Coaching & Outreach Specialist

Chegg Inc. • Remote (CA), CA

3d • $57,350 - $90,650 • Remote

About The Position

This is a Full-time role. Candidates Must have consistent availability for evening hours (5–9 PM ET / 2–6 PM PT). As a Skills Outreach Coordinator, you will play a hands-on role in providing coaching support and deepening our understanding of student outcomes. Approximately half of your time will be dedicated to delivering professional development coaching — supporting students in applying their learning to real career goals, working within established frameworks, through participating in live and asynchronous coaching sessions. The other half will focus on structured student outreach designed to gather meaningful data on student confidence, skills application, and the barriers they face throughout the program. This role blends coaching and structured student listening, with performance anchored in student engagement, data quality, and completeness. Your insights will directly inform how the coaching team evolves its support and resources. You will work closely with your manager and peers, operating within established processes while contributing to a student-first culture.

Requirements

• Bachelor's degree or equivalent experience
• Strong interpersonal and communication skills with the ability to engage and motivate students through digital platforms
• Experience with professional development coaching and career coaching (ICF Certified is a plus!)
• Ability to apply established coaching frameworks and incorporate feedback from manager and peers
• Comfortable conducting structured conversations and translating student input into clear, organized data
• Highly organized with experience tracking and documenting communications in CRM tools
• Proven ability to manage multiple priorities and work independently toward defined goals
• Empathetic, student-first approach with a passion for helping others succeed
• Proficient in Microsoft Office, Teams, and CRM tools
• Must have consistent availability for evening hours (5–9 PM ET / 2–6 PM PT)

Nice To Haves

• 2–3 years of experience in coaching, career development, outreach, learning & development, or a related field (preferably with adult learners)
• Experience with asynchronous messaging platforms is a plus (e.g. Zendesk, etc)

Responsibilities

• Deliver asynchronous coaching support to help students connect their learning to career advancement, using established coaching frameworks.
• Participate in and support live coaching sessions, co-facilitating or assisting as directed by the coaching team.
• Guide and motivate students toward their program and professional development goals.
• Support students with diverse needs, backgrounds, and experiences using empathy and active listening.
• Collaborate with peers and manager to apply, refine, and stay consistent with coaching approaches.
• Document coaching interactions and student progress in CRM tools.
• Conduct structured outreach to students throughout and upon completion of the program to gather data on confidence levels, skills application, and perceived barriers to progress.
• Use discovery questions and active listening to surface meaningful, usable insights from student conversations.
• Log and submit outreach data in a complete, timely, and consistent format to support team analysis and program improvement.
• Identify patterns in student feedback and surface relevant observations to the coaching team.
• Support student engagement within the Community platform (The Hub).
• Maintain a student-first approach in every outreach interaction, demonstrating empathy and genuine interest in student success.

Benefits

• Competitive base salary and significant equity
• Healthcare, dental, and vision insurance are 100% covered for individual and meaningfully covered for families
• 401k plan options
• Flexible vacation
• Paid parental leave
• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level