Director, Professional Services

Location: San Francisco, CA

Req #200252

Castlight Health is seeking an experienced Professional Services leader with an operational background and successful track record of leading Professional Services teams in high growth environments with large, complex enterprise customers. The Director, Implementation Services will be responsible for defining the strategic direction of the services organization, managing the team that drives all ongoing projects across our customer base, and building sustainable, scalable process for the organization.

The ideal candidate will have a history of successfully leading diverse professional services teams, implementing strategies and methodologies to ensure high quality deployments of a complex product, and the ability to maintain high levels of customer satisfaction across a wide variety of customers.

Your team will include Business and Technical Analysts, Configuration Specialists, and Implementation Engineers who are responsible for ongoing project management and annual customer updates and rollovers across the entire Castlight Book of Business.


  • Set the strategic direction and drive operational excellence for the implementation services organization
  • Lead and grow a delivery organization of 20+ Analysts and Implementation Engineers
  • Establish operating practices to address scalability while working closely to develop better hand-offs and interfaces with other internal teams
  • Lead from the front and provide hands-on management and oversight for your teams and key customer implementations
  • Provide executive sponsorship and build strong relationships with key customers, partners, and 3rd party vendors
  • Develop and/or maintain department procedures, metrics and key performance indicators to measure operations and improvement targets to support changing business requirements
  • Maintain reporting on capacity, amount of implementation work, and future outlook in order to advise strategic direction setting
  • Provide Senior Leadership with regular project updates serving as a critical advisor to the team as an Implementation leader
  • Ensure the Services organization delivers projects that meet or exceed Customer expectations

Key Requirements;

  • 10+ years of demonstrated management experience in an enterprise software environment, including SaaS, delivering to large, complex enterprise customers
  • 5+ years’ experience managing a services business including recruiting, training, staffing, and performance management for diverse staff
  • Proven, hands-on experience successfully implementing SaaS and/or enterprise software applications in complex, data rich environments; strong preference for experience in Healthcare and/or Wellness
  • Excellent people management skills with the ability to lead collaboration across functions and organizations
  • Ability to make tough decisions, to change and adapt quickly, while remaining focused on customers
  • Demonstrated ability to manage ambiguity and apply problem-solving skills to unique situations
  • Strong operational management, project management, consulting, and process improvement skills
  • Strong communication/presentation and negotiation skills
  • Fanatical about customer success and tenacious at driving long-term customer value

Based in San Francisco with up to 20% travel.

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.