ParentSquare

• Partner with GTM stakeholders to evolve lifecycle stage definitions, transition logic, and governance across the revenue funnel • Partner across GTM to map key moments in the prospect and customer journey and define what should happen at each stage • Create systems and workflows that make that journey visible and actionable • Strengthen lifecycle discipline, stage progression, and team handoffs so go-to-market teams are working from a shared understanding of intent, readiness, and responsibility • Build and optimize HubSpot workflows and automation that support lead routing, nurture, campaign operations, and follow-up • Partner with Marketing to operationalize new campaigns and motions in scalable, measurable ways • Improve motion follow-up to reflect engagement, intent, and lifecycle context • Enable insights from conversational intelligence into better signals for SDRs and leaders • Identify gaps across go-to-market processes and recommend improvements

• Partner closely with product owners, executive leadership, design, sales, and marketing to ensure we build the right things as simply as possible • Act as the internal champion for AI development practices, mentoring the engineering org on using AI to increase sprint velocity and code quality • Build and run systems that operate robustly at scale while ensuring the highest level of security • Work with leadership to build a unified technical direction and a culture of excellence and speed • Review PRs and design the future architecture of our systems

• Own the month-end close and lead revenue accounting (ASC 606) for SaaS streams • Drive the full cycle from billing to collections • Evaluate current tech stack and lead migrations • Experiment with and implement AI tools • Mentor junior staff

Who we’re looking for: ParentSquare is moving beyond traditional operations. We are scaling from "operational" to "intelligent." As our GTM Systems & Data Manager, you won't just manage a CRM; you will architect the data backbone that powers our entire revenue engine. We are looking for a technical leader who views HubSpot not as a database, but as a platform for AI-driven insight, automation, and high-fidelity forecasting. You will be one of the primary owners of the technical roadmap for Sales, Marketing, and Customer Success, transforming reactive workflows into proactive, insight-driven operations. This is a "player-coach" role where you will mentor a Systems Architect while personally designing the sophisticated data models that sustain our growth What You'll Do: - Architect for the Future: Design scalable data structures and AI-ready processes in HubSpot, Claude, Attention, and other platforms to support intelligent automation. - Operationalize AI: Own the RevOps AI roadmap, moving past the hype to build real-world routing, forecasting hygiene, and risk-detection models. - Establish Data Truth: Build a governance framework that ensures our ARR mechanics, attribution, market intelligence, and lifecycle stages are bulletproof. - Lead Technical Talent: Manage our GTM Systems Architect, establishing high standards for documentation and system integrity, and mentor the rest of the team in keeping up with new technologies and best practices. Who You Are: - A HubSpot Power User: You have deep experience in architecture, workflows, and datasets. You also have strong opinions about how AI is changing what a CRM’s role is in GTM going forward and how you want to shape the next generation of operations. - A Systems Architect: You think in terms of integrations, APIs, and multi-system dependencies, and you have the technical skillset to do this work on your own. - An AI Early Adopter: You are already experimenting with and operationalizing AI in GTM platforms to reduce manual burden, and you want to own prototyping complex agentic systems. - A Leader: You have 8+ years in RevOps or Technical Ops and have experience mentoring technical contributors 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 - PTO that increases each year - 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. We are committed to maintaining a drug-free workplace in compliance with applicable state laws. The salary range for this role will be $140,000-$180,000, DOE

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.

Who We’re Looking for Are you a teacher or school administrator who knows and loves ParentSquare? We’re looking for Summer Trainers to join our team on a temporary basis to help onboard and train our newest ParentSquare users! In this role, you’ll use your firsthand experience to guide educators and staff through the platform, ensuring they feel confident and empowered. The hours are flexible and designed to fit around your school schedule, making it a perfect opportunity to share your expertise while maintaining your summer freedom. If you're passionate about effective communication in education and want to help others succeed with ParentSquare, we’d love to hear from you! Some details: - This is a temporary contract (1099) position paid at $25/hour worked - Summer Trainers will need access to a computer and a quiet place to work; must be comfortable in front of (virtual) crowds - Hours will be allocated based on training needs and your availability; understanding this may vary week to week. - Ideally candidates are available from summer break start (May/June) through back to school (Aug/September). Additional availability through September is also highly desirable!

• Answering incoming emails, live chats and phone calls, resolving support issues quickly and efficiently and escalating tickets to the next tier of support when needed • Resolving product or service problems by clarifying the customer’s needs, determining the cause of the problem, selecting and explaining the best solution to solve the problem, expediting correction or adjustment, and following up to ensure resolution • Taking detailed notes of the contact in our ticketing system • Maintain updated knowledge of all company products and services in order to provide adequate education to customers • Collect and record customer feedback and information, and share with appropriate departments and team members • Improving help articles and developing support materials • Product testing • Contributes to team effort by accomplishing related results as needed. • Attending all required customer service-related meetings • Above all, providing the friendly and personalized service of which ParentSquare prides itself

• Architect the Scaled Journey: Design and refine a digital-first customer journey that blends automated triggers, live workshops, and community-led programming. • Drive Growth Metrics: Take full accountability for retention, health scores, and expansion revenue across the SMB portfolio. • Lead & Coach: Manage a team of four CSMs, coaching them to execute at scale while maintaining a high standard for customer outcomes. • Operationalize Success: Partner with CS Ops and Marketing to build repeatable playbooks and automated touchpoints that identify risk early and surface expansion signals. • Data-Driven Iteration: Use product usage and engagement data to continuously "A/B test" our success motions and improve efficiency. • Cross-Functional Influence: Collaborate with Product and Sales to ensure the SMB voice is heard and that our digital-first motions align with the overall company roadmap.

• Lead Traditional FP&A Processes: Own the company-wide planning and forecasting processes and perform variance analyses to drive accountability across business teams. • Act as Strategic Finance Partner: Serve as a finance partner to department leaders (Sales, Marketing, Customer Success, R&D) to manage operating expenses, develop financial models for new initiatives, and identify opportunities for efficiency and margin improvement. • Executive & Investor Reporting: Prepare and present insightful financial analysis and management reporting packages to articulate business performance, and support the leadership team with materials related to Investor Relations. • Drive System & Process Excellence: Drive continuous improvement and automation across FP&A tools and systems (e.g., ERP, planning software) to enhance forecast accuracy and reporting efficiency. • Long-Term Planning & Capital Allocation: Develop and maintain complex, integrated financial models to support long-term strategic planning.

• Play a pivotal role in amplifying the voices of ParentSquare customers. • Focus on harnessing the power of their success stories to elevate ParentSquare’s market presence. • Lead in identifying, nurturing, and promoting customer advocates. • Create compelling content showcasing ParentSquare contributions to family engagement and student success. • Partner with Customer Success, Sales, Product, Events, and Marketing to identify advocates. • Capture and develop compelling customer stories—quotes, videos, case studies, social content, and presentation assets. • Grow and engage the ambassador community through campaigns, recognition programs, and networking sessions. • Identify, prepare, and support ambassador speakers for events.