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Summary

Lead the design and execution of scaled customer success strategy for Everway's K–12, Higher Ed, and State-level education accounts across North America, managing thousands of customers through pooled, digital, and tech-touch engagement models. Drive proactive, data-informed success programming that enhances adoption, retention, and expansion while leading a high-performing team of success and program managers.

Key Responsibilities: Design and execute scaled CS strategy supporting thousands of accounts through digital and pooled delivery; lead and develop a team responsible for proactive outreach, success planning, and risk mitigation. Build standardized workflows, playbooks, and automation systems; partner cross-functionally with Product, Marketing, and Sales to optimize customer journeys and monitor KPIs around retention, health scores, and engagement.
Skills & Tools: Strategic and operational expertise in building scalable CS programs with proficiency in platforms like Gainsight, Salesforce, and ChurnZero; strong data analytics capabilities and ability to design customer communications and digital touchpoints. Exceptional cross-functional collaboration, communication, and customer advocacy skills with demonstrated ability to drive business impact through experimentation and continuous improvement.
Qualifications: 8+ years in Customer Success, Account Management, or Customer Marketing with 3+ years in a leadership role, preferably in SaaS or EdTech. Proven experience building or leading scaled tech-touch CS programs with strong strategic acumen and ability to design programs that drive measurable outcomes; knowledge of North American education market is desirable.
Location: Remote, USA
Compensation: Not provided by employer. Typical compensation for this role is $140,000 – $180,000/year based on title, seniority, and location.

Job Description

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.

Main 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.

Essential Criteria 

  • 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.

Desirable Criteria

  • 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.

Please Submit your application by Friday 24th October 2025.