Director, Customer Success

Customer Success United States


The Customer Success team is looking for an outcomes-oriented and strategic relationship driver to serve as a Director for our Direct to Employer business. This role is a people management position and will report to the Vice President of Customer Success.

The ideal candidate will have a background in large-scale customer relationship management with demonstrated success in partnering with clients on renewal strategy and ROI realization. In addition, the Director will be responsible for hiring, training, and motivating a team in a complex and fast-paced environment. Supporting the Castlight mission and culture are key capabilities for this function.


  • Support the professional development of a team of Customer Success Managers
  • Leverage Gainsight to drive account management
  • Manage and resolve account escalations with high customer satisfaction
  • Work cross-functionally internally to advocate for the customer success team and your customer’s needs
  • Own renewals planning from scoping to contracting
  • Build on leads generated by sales and business development to determine timing for account rollout plans, business requirements, and operational specifications
  • Ability to identify additional opportunities to drive upsells and partner with sales to deliver on revenue goals


  • Strong expertise in health benefits and healthcare data (a must)
  • 5+ years of client/account management at senior level
  • Experience with direct People Management (i.e. performance evaluations)
  • Demonstrated experience managing and advising Fortune 500 accounts for both services and support
  • Excellent presentation skills, both verbal and written
  • Ability to engage interpersonally with all levels of an organization
  • Able to thrive in a matrixed organizational structure
  • Process-driven and analytical thinker
  • Strong leadership abilities including: high accountability, adaptability to a dynamic growth oriented company culture, proactive account management
  • High level of comfort with fast-paced environments
  • Strong understanding of SaaS business model
  • Strong administrative skills with demonstrated ability to consistently deliver against internal deadlines.
  • BA/BS Degree or equivalent experience

Our Values

One team. On a mission. Making things happen.

Diversity and Inclusion

The Castlight culture values and celebrates different backgrounds, perspectives, and points of view. We believe our diversity helps drive creativity and innovation. We strive to make everyone feel included, valued, and engaged; enable them to do their best work; and build their careers here at Castlight. That is why diversity and inclusion are more than just words to us. Rather, they are a commitment to a culture where employees feel respected and empowered to share their ideas and deliver the best results.

Learn more about our continuing commitment to diversity and inclusion.

Castlight Health provides equal employment opportunity (EEO) to all persons regardless of age, color, national origin, citizenship status, physical or mental disability, race, religion, creed, gender, sex, pregnancy, sexual orientation, gender identity and/or expression, genetic information, marital status, status with regard to public assistance, veteran status, or any other characteristic protected by federal, state or local law. In addition, Castlight Health will provide reasonable accommodations for qualified individuals with disabilities.