As the Director of Commercial Customer Success, you will own developing and driving overall customer success strategy and renewal ARR across thousands of customers. You will drive a strategic vision for Pluralsight within the customer base to drive adoption and value realization at scale. In this role, you’ll be responsible for guiding and coaching Customer Success Managers on success planning, adoption strategies, and customer critical issues. You’ll also work with peer sales directors, global CSM directors and VPs to drive renewals and expansion opportunities to achieve best-in-class gross and net retention targets.


What you’ll do:

  • Empower and encourage your teams to drive towards targets while also focusing our customers
  • Drive and develop new initiatives and other key programs as required to evolve our Customer Success strategy. Particularly focused on a balance of human lead and digitally lead engagements.
  • Ensure alignment of strategy/approach between Sales and Customer Success
  • Meet and exceed Net Retention and Gross Retention goals
  • Support operations on behalf of your segment, such as forecasting, recruiting, training, quality assurance, CSM capacity, and customer feedback
  • Monitor and measure customer health and proactively mitigating risk
  • Build relationships with our top customers to foster upsell, prove value and to ultimately drive retention


Experience you’ll bring:

  • Experience in customer facing roles, preferably in the SaaS industry
  • Experience leading multiple teams who own the renewal transaction
  • Product lead growth of Digital Touch/Scale Experience
  • Direct experience negotiating renewals and driving ARR
  • Experience in working with and implementing enterprise customer success and sales processes and methodologies
  • Travel up to 30% required
  • Experience with the office of the CIO/CTO
  • Deep understanding of change management
  • Experience with Gainsight and Anaplan



  • Requires a minimum of 12 years of related or equivalent experience; or 8+ years and an advanced degree.
  • 2 years minimum experience in a leadership role


Why you’ll love working here:

  • We’re remote- and hybrid-friendly
  • We’re mission driven and values guided
  • We have a strong commitment to diversity and belonging
  • We cultivate a culture of trust, autonomy, and collaboration
  • We’re lifelong learners and champion team member growth and advancement
  • We’ve got you covered – team member benefits include competitive compensation packages, medical coverage, unlimited PTO and Summer Fridays, wellness reimbursements, Pluralsight subscription, professional development funds and more.
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