Principal Customer Success Manager
About The Position
We’re seeking a Scaled Customer Success Leader 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. We need someone who can operate independently from day one and perform at a high level with minimal oversight, with the expectation that a team will be built under them over time. We’re targeting director‑level capability now, even though the role won’t include direct reports initially, with leadership responsibilities expanding long‑term. The ideal candidate will show that “low touch” doesn’t mean “low value,” using generative AI and automation to deliver a seamless, personalized, high‑impact experience to thousands of customers at once.
Requirements
- 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.
Nice To Haves
- 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.
Responsibilities
- Digital strategy and implementation
- 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.
- GenAI content engine: partner with the success team to oversee the creation of dynamic, AI-generated campaigns and automated email flows tailored to specific personas and behaviors.
- Scaled engagement operations
- Digital journey mapping: build end-to-end digital journeys that guide customers from initial implementation to ‘value realization’ without requiring a dedicated CSM.
- In-App orchestration: lead strategy for in-product messaging and self-service capabilities to resolve queries and drive feature adoption.
- Partner with IT and Product teams to ensure seamless deployment and adoption of the Customer Success platform.
- Revenue & retention accountability
- Expansion mapping: use AI and automation to identify ‘ready-to-buy’ signals, creating automated lead generation paths.
- Change Management & Enablement
- Drive organizational change through training, communication, and stakeholder engagement.
- Foster a culture of continuous improvement and innovation.
- Analytics & Reporting
- Define KPIs and dashboards to measure success of digital initiatives and customer outcomes, including churn and adoption.
- Segment customers by risk, maturity, persona, and behavior.
- Provide insights into leadership on trends, risks, and opportunities for improvement.
- Use data to identify systemic churn drivers and design scalable interventions to support key elements of retention strategy, particularly in mid-low market customers.
- Partner with the cross-functional team to:
- Track engagement and usage signals
- Measure impact of digital programs on retention.
Benefits
- 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
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What This Job Offers
Job Type
Full-time
Career Level
Mid Level
