journey.
Collaborate with Enrollment Managers, Outreach Coordinators, and the enablement team to address learner needs and ensure a smooth, supportive learner experience.
Participate in virtual workshops, group coaching sessions, and office hours as needed to reinforce learning and engagement.
Provide feedback on coaching processes, tools, and strategies to optimize learner outcomes.
Partner with the Enablement team to test and refine coaching strategies and contribute to the ongoing development of the coaching toolkit.
Qualifications:
3-5+ years of experience in coaching, student success, or related learner-facing roles.
Strong passion for live, interactive coaching, with the ability to engage learners across multiple sessions per week.
Comfort managing a high-volume coaching schedule, while delivering quality, individualized support.
Ability to guide learners toward self-discovery and ownership, empowering them to set goals, build habits, and overcome challenges.
Excellent verbal and written communication skills, with strong empathy and clarity.
Demonstrated ability to motivate learners, including reconnecting them to their goals and "why."
Understanding of adult learning principles (andragogy); teaching or counseling experience is a plus.
Ability to manage competing priorities in a fast-paced, evolving environment.
Strong work ethic and commitment to learner outcomes.
Availability 9 am-5 pm PST
Experience with Planhat, Zendesk, or similar CRM and support tools is a plus.
The base salary pay range for this position is between USD 64800 to USD 85000. 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/. Benefits - Chegg Resources you need to succeed. We believe