About the Role 

What you will work on

Customer Experience & Communication

• Work with a team of customer support specialists to provide timely, thoughtful responses to guardians’ and students’ questions and concerns
• Serve as the primary day-to-day point of contact for assigned customer accounts post-sale
• Facilitate clear, consistent communication between mentors and guardians/students to monitor match fit, engagement, and overall satisfaction
• Engage directly with families to understand students’ academic needs, extracurricular commitments, and evolving goals

Retention, Re-engagement & Loyalty

• Monitor consistency of scheduled mentor sessions and identify opportunities to increase engagement, retention, and session frequency
• Identify, segment, and prioritize re-engagement opportunities using customer data, engagement history, and behavioral patterns
• Conduct personalized outreach via email, text, and phone to re-engage paused, seasonal, and at-risk customers and build systems for every manual outreach to scale this

Transitions, Renewals & Upsell

• Gather insights on seasonal changes, academic transitions, and family needs to provide additional value and tailored solutions
• Ensure smooth transitions for guardians and students experiencing mentor changes by closing rematch deals
• Make thoughtful mentor recommendations based on student needs, learning styles, and mentor availability
• Lead renewal & upsell conversations and ensure customers are successfully retained and locked in for the school year

Systems, Data & Operational Efficiency

• Work through comprehensive customer spreadsheets and internal tools to track engagement, identify trends, and inform outreach strategy
• Use data analysis to identify seasonal upsell opportunities, service gaps, and additional customer needs
• Proactively communicate product updates and policy changes to relevant stakeholders and customers
• Collaborate cross-functionally with Sales, Marketing, Engineering, Product, and Mentor Management to share customer insights and improve experiences
• Drive improvements in tooling, workflows, and process documentation to increase efficiency and scale customer operations
• Contribute to playbooks, process improvements, and strategic planning initiatives across the customer experience organization

Strategic Support & Cross-Functional Collaboration

• Partner with leadership to develop customer segmentation strategies and engagement frameworks
• Support cross-functional coordination between sales, operations, and mentor management teams
• Participate in accountability sessions, planning meetings, and retrospectives
• Provide customer insights and feedback to inform broader business and product decisions

Skills & Experience

• Experience using AI tools to build workflows, agents, or automated customer support systems
• Strong analytical skills; experience using SQL and spreadsheets to segment customer data and scale outreach
• Proficiency with CRMs (e.g., HubSpot) to build workflows, lists, and automated, personalized outreach
• Highly organized with strong documentation practices to support scalable, individualized customer engagement
• At least 2 years of experience in an operations, customer success, or account management role
• Deep understanding of the needs and psychology of students and parents navigating K–12 education and the college process
• Excellent verbal and written communication skills with the ability to represent the brand effectively across diverse audiences
• Metrics-driven mindset with the ability to analyze data, identify trends, and turn insights into action
• Systems thinker with a passion for improving onboarding, retention, and lifetime value through better processes and tooling
• Comfortable managing multiple priorities, meeting deadlines, and iterating quickly in a fast-paced environment
• Entrepreneurial, tech-minded, and motivated to continuously improve operational efficiency
• Passionate about reimagining the future of K–12 education