Director, Customer Success

Everway

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About The Position

As the Director of Customer Success, you will lead the strategy, operations, and innovation behind how Everway supports and engages thousands of education customers in a pooled, one-to-many, and just-in-time model. You’ll be responsible for driving proactive, data-informed success programming that enhances customer value, adoption, and retention across the long tail of our K–12, Higher Ed, and State-level accounts in North America. This role will work closely with CS leadership, Product, Marketing, and Sales to ensure our high-scale engagements (e.g., digital campaigns, success plans, just-in-time nudges, webinars) are both customer-centric and aligned to our broader GTM strategy. You will also be accountable for leading a team of pooled success managers and/or program managers, building systems and processes that scale with our customer base.

Requirements

• 8+ years in Customer Success, Account Management, or Customer Marketing
• 3+ years in a leadership role, ideally in SaaS or EdTech.
• Demonstrated experience building or leading scaled or tech-touch CS programs (email automation, onboarding journeys, webinars, digital success planning, etc.).
• Strong strategic and operational acumen with ability to build for scale, optimize customer journeys, and align systems and teams around measurable outcomes.
• Skilled in CS technology platforms such as Gainsight, Salesforce, ChurnZero, HubSpot, or Totango.
• Exceptional communicator and cross-functional collaborator, especially with Product, Marketing, and Sales counterparts.
• Proven ability to use data and customer feedback to design and iterate on programs that drive business impact.

Nice To Haves

• Knowledge of the North American education market, including K–12 public, charter, and/or higher education institutions.
• Experience designing or overseeing customer communications, webinars, or scaled learning experiences.
• Familiarity with universal design for learning (UDL), assistive technology, or accessibility best practices is a strong plus.
• Background working within a pooled/scaled CSM team, digital success program, or shared inbox support model.
• Bachelor’s degree or equivalent in Education, Business, or a related field. Advanced degree a plus.

Responsibilities

• Design and execute the scaled customer success strategy across North America
• Education, supporting thousands of active accounts through digital, pooled, and tech-touch engagement.
• Lead, coach, and develop a high-performing team responsible for proactive outreach, usage enablement, success planning, and risk mitigation in a pooled delivery model.
• Build and optimize standardized workflows, playbooks, and risk intervention models that improve consistency, reduce friction, and support scale across customer segments.
• Partner cross-functionally with Marketing, Product, Enablement, and CS leadership to deliver integrated customer journeys, onboarding programs, and engagement campaigns that drive adoption and retention.
• Own the strategy for usage stimulation, segmentation, and just-in-time digital touchpoints—ensuring every customer receives the right level of engagement at the right moment.
• Leverage data, customer feedback, and cross-functional input to design and continuously improve scalable success programs, customer lifecycle experiences, retention programs and programs that unlock expansion and growth opportunities for CSMs.
• Drive operational excellence through automation/AI, streamlined systems (e.g., Gainsight, Salesforce, Pendo), and tooling enhancements that increase CSM productivity and customer value. Partner closely with the systems and customer success teams to ensure proper tool adoption, workflow automation and system documentation is followed.
• Champion a culture of experimentation and shared learning—modeling scalable practices and supporting peer enablement through documentation, training, and coaching resources.
• Monitor key KPIs including retention, health scores, verified outcomes, and engagement volume; use leading indicators to drive accountability and forecast business impact.
• Act as a customer advocate in internal forums, surfacing systemic opportunities to improve product experience and long-term value.

Benefits

• Join our team and enjoy a competitive salary with bonus opportunities, flexible work schedules, and comprehensive health and wellness benefits.
• We offer flexible time off plans, career growth through development programs, and a collaborative, innovative culture where your ideas matter.
• Ready to make an impact? Apply today and be part of a company that invests in your success!

What This Job Offers

• Job Type: Full-time
• Career Level: Director