We’re seeking a Director of Scaled Customer Success to transform how we support customers through digital, AI‑driven engagement.
This role will own strategic initiatives and serve as the architect of an AI‑first engagement engine designed to drive retention and product adoption at scale.
Scale the human touch: design and deploy AI-driven playbooks that automate routine success motions, including onboarding, product engagement and adoption, health checks, while maintaining a personalized feel.
Predictive churn modeling: integrate predictive AI models that identify ‘at-risk’ signals before they become churn realities.
Partner with the success team to oversee the creation of dynamic, AI-generated campaigns and automated email flows tailored to specific personas and behaviors.
Lead strategy for in-product messaging and self-service capabilities to resolve queries and drive feature adoption.
Use AI and automation to identify ‘ready-to-buy’ signals, creating automated lead generation paths.

Bachelor’s degree in Business, Technology, or related field
10+ years of experience in Customer Success, Success Transformation, or SaaS operations.
Proven track record of leading technology implementations and process improvements in a SaaS environment driving successful outcomes.
Strong understanding of customer success metrics, lifecycle management, and SaaS business models.
Excellent leadership, communication, and stakeholder management skills.
Experience with technology platforms like Salesforce, Gainsight, or the newest AI-first Customer Success Platforms.
Knowledge of automation, AI-driven customer engagement, and data analytics.
Ability to manage cross-functional projects and influence at all organizational levels.
Background in Educational Technology.
Prior management or team‑lead experience preferred, as this role is expected to evolve into a leadership position with direct reports.

Comprehensive Insurance Coverage (including Medical, Dental, Vision, Pharmacy benefits, Life Insurance and AD&D)
Flexible Spending Accounts and Health Savings Accounts
Short-Term Disability and Long-Term Disability
Comprehensive 401(k) plan
Generous Parental Leave
Unrestricted paid time off (known as Discretionary Time Off
DTO)
Wellness Program, including ClassPass & Employee Assistance Program
Tuition Reimbursement
Optional Benefits: Pet Insurance, Identity Theft Protection, Student Debt Repayment Program and Prepaid Legal coverage

Director, Scaled Customer Success

Key skills