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Director, Customer Success

Pluralsight, LLC
United States
Sep 24, 2025

Job Description:

As the Director of 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.

Who you're committed to being:

  • 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

What you'll do:

  • 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

  • Experience with the office of the CIO/CTO

  • Deep understanding of change management

  • Experience with Gainsight and Anaplan

Requirements:

  • 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

  • This is a remote role; however, applicants located within 45 miles of our Westlake/Dallas, TX office should expect to work on-site Tuesday through Thursday, with remote flexibility on Mondays and Fridays. This approach enables more effective collaboration, quicker decision-making, and a stronger culture, while still providing flexibility.

  • Travel expectations differ by role. Some quota-bearing sales positions involve limited travel, while others may involve travel of up to 40%, depending on business needs.

Why you'll love working here:
  • We're a blended workplace, where team members work remotely or in a hybrid setup depending on their role and location

  • We're mission driven and guided by our culture pillars

  • 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, wellness reimbursements, Pluralsight subscription, professional development funds and more.

About us:

Pluralsight provides the only learning platform dedicated to accelerating the technology skills and capabilities of today's tech workforce. Thousands of companies, government organizations and individuals around the world rely on Pluralsight to support critical technology skill development in areas that are crucial to innovation including artificial intelligence, cloud computing, cybersecurity, software development, and machine learning. Pluralsight provides highly curated content developed by vetted technology experts, industry leading skill assessments, and hands on, immersive learning experiences designed to help individuals skill-up faster.

This role is primarily performed in an office or home office setting and involves standard computer-based work.

Bring yourself. Pluralsight is an equal opportunity employer. We evaluate qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, age, or veteran status. We also consider qualified applicants with criminal histories, consistent with EEOC guidelines and local laws.

If you need an accommodation to apply, interview, or perform essential job functions, please visit the bottom of our website to learn how to request an accommodation. Learn more about our commitment to diversity, equity, inclusion, and belonging in our DEIB Report.

The annual US base + variable range for this role is $156,000 to $207,000. Actual compensation will depend on location, skills, experience, and other factors. Additional benefits and bonuses may apply.

Please be aware of recruiting scams. We'll only contact you from an @pluralsight.com email or verified channels. We never ask for sensitive personal info or payments as part of the hiring process. All openings are posted on our Careers page.

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