Head of CS at ParentSquare

United States

About the Role We are seeking a visionary, energetic, and strategic Senior Vice President (SVP) of Customer Success to lead and inspire our entire post-sales customer organization. An exceptional customer experience is in our DNA and you will be the ultimate champion for our customers, responsible for developing the strategy and driving the execution of everything related to their lifecycle and success. You will own customer onboarding, support, success management, and professional services. The ideal candidate is a seasoned leader with a proven track record of scaling customer-facing teams in a high-growth SaaS environment, preferably within EdTech. You will be instrumental in designing and implementing strategies that leverage technology, especially AI, to drive efficiency and scale. You are passionate about building a world-class, empathetic customer experience, driving tangible value, and fostering a culture of customer-centricity throughout the entire company. Most importantly, you’re someone who shares in our passion to improve the lives of students through communication. What You’ll Do Executive Leadership: Serve as a key member of the leadership team, representing the voice of the customer in strategic discussions and contributing to the overall company strategy. Customer Advocacy: Translate customer feedback into actionable insights, driving product enhancements and influencing the product roadmap. You will also build a continuous feedback loop with product and engineering teams to enhance the customer experience. Strategic Vision: Develop and execute a comprehensive customer success strategy that aligns with company goals, focusing on driving product adoption, customer value, retention, and growth. Team Leadership & Development: Lead, mentor, and scale the customer journey through multiple product lines across Implementation, Customer Support, and Customer Success Management. Foster a culture of excellence, accountability, empathy, and continuous improvement. Operational Excellence & Scale: Define and manage the budget for the Customer Success organization. Design and implement scalable processes, systems, and playbooks to ensure a consistent and high-quality customer experience as we grow. AI & Technology Strategy: Develop and implement a strategy for leveraging technology, particularly AI and automation, to increase operational efficiency, enhance the customer experience, and drive proactive support and success motions at scale. Performance & Metrics: Own and drive key performance indicators (KPIs), including Net Revenue Retention (NRR), Gross Revenue Retention (GRR), Customer Satisfaction (CSAT), and product adoption. Cross-Functional Collaboration: Partner closely with Sales, Product, Engineering and Marketing leadership to ensure a seamless customer journey from pre-sale to renewal and to create tight feedback loops that inform the product roadmap and go-to-market strategy. Customer Relationships: Act as the executive sponsor for key strategic accounts, build relationships with customer executives, and serve as the final escalation point for critical customer issues. What We’re Looking For 10+ years of experience in customer-facing roles with at least 5+ years in a senior leadership position (VP or SVP) within a B2B SaaS company. A deep-seated passion for the customer; you are a natural advocate who lives and breathes the customer experience. Proven experience leading and scaling a Customer Success organization of 50+ people through a significant growth phase. Deep expertise in the EdTech (K-12) space is strongly preferred. A demonstrated track record of successfully owning and improving key SaaS metrics, including NRR, GRR, and CSAT. Experience managing managers and developing leaders within your organization. Experience implementing and utilizing AI-powered tools and strategies to drive efficiency and improve customer outcomes (e.g., for support automation, health scoring, proactive engagement). Strong executive presence and exceptional communication skills, with the ability to influence and align stakeholders at all levels, from individual contributors to the Board of Directors. A data-driven, analytical, and process-oriented mindset. Experience managing large, complex, enterprise-level customer relationships. Why Join Us? At ParentSquare, we believe in winning together and building a product that truly serves schools, educators, and families. We value transparency, collaboration, and an entrepreneurial spirit, and we look for team members who share these values. You’ll have the opportunity to lead design at scale, influence a fast-growing company, and make a meaningful impact on K-12 education. The perks of working for us are great! You’ll get your foot in the door as our company continues to grow. We’re big believers in work-life balance and provide: Employer-paid health insurance (including dependent coverage) An employer-matched 401K retirement savings program from day 1 Paid Parental Leave Stock options Health + wellness reimbursements Generous PTO 15 paid holidays, including your birthday! As a fully remote team, we’ll make sure you have all the tools and equipment you need to make your home office a place where you can thrive. We're an equal-opportunity employer. All applicants will be considered for employment without attention to age, race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status.