Head of Customer Success and Support

Chalk Schools - San Francisco, CA - Full time


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Our customer success and support team is the primary source of expertise and thought leadership for schools and districts across the country as they redesign critical processes and build operational capacity for their organizations.

You will build and lead a team that helps K-12 schools and districts accomplish what they never thought possible. Define our vision for customer success and support by creating and refining key processes for onboarding, training, and professional services. Represent an innovative new brand and work closely with our sales, product, and marketing teams to develop strategies that achieve business goals and ensure success for all users.

Own key metrics for your team

  • Upsell revenue
  • Renewal and churn rates
  • Customer adoption and self sufficiency metrics
  • Account onboarding time
  • Cost / ARR ratio
  • NPS
  • Team satisfaction and projection of costs and new hires

The strategies you develop will ensure that we deliver the highest quality customer experience, not only from within the customer success and support team, but from every function within Chalk Schools.

Key responsibilities include:

  • Hire, train, and drive performance for a world class team of customer success and support specialists as they lead complex projects and technology implementations at all levels of K-12
  • Create and execute account plans that drive expansion beyond our initial footprint, manage details with big picture priorities, set best practices and expectations for our customers and team, and roll up your sleeves to personally drive key accounts
  • Create robust and proactive systems and dashboards for measuring, communicating, and escalating customer needs to cross-functional stakeholders at the company, including our sales, product, and marketing teams
  • Strategically define segmentation of our customer portfolio, structure the organization to deliver differentiated experiences, and use data to drive new and current partnerships to success
  • Work with our executive team to ensure alignment between departments, define our ideal customer experience and customer journey, and help foster a company-wide culture of customer success


  • Proven success leading teams in customer onboarding and account management
  • Proven success in creating exceptional and impactful customer experiences
  • Entrepreneurial spirit that allows you to thrive in a world of ambiguity — you know when and how to find the right information when you need it
  • Passion for our product and the value and change we seek in K-12
  • Exceptional ability to drive multiple stakeholders towards common goals through effective communication and a relentless commitment to continuous improvement


  • Experience working at an early stage, high growth startup
  • Familiarity with school system administration and operations
  • SaaS enterprise product expertise

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Customer Implementation / Customer Success

Experience Level

Senior Level

Chalk Schools

At Chalk Schools, we are committed to freeing school administrators to run their districts at their best. By bringing their mission critical processes online, districts across the country are moving away from the inefficiency and unreliability of paper with our platform. In other words, we’ve developed the first of its kind School OS.

Our diverse team comes from a variety of backgrounds but we all share a deep passion for K-12 education and bringing technology to traditionally underserved communities. Our innovative forms and workflow platform transforms the school back office and is being rapidly adopted by K-12 administrators and leaders across the country. We help schools hire the best teachers faster, manage bus routes for students with special needs, handle hundreds of chair requests during graduation season and ensure that permission slips return without requiring teachers to track down every last sheet of paper.

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