Director of Customer Success (Remote)

Salary: Competitive Salary
Job Type: Full time

Website Upswing

Health, dental, and vision coverage, 401k program, Unlimited PTO and flexible working hours.

Director of Customer Success (Remote)

Director of Customer Success | Upswing | USA |

About Us

Upswing is a mission-driven company that partners with colleges and universities to improve nontraditional student outcomes. Over 28% of students using Upswing are working while in college, and 43% are Hispanic or Black, and many are first-generation students. Our platform doesn’t cost students a thing; the school enlists our help to support their students. We’re looking for individuals who care about education and equality of student resources to come join our team!

We’re currently partnered with more than 70 colleges throughout the country, where Upswing helps over 700,000 students succeed throughout college. You’ll get to work with a team of motivated, intelligent, and fun people at Upswing – all working toward the same mission of student success and retention.

As a mission driven organization, we strive to build a community inside Upswing where we are able to live our values to help our students grow and thrive. Our values represent why we do what we do and how we plan on doing it. We hope to build a team that represents these values so that we can all grow together:

  • Celebrate Concrete Roses
  • Dare to Fly First
  • Choose the Harder Right over the Easier Wrong

About the Role

Upswing’s Customer Success team is made of Higher Education Retention Officers, or HEROs, for short. We view the HERO team as a unique competitive advantage, as we work with our college partners to ensure their success by building up strong, consultative relationships that will help each partner navigate software challenges like implementation, change management, user adoption, and engagement.
As the Director of Customer Success, you’ll be leading our team of HEROs to ensure strong relationship building through excellent communication, consultative approaches to new software adoption, and support for the many facets of the higher education admin role that occurs throughout a school year.

About You

  • You are just as much about people as you are about processes. You are an empathetic and motivating leader who listens first.
  • You approach work as a collective challenge that involves leaning into and supporting various team members.
  • You believe in leading alongside, not leading in front, so you’re comfortable owning key accounts while also leading and managing the team.
  • You are skilled in taking things from zero to one, with an ability to take in feedback and iterate over time.
  • You have a strong mix of qualitative and quantitative leadership traits, from relationship-building to revenue planning.

Key Responsibilities

  • Oversight of key accounts
    • You will work directly with several key accounts
  • Customer Success team leadership
    • Direct supervision over Customer Success team members
    • Perform management functions including 1-1s, annual reviews, career growth, and performance improvement
    • Lead weekly account review and Customer Success team meetings
    • Provide ongoing training in various areas of the Customer Success role
    • Career development for HERO team, including hiring, career planning, and performance management
    • Cross-team collaboration for process improvements
  • Ownership of new partner onboarding process
    • Technical implementation process ownership
    • CSM communication throughout onboarding
    • Refinement of recurring technical implementation components
  • Ownership of Renewal and Upsell Pipeline
    • Ownership over team renewals and upsells
    • Collaborate with VP of revenue on quarterly goal planning and strategy
    • Review goals, pipelines, and progress with team members
    • Oversee proposal and contract distribution


  • 3+ years working in B2B SaaS customer success
  • 2+ years of people management experience
  • You are passionate about education and have experience in higher education EdTech
  • You thrive in a leadership environment that involves building and refining processes
  • You have a track record for revenue attainment and team excellence

Employee Benefits

  • Competitive salary and vested equity
  • Commission earnings (individual and team-based)
  • Medical, dental, and vision insurance
  • 401k program
  • Flexible vacation policy
  • Fully remote culture so you can work from anywhere
  • WFH stipend to make your space work for you
  • Passionate and mission driven team focused on helping making educational resources more widely available for those who need it

Tagged as: remote, remote job, virtual, Virtual Job, virtual position, Work at Home, work from home

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