ParentSquare

Compensation

Full Description

The Opportunity We are seeking a results-oriented and customer-centric manager to scale and help lead our Small-to-Medium Business (SMB) Customer Success team. This is a newly created, foundational leadership role designed to help architect the future of how we serve our SMB customers. Your mission will be to develop a scalable, tech-forward engagement model that drives product adoption, uncovers expansion opportunities, and maintains our world-class 95%+ gross retention rate. You will lead a team of CSMs, blending automated outreach with targeted, high-value interactions to achieve ambitious growth targets, including $3M in closed-won upsells from a $6M pipeline. This is a unique opportunity to build a critical function from the ground up, directly impacting our company's growth and our customers' success. What You'll Do Lead & Develop: Recruit, coach, and mentor a high-performing team of CSMs, fostering a culture of accountability, collaboration, and customer advocacy. Architect Scaled Programs: Design and implement a tech-enabled strategy for customer engagement, utilizing automation, digital campaigns, webinars, and health checks to efficiently serve our SMB customers. Drive Revenue Growth: Own your team's commercial goals, guiding the strategy for identifying and converting upsell and cross-sell opportunities within our highest-potential SMB accounts. Maintain Excellence: Uphold and improve upon our 95%+ gross retention rate by ensuring customers derive maximum value from our platform. Own Strategic Accounts: Act as a player/coach by directly managing a small portfolio of highly influential SMB customers, modeling best practices and staying connected to customer needs. Collaborate Cross-Functionally: Partner closely with Sales, Support, Product, and Marketing to create a seamless customer journey and champion the needs of the SMB segment. Analyze & Iterate: Use data to measure the effectiveness of your programs, reporting on key metrics like retention, expansion, and customer health to inform strategy. What You'll Bring 2+ years of people leadership experience, with a proven track record of hiring, coaching, and developing high-performing Customer Success or Account Management teams. Demonstrated success in leading a team to meet and exceed commercial targets, including renewals, expansion quotas, and pipeline generation in a SaaS environment. Deep expertise in the SMB market, with hands-on experience building and executing scaled engagement strategies (e.g., one-to-many campaigns, digital touchpoints, office hours). A strategic mindset with experience leveraging technology, automation, and/or AI to drive CSM efficiency and customer value. Strong analytical skills with the ability to translate data into actionable insights and strategic initiatives. Exceptional communication and collaboration skills, with the ability to work effectively across all levels of the organization. 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.