Chief of Staff

Location: San Francisco, CA

Req #200410

Castlight Health is seeking a talented, energetic and resilient strategist & communicator to serve as Chief of Staff to the CEO, supporting the CEO with internal and external communications, strategy, and leadership team execution.  This role is unique; it drives key initiatives in support of and on behalf of the CEO.  At the beginning of their tenure, this individual will principally support the CEO in drafting & preparing internal updates for the company, key client communications, investor & board updates, and strategy projects.  Over time, this individual will have the opportunity to take on self-directed leadership efforts and transition into a broader role in the organization.  

The ideal candidate will be a world-class communicator, have the proven ability to work independently, pick up quickly on new things, experience at a top-tier consulting firm or similar strategy experience, and have a track record of delivering distinctive results. 


  • Executive Communication: the Chief of Staff will develop and ensure that internal company updates (conference presentations, blog posts, All Hands, etc), external presentations (client pitches, business reviews, board materials) and other CEO-driven communications meet our high bar
  • CEO Extension: the Chief of Staff will attend meetings & calls on behalf of the CEO, supporting client discussions, internal problem solving, and other key meetings as a voice of the executive suite
  • Strategy Development: the Chief of Staff will serve as a sounding board and supporter of Castlight’s strategy team and the CEO in developing Castlight’s strategy, both at the corporate and product level
  • Project execution: lead special projects critical to the success of the business

Key Requirements

  • 3-5 years of experience in a top tier strategy consulting firm is required; additional banking, corporate strategy investing or operations role at a fast growing start-up valued
  • Undergraduate degree from a top school is required, MBA or equivalent optional
  • Experience in healthcare or health technology is strongly preferred, but not required
  • Distinctive written & verbal communication skills
  • Demonstrated career progression with increasing responsibility over time
  • Strong orientation to team culture and cross-functionality
  • Capacity to become a senior leader at Castlight following the Chief of Staff role

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.