Director, SMB Customer Success — Remote Growth Leader

Rippling, Inc.; Northern (KY); Hybrid; USD 110,000 - 130,000; Full time

Benefits offered by this job

401K matching from day 1

Stock options

Health + wellness reimbursements

PTO increases annually

15 paid holidays

Job summary

ParentSquare is seeking a Director, Customer Success – SMB to own strategy and outcomes for our largest customer segment: 6,000+ small and single-site districts nationwide. You will lead the 1:many customer success motion, shape the operating model, and scale adoption, retention, and expansion across onboarding, adoption, renewal, and expansion.

You will build and grow the SMB customer success team, define structure and coverage, and partner with Marketing and Education teams to deliver

Qualifications

• 8+ years in Customer Success or Account Management within SaaS.
• 4+ years in people leadership.
• Experience building or scaling a 1:many, digital-first customer success motion.
• Experience owning outcomes for a high-volume segment.
• Comfort using customer data and usage signals to guide priorities.
• Strategic mindset with proven execution.
• Strong executive communication and cross-functional influence.

Responsibilities

• Own adoption, retention, and expansion outcomes for our SMB segment; report to executive leadership.
• Set the strategy for our 1:many motion using automation, digital campaigns, onboarding, renewal, and expansion.
• Lead, hire, and develop the SMB customer success team and define structure and coverage.
• Scale the operating model: enrollment thresholds, coverage ratios, capacity planning, efficiency targets.
• Partner with Marketing and Customer Education on workshops and lifecycle campaigns reaching thousands of districts.
• Work with CS Operations to operationalize the journey through data and signals.
• Align with Sales, Marketing, Product on expansion signals and actions.
• Measure program effectiveness and drive improvements based on data.

Skills

Customer Success

Account Management

Leadership

Data-driven

Executive communication

Strategic thinking

Cross-functional collaboration

Job description

ParentSquare is seeking a Director, Customer Success – SMB to own strategy and outcomes for our largest customer segment: 6,000+ small and single-site districts nationwide. You will lead the 1:many customer success motion, shape the operating model, and scale adoption, retention, and expansion across onboarding, adoption, renewal, and expansion.

You will build and grow the SMB customer success team, define structure and coverage, and partner with Marketing and Education teams to deliver