Head of Customer Success

Head of Customer Success & Product

High-Growth EdTech Startup | Remote | Full-Time

Work Directly with the CEO & Founder | Potential Path to COO

🌱 About the Company

The company's mission is to unlock every student's potential. We believe every student deserves the opportunity to succeed, regardless of their past academic performance or circumstances.

The business has grown from approximately $400K to $3M in annual revenue in a remarkably short period, with the ambition of positively impacting millions of students.

🚀 The Opportunity

We're looking for an entrepreneurial, energetic, and resourceful leader who combines a founder's mindset with strong operational and people leadership skills.

Working directly with the CEO and Founder, you'll lead and scale Customer Success, Student Success, Product, and customer-facing systems, ensuring an outstanding experience for schools while improving operations and technology.

You'll collaborate closely with the Head of Logistics & Tutor Success and technical leadership to drive execution across the business.

We're looking for a builder, not just a manager. Someone proactive, hands-on, comfortable with ambiguity, and energized by building processes, solving problems, and scaling a fast-growing startup. This is a high-ownership environment that requires flexibility and a willingness to go the extra mile when the business needs it.

The role offers significant growth potential, including a possible path toward Head of Operations or COO.

🎯 What You'll Lead

1. Customer Success & Student Outcomes

• Build and lead Customer Success and Student Success, from onboarding through retention, renewals, and expansion.
• Develop scalable customer communication, health tracking, and risk management processes.
• Improve customer satisfaction, engagement, and student outcomes.
• Coordinate with academic, logistics, and tutor teams to ensure service quality.

2. Product Management & Innovation

• Lead Product in partnership with the CEO, translating business and customer needs into priorities.
• Manage product roadmaps, requirements, UAT, launches, and adoption.
• Work with engineering and technical leadership to improve the platform and customer experience.
• Establish feedback loops between customers, Product, and internal teams.

3. Process Improvement, AI & Automation

• Identify inefficiencies and redesign workflows to reduce manual work and operational complexity.
• Implement AI tools, agents, and automations across customer-facing and internal processes.
• Build scalable solutions that support growth without proportional increases in headcount.
• Measure the impact of improvements while ensuring reliability, human oversight, and data protection.

4. HubSpot, CRM & Customer Systems

• Own and optimize CRM processes, preferably using HubSpot.
• Build workflows, automations, reporting, and customer lifecycle tracking.
• Improve Sales-to-Customer-Success handoffs, customer health monitoring, renewals, and expansion processes.
• Drive CRM adoption and data quality across teams.

5. Data & Analytics

• Develop dashboards, KPIs, and performance scorecards.
• Monitor retention, engagement, student outcomes, product adoption, and operational efficiency.
• Turn data into actionable insights and measurable improvements.

6. People Leadership & Execution

• Hire, coach, and develop high-performing Customer Success and Product teams.
• Build a culture of ownership, accountability, and continuous improvement.
• Establish clear priorities, performance expectations, and operating rhythms.
• Lead cross-functional initiatives and empower teams to work autonomously.

👤 Who We're Looking For

Required Qualifications

• 5+ years of Customer Success experience, including leadership, or equivalent entrepreneurial experience as a Founder/Co-Founder managing customers, service delivery, teams, and business operations.
• Proven experience building and leading teams.
• Hands-on experience using AI tools, agents, and workflow automation to improve business efficiency.
• Strong track record in process improvement and building scalable systems.
• Analytical skills and experience using KPIs to drive decisions.
• Experience with CRM platforms; HubSpot is preferred but not required.
• Excellent English communication skills, both written and verbal.
• Strong interpersonal and relationship-building skills.
• Entrepreneurial mindset, adaptability, and comfort in fast-paced startup environments.
• Genuine passion for education, social impact, and helping students succeed.

Strongly Preferred

• Experience in EdTech, B2B, or B2B SaaS.
• Previous Head/Director of Customer Success experience.
• Founder, Co-Founder, or early-stage startup experience.
• Experience leading Product, Product Operations, or customer-facing technology initiatives.
• Advanced HubSpot knowledge and experience implementing AI agents.
• Experience scaling teams and operations in high-growth environments.

Additional Advantages

• Background in K-12 education, tutoring, or working with school districts.
• Experience as a teacher, tutor, or educator.
• Involvement in nonprofits, social enterprises, volunteering, or mission-driven organizations.
• Experience in marketplaces or tech-enabled services.

💡 The Mindset We're Looking For

We're looking for an energetic, charismatic, and purpose-driven leader who loves working with people, takes ownership, and thrives in fast-paced startup environments. Someone proactive, hands-on, eager to grow, and genuinely passionate about the company's mission and making a meaningful impact on students' lives.

⭐ Why Join?

• Meaningful Impact: Help improve millions of students' lives.
• Work Directly with the Founder: Contribute to the company's strategy and future.
• Ownership & Autonomy: Lead key functions and build scalable systems.
• Growth: Join a rapidly expanding company with a potential path to COO.
• Innovation: Drive AI, automation, and product development.
• Compensation & Equity: Competitive compensation, performance-based incentives, and potential equity participation, depending on experience and agreed terms.