Manager, Student Success

Manager, Student Success

US Remote

The Role 

• At Chegg, we’re on a mission to deliver an unprecedented return on a student’s time and money. Our programs deliver exceptional outcomes at market-leading prices by offering seamless experiences for students from the day they enroll at Chegg Skills until the day they graduate. 

• As a Manager of Student Success, you will lead a team of asynchronous and synchronous Success Coaches, focusing on balancing personalization, efficiency, and measurable results. You will instill a sales mindset in the coaches, empowering them to continually "sell" the student on their own potential and capabilities. This role emphasizes achieving and exceeding conversion goals early in the program, sustaining progress throughout, and driving graduation outcomes to meet revenue targets. You’ll ensure the team consistently delivers high performance aligned with business goals, navigating the monthly sales cycle while effectively managing long-term cohorts. 

Responsibilities 

• Hire, train, manage, and develop a team of asynchronous and synchronous Success Coaches in a remote, high-tech, and high-touch environment. 

• Achieve and exceed revenue and success metrics by ensuring students convert early in the program and progress toward graduation. 

• Focus on early conversion goals by ensuring students build strong habits and engage deeply with the program from the start. 

• Design and implement strategic remediation techniques to support students at risk of falling behind, ensuring proactive interventions that improve retention and outcomes. 

• Drive graduation outcomes by maintaining engagement, motivation, and momentum for students through the end of the program, ensuring both individual and team performance aligns with organizational revenue goals. 

• Build a team culture of accountability, feedback, and experimentation, ensuring every team member is contributing to measurable results. 

• Encourage the use of diverse outreach modalities (email, text, video) and tactics (1:1, 1:many) to optimize student outcomes. Document and refine best practices into clear playbooks that scale effectively. 

• Collaborate with Business Operations, Product, and other teams to systematize workflows in business applications (e.g., Salesforce), streamlining processes that enable your team to achieve targets. 

• Work cross-functionally with other coaching departments (e.g., Careers, Instructors, Mentors) to break down silos and more efficiently drive student and business success. 

• Define workflows and triggers that initiate proactive and reactive outreach by Success Coaches to at-risk students, ensuring swift and effective support. 

• Set and manage clear performance metrics for individual team members that align with broader Chegg Skills revenue and success goals. Ensure the team consistently hits or exceeds targets. 

• Regularly collect and surface quantitative data and student feedback to identify areas for improvement in processes, curriculum, and support systems. 

• Navigate the monthly sales cycle with urgency and precision, ensuring near-term targets are met while maintaining a strategic focus on long-term cohort management and success. 

Requirements 

• 1+ year of experience as a people manager. 

• Experience in student or customer-facing roles. 

• Strong verbal and written communication skills. 

• Proven success in setting goals and achieving or exceeding revenue and performance targets, particularly in fast-paced environments. 

• Demonstrated ability to provide actionable feedback, manage performance, and coach team members to success. 

• Experience de-escalating challenging situations and navigating complex problem-solving scenarios. 

• Ability to balance short-term revenue goals with long-term strategy, making data-informed decisions in dynamic circumstances. 

Preferred Qualifications 

• Formal coaching certification or experience. 

• Experience leading a sales or account management function with measurable revenue outcomes. 

• Experience managing teams through change and adapting to evolving business needs. 

• Proficiency in documenting processes, clarifying workflows, and optimizing cross-departmental collaboration. 

• Familiarity with journey mapping, workflow design, and other tools to support team efficiency.