Director, Customer Success (Key Accounts)

Location: Remote/Virtual

Req #200387

The Customer Success team is looking for a Director of Key Accounts responsible for the success of a portfolio of the company's largest clients. This role is a management position and will report to the Sr. Director of Key Accounts.

The ideal candidate will have a background in large-scale customer relationship management and sales, with demonstrated success in partnering with clients to achieve their goals and in retaining and growing our relationship with them. In addition, the Director will be responsible for hiring, training, and motivating a team in a complex and fact paced environment. Supporting the Castlight mission and culture are key capabilities for this function.


  • Grow and manage a team of senior account facing professionals.
  • Grow and manage a portfolio of business with responsibility for growth and retention of existing customer base.
  • Manage and resolve escalations, including working directly with VP level and above customer contacts to build relationships and resolve issues as they arise.
  • Identify and articulate customer business objectives in order to meet and exceed them
  • 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 growing and managing a team
  • Experience with direct sales and/or managing a sales team
  • 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, proactive and thoughtful
  • 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

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.

About Castlight

Castlight is on a mission to make it as easy as humanly possible to navigate healthcare and live happier, healthier, more productive lives. Our health navigation platform connects with hundreds of health vendors, benefits resources, and plan designs, giving rise to the world’s first comprehensive app for all health needs. We guide individuals—based on their unique profile—to the best resources available to them, whether they are healthy, chronically ill, or actively seeking medical care. In doing so, we help companies regain control over rising healthcare costs and get more value from their benefits investments. Castlight revolutionized the healthcare sector with the introduction of data-driven price transparency tools in 2008 and the first consumer-grade wellbeing platform in 2012. Today, Castlight serves as the health navigation platform for millions of people and is a trusted partner to many of the largest employers in the world. We are headquartered in San Francisco, and can be found online at and on the New York Stock Exchange as CSLT.

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.

Castlight Health does not accept unsolicited assistance from recruitment search firms for employment opportunities. All resumes submitted by search firms to any employee at Castlight Health via email, the Internet or in any form and/or method without a signed search agreement on Castlight’s form in place ahead of time will be deemed the sole property of Castlight Health. In such cases, no fee will be paid or payable in the event the candidate is hired by Castlight as a result of the submission.