Head of Customer Success for Swing Education in San Mateo, CA

Head of Customer Success

Swing Education - San Mateo, CA - Full time

Swing Education - San Mateo, CA - Full time

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The Head of Customer Success (CS) ensures that we offer a quality experience to our pool of substitute teachers and schools partners. This role sets the vision and strategic direction of the CS team and how we provide premium customer care and education as we scale our marketplace to work with more schools and subs nationally. The Head of CS collaborates proactively with other departments to handle challenging customer cases, shares findings and best practices across the company and manages and directs the professional development of CS team. The Head of CS also advocates for the “voice of the customer,” communicating product feedback and making a strong case for school and sub needs.

An ideal candidate for this position enjoys leading and developing a team, is an excellent communicator and trainer, a constant learner, an out-of-the-box thinker, empathetic, technically-minded, and unflappable. To succeed in this role, you must be adaptive and able to work in a fast-paced, highly interactive, and innovative environment. This position reports to the Head of School Partnerships.


  • Day-to-Day
    • Personally handle challenging customer situations and high-touch escalations
    • Master and train others on the technical details of our product and Customer Success tools
    • Write clear, effective documentation for both external and internal users
  • Management
    • Manage the team responsible for training schools and responding to incoming tickets in a friendly, helpful, timely manner
    • Establish regular team meetings and 1:1 check-in’s and direct professional development of individual team members
    • Lead hiring and shape the growth of the CS team
  • Collaboration
    • Advocate for customers' needs to the rest of the company using quantitative and qualitative data
    • Set the vision for user education at Swing collaboratively with Sales and Product
    • Contribute to goals of Sales, Partnerships, Marketing, Product, Talent where appropriate
  • Strategy
    • Set and codify vision and standards for customer care at Swing
    • Define CS strategy and methods to deliver OKRs
    • Increase capacity to solve tickets by analyzing data, optimizing workflows and processes and developing scalable methods of "solving tickets before they happen"


  • Bachelor’s degree required
  • Minimum of 5 years of work experience; 2+ years’ experience customer success or experience strongly preferred; experience working in K-12 education a plus
  • Track record of excellence in team management and development
  • Naturally empathetic, motivated and excited by helping and empowering customers and teammates
  • Proactive, entrepreneurial style, eager to identify problems and work towards solutions in a fast-paced, dynamic environment
  • Data-driven decision maker with proven data analysis skills
  • Experience creating process from scratch and improving on them
  • Outstanding communication and interpersonal skills, including the ability to build relationships and collaborate with teammates
  • Quick study and effective teacher of technical concepts and systems
  • Commitment to diversity and inclusion, and enjoy working with diverse groups and teams

Swing Education is an equal opportunity employer and strongly encourages applications from people of color, persons with disabilities, women, and LGBT applicants.

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Customer Implementation / Customer Success

Experience Level

Mid Level

Swing Education

Swing Education is focused on tackling the substitute teacher shortage. We make it easy for great schools and quality subs to find each other. 

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