VP of Customer Success

Swing Education - San Mateo, California - Full time

About Swing:

On average, U.S. students are with substitute teachers for 5% of the typical school year. That means our students have substitute teachers for more than six months of their K-12 school career. The problem? We're suffering from a national shortage of substitute teachers.Swing Education is focused on tackling the substitute teacher shortage. We make it easy for great schools and quality subs to find each other. We help schools find qualified substitute teachers quickly and easily, and we help subs find jobs, gain experience and build their professional network.Swing is a revenue generating, Series B, Y Combinator company.

The Position:

The VP of Customer Success (CS) leads a mission critical function to ensure we offer a quality experience to our school partners and substitute teachers, and helps them maximize their experience with Swing. 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 VP of CS collaborates proactively with other departments to increase value to our customers, handles challenging customer cases, shares findings and best practices across the company and manages and directs the professional development of CS team. The VP 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 Chief Operating Officer. 


Lead our Customer Support Function

  • Drive vision of customer support, establish quarterly strategy and corresponding KPIs, prioritize work, and monitor team performance (efficiency and quality)
  • Personally handle challenging customer situations and high-touch escalations
  • Identify and drive opportunities to scale support (resources, tooling and processes) in alignment with our growth, while balancing a high level of support on both sides of the marketplace

Lead our Customer Success Function

  • Drive vision of customer success, establish quarterly strategy and corresponding KPIs, prioritize work and monitor team performance
  • Understand customer needs, identify root causes and drive solutions to increase customer time-to-value
  • Establish key metrics and processes to monitor customer happiness
  • Define and improve engagement model across customer segments
  • Work closely with Sales to drive upsell and cross sell efforts

Team Management and Development

  • Lead regular team meetings and direct professional development of individual team members (onsite and remote)
  • Proactively identify resource needs (including outsourcing where applicable), lead hiring and shape the growth of the CS team


  • Advocate for customers' needs to the rest of the company using quantitative and qualitative data
  • Work with Marketing to establish and refine customer messaging and communication
  • Work with Product and Engineering to identify and scope internal and customer facing features
  • Set the vision for user education at Swing collaboratively with Sales and Product


  • Bachelor’s degree required
  • Minimum of 8 years of work experience; 5+ years’ customer success experience strongly preferred; experience working in K-12 education a plus
  • Track record of excellence in team management and development; experience managing remote employees and outsourced providers a plus
  • Proactive, entrepreneurial style, eager to identify problems and work towards solutions in a fast-paced, dynamic environment
  • Quick study and effective teacher of technical concepts and systems
  • Experience collaborating with Product and Engineering on feature scoping and bug resolution
  • Naturally empathetic, motivated and excited by helping and empowering customers and teammates
  • Data-driven decision maker with proven data analysis skills
  • Experience creating cross-functional processes from scratch that resulted in customer or business outcomes
  • Outstanding communication and interpersonal skills, including the ability to build relationships and collaborate with teammates
  • Commitment to diversity and inclusion, enjoys working with diverse groups and teams


  • Medical/dental benefits
  • Generous PTO
  • Paid holidays
  • Stock options
  • 401k match
  • Maternity/Paternity leave benefits
  • A stocked kitchen and unlimited caffeine
  • Mission-driven work
  • Fun, collaborative, balanced culture

Short Answer Questions: In addition to your online application, please include responses to these two questions in a cover letter:

  • Describe your most challenging experience in a customer-facing situation. What was the context, how did you help the customer, and what did you learn from the experience? (250 word limit)
  • Describe an instance where you’ve contributed meaningfully to the growth of a prior organization. (250 word limit)

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

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Customer Implementation / Customer Success

Experience Level

Senior Level

Swing Education

Swing Education tackles the substitute teacher shortage by providing more subs with less overhead.

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