Principal Site Reliability Engineer

Location: San Francisco, CA

Req #200029

The Resilience Engineering group is a team of engineers with relationships across the company. Our goal as SREs is to provide a support structure for Engineering and enable problem-solving as well as assist in operational tasks. We have team members in San Francisco, Colorado, Sunnyvale and India collaborate to ensure long-term scalable solutions.


  • Building out and automating our world-class infrastructure both on AWS and our Datacenter.
  • Creating packaging and deployment tools, to allow engineering teams to deploy and maintain their services.
  • Automating the scaling, monitoring, and resilience of our platform.
  • Fostering relationships within engineering to provide service level performance analysis
  • Performing and developing toolsets to handle operational tasks as required
  • Mentoring and guiding internal and external team members to become collaborative, cross-functional engineers
  • Having Fun while working to nurture healthier, happier employees both at Castlight and our customers.


  • Experience in a Principal, Lead or SME position within an SRE team.
  • Proficient oral and written communications skills.
  • Collaborates well across multiple teams.
  • Ability to develop and support relationships to understand Engineering and Resilience needs.
  • Hands-on experience with Chef/Puppet (community contributions a plus).
  • Adept at automation, especially in Bash/Ruby/Python.
  • Well-versed in Linux administration and first-hand exposure to Kubernetes/Docker.
  • A deep background in working in VMWare DataCenter Infrastructures.
  • Understanding of monitoring principles and use of alerting tools such as Datadog, Nagios.
  • Values good debugging skills and will work with and mentor others to investigate operational issues.

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.