About the Role

We are looking for an ambitious Family Success Specialist with a focus on Customer Support & Success, who is excited to join a small but mighty team that is revolutionizing the way students learn and pursue their passions.

This role will be responsible for driving customer satisfaction and loyalty by optimizing the student and parent experience. The ideal candidate will be able to be both hands-on and strategic. The Ops Manager is responsible for supporting customer inquiries as they arrive while building playbooks and standardizing processes in order to improve operational efficiency and experiences across the customer lifecycle.

If you are a curious, systems-minded operator with a strong work ethic and excellent communication skills, let’s talk! If you are passionate about education and are excited to join an early-stage startup with ambitious goals, hesitate no more!

What you will work on

You’ll drive customer satisfaction and loyalty throughout our student journeys by ensuring that every student receives the skills, confidence, and mentorship they need to reach their goals and achieve success. You’ll accomplish this by reducing friction wherever possible so students can focus on having a positive learning experience. This includes guiding the student and parent through onboarding, mentor matching, lesson scheduling, and learning plan development. Throughout the customer journey, you will be responsible for providing an exemplary experience, as measured by customer satisfaction, pair health, and student/mentor engagement metrics.

Core responsibilities include:

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