Director, Enterprise Customer Success

Newsela

11d • $120,000 - $130,000 • Remote

About The Position

We are seeking a seasoned Enterprise Customer Success Director who combines world-class customer management expertise with strong commercial acumen. This role will lead a team of Enterprise Customer Success Managers (CSMs) and own the retention and growth of our most strategic, $20MM+ Enterprise segment. You will be responsible for driving long-term value creation across our largest and most complex customers (e.g., districts with 20,000+ students). You will partner closely with Sales, Product, and Executive Leadership to ensure our enterprise clients achieve measurable outcomes while identifying and executing on growth opportunities.
In this role, you will:

Requirements

• 10+ years of progressive experience in Customer Success, Account Management, or related roles, with a minimum of 3 years managing and mentoring a high-performing team.
• Proven track record of meeting or exceeding renewal and expansion revenue targets for a book of business exceeding $10MM.
• Strong commercial instincts with fluency in enterprise buying cycles, value frameworks, and negotiation strategies.
• Executive presence and the ability to communicate complex ideas to C-suite stakeholders in large-scale Enterprise organizations (e.g., 20,000+ student districts).
• Demonstrated ability to navigate large, matrixed organizations and influence without authority.
• Willingness to travel regularly to meet with key account stakeholders
• Strong operational discipline and demonstrated experience owning revenue forecasting and renewal pipeline management.

Nice To Haves

• Experience in K-12 EdTech or broader Enterprise SaaS/technology environments.
• Demonstrated experience partnering with RevOps and FP&A to improve forecasting models and renewal playbooks.
• Strong analytical skills with comfort in financial modeling, unit economics, and data-driven storytelling.
• Familiarity with customer lifecycle tooling (Gainsight, Salesforce, etc.) and integrating these tools with other revenue systems.

Responsibilities

• Team Leadership & Development
• Lead, mentor, and inspire a team of high-performing Enterprise Customer Success Managers, fostering a culture of accountability, data-driven decision-making, and excellence.
• Manage team performance against key performance indicators (KPIs) such as Gross/Net Revenue Retention (GRR/NRR), customer health scores, and product adoption metrics.
• Drive the professional development of the team, coaching CSMs on executive engagement, complex negotiation, and strategic account planning.
• Own enterprise CS capacity planning, including headcount planning, role design, and coverage models to support segment growth and retention goals.
• Scale the team's processes and capacity to support future growth in the Enterprise segment.
• Customer Leadership & Strategic Management
• Serve as the executive-level point of contact for Enterprise customers, shaping long-term partnership strategies.
• Understand customers’ business objectives deeply and proactively guide them toward maximizing value from our solutions.
• Build and maintain trusted C-suite relationships to influence roadmaps, align on strategic priorities, and ensure renewal stability.
• Own executive-level risk escalation and intervention strategies for at-risk enterprise accounts, partnering with internal leadership to stabilize and retain key customers.
• Stay closely attuned to enterprise market trends and evolving customer needs, translating insights into expansion strategy, account planning, and Product feedback.
• Commercial Ownership & Growth
• Own the Enterprise book of business for renewals and expansion; deliver against gross and net revenue retention targets.
• Set and drive the enterprise renewal strategy, ensuring early risk identification, clear deal paths, and disciplined execution across the team.
• Identify, scope, and pursue upsell/cross-sell opportunities based on customer needs, market trends, and product capabilities.
• Partner with Sales on the co-creation of account plans with clear commercial targets and growth paths.
• Lead executive business reviews that drive strategic alignment and unlock new revenue cycles.
• Operational Excellence
• Establish and own the rigor of the renewal forecasting process for the Enterprise segment, providing reliable revenue projections to Finance (FP&A) and Sales Leadership.
• Leverage data-driven insights to forecast account health, renewal risk, and expansion potential with high accuracy.
• Build scalable processes that improve enterprise engagement, adoption, and maturity while minimizing churn drivers.
• Ensure best-in-class onboarding, value realization, and lifecycle management for enterprise customers by leveraging customer lifecycle tooling and data.
• Cross-Functional Influence
• Clearly articulate enterprise customer health, priorities, and value narratives to executive stakeholders, informing go-to-market and product decisions.
• Collaborate with Product to represent the voice of the enterprise customer and influence roadmap priorities.
• Work with Marketing and Enablement to document and communicate enterprise success stories, proven value drivers, and use cases.
• Partner extensively with Finance (FP&A) and RevOps to refine commercial models, renewal playbooks, and improve revenue projection accuracy.

Benefits

• Health & Wellness: Comprehensive medical benefits with employer contribution to premiums and to HSA accounts. Additional benefits such as pet insurance, free access to the Calm app, and more to help you stay healthy: mind, body, and soul.
• Work From Home: We are a fully remote company. We provide a monthly tech stipend to support your WFH needs!
• Supporting ALL Families: Inclusive benefits to support you and your family, including parental leave, fertility support, adoption, and more!
• Financial Wellbeing: Invest in your future with our 401(k) plan, which includes a employer match to help you build long-term financial security.
• Time Off: Flexible PTO plus 10 company holidays plus winter break (Dec 24th - Jan 1st).
• Professional Development: Newsela offers an annual learning and development allowance to employees to attend external training sessions, classes, workshops, conferences, and educational materials to foster professional growth within their current role and career aspirations at Newsela.
• Make A Difference: No matter your role or department, the work you do each day helps share the future of education and improves the lives of students and teachers.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed
• Number of Employees: 251-500 employees