VP, CS & Operations

ParentSquare is a rapidly growing Santa Barbara-based company that’s changing the way schools and parents communicate every day. Sound simple? We strive to keep it that way! Our mission is to give schools the power to incredibly enhance family engagement for all students. ParentSquare and RemindHub, our flagship products, serve over 22 million students and drive our mission by providing unified communications tools -forms, sign ups, payments, RSVPs, direct messaging, language translations, chat and more. Remind Chat, our free product, reaches over 80% of K-12 students, providing a safe and easy-to-use platform for direct communication between teachers and families. And our latest innovation, SmartSites, offers state-of-the-art websites for school districts, enhancing their online presence and accessibility. 

We are not just creating a product; we are creating empowered educators and engaged parents to improve the lives of all students.  We are passionate advocates for our  customers and for our employees and we invite you to join us on this exciting journey.

Who We’re Looking For

ParentSquare’s customer experience is at the core of all that we do and we are seeking a dynamic, experienced, and highly strategic leader to join our team as the VP of Customer Success & Operations. You are someone with customer advocacy in your DNA and a passion for leading teams to be true champions for the customers and families we serve. 

In this pivotal role, you will lead the charge in managing key operational teams, including our Implementation Team, Integration Services, and the Remind Operations Team, which handles support and implementations for Remind customers. You will combine strategy, execution, and mentorship to scale our operations, optimize processes, and drive successful product adoption. You are someone with the  proven ability to lead and develop high-performing teams, manage technical escalations, drive innovation (leaning into AI) and build a culture of customer-centricity that directly impacts our continued success and support our mission of improving the lives of students.

Responsibilities of this role: 

• Strategic Leadership & Vision: Lead Customer Support (outsourced internationally) and post-sales operational teams for both the ParentSquare and Remind customer base.
• Operational Excellence & Scalability: You will scale our systems and refine key processes—from onboarding and technical support to escalations to invoicing and renewals—to ensure efficiency, repeatability, and a seamless experience for our customers as we grow
• Performance & Data-Driven Management: Refine, monitor, and report on the key performance indicators (KPIs) that include implementation timelines, adoption rates, satisfaction scores (CSAT/NPS), and retention. Leverage data to drive decisions, manage team performance, and implement strategic initiatives that enhance the efficiency and effectiveness of every customer interaction.
• Cross-Functional Collaboration & Influence: Partner with Product, Engineering, Sales, and Marketing leadership to find ways to build efficiencies in our post-sales customer processes and experience. 
• CS Technology & Innovation: Take the lead in overseeing our Customer Success technology stack (e.g., Zendesk, Gainsight, etc.); to include being the champion in  integrating new technologies, including AI, to enhance analytics, improve knowledge management, and empower the team to deliver a more intelligent and proactive customer experience

Our Ideal Candidate: 

• 8+ years of progressive leadership experience in customer operations, customer success operations, and/or implementation operations, preferably within a fast-paced SaaS or technology environment serving a large user base (e.g., millions of users).
• Proven track record of scaling operational teams, driving significant improvements in efficiency, and enhancing customer satisfaction through strategic initiatives.
• Extensive experience in customer success operations, with a strong background in process re-engineering, support leadership, and managing complex technical integrations.
• Strong understanding of AI technologies and their application in customer support, automation, and process optimization. Experience leveraging AI tools to improve operational efficiency and enhance cu