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Salary: USD 110,000 - 130,000 / annual
ParentSquare (part of Remind) is a rapidly growing edtech company serving over 22 million students across K-12 schools. The company provides unified communications platforms—ParentSquare, RemindHub, Remind Chat, and SmartSites—that enable schools and families to communicate effectively and drive student engagement.
You will lead the customer success strategy and operations for ParentSquare's largest segment: over 6,000 small and single-site school districts across the country. As Director of Customer Success for SMB, you own adoption, retention, and expansion outcomes for this high-volume segment and report directly to the executive team.
Key responsibilities include:
- Own and report on adoption, retention, and expansion metrics for the SMB segment
- Design and execute the 1:many customer success motion, blending automated, digital, and live touchpoints across onboarding, adoption, renewal, and expansion
- Lead, hire, and develop the SMB customer success team; shape team structure, coverage models, and career progression as the segment scales
- Build and scale the operating model: enrollment thresholds, coverage ratios, capacity planning, and efficiency targets
- Partner with Marketing and Customer Education on workshops, community programming, and lifecycle campaigns reaching thousands of districts
- Collaborate with Customer Success Operations to operationalize the customer journey through data, signals, and automation
- Align with Sales, Marketing, and Product to identify and act on expansion opportunities
- Measure program effectiveness and direct team effort toward data-driven priorities
You will be the strategic and operational leader accountable for how ParentSquare shows up for SMB customers at scale, balancing customer outcomes with operational efficiency.
REQUIREMENTS:
- 8+ years in Customer Success or Account Management within SaaS, with direct ownership of retention and adoption outcomes
- 4+ years of people leadership, including developing managers or leading multi-layer teams
- Proven experience building or scaling a 1:many, digital-first customer success motion (automation, digital campaigns, webinars, office hours)
- Ownership of a high-volume customer segment with demonstrated operational rigor: segmentation, coverage models, capacity planning
- Comfort using customer data and usage signals to prioritize team effort and identify risk
- Strategic mindset paired with operational follow-through; ability to design systems and ensure execution
- Strong executive communication and cross-functional influence (Sales, Marketing, Product, Operations)
