Chief of Staff at Castlight Health

Castlight Health

Chief of Staff

Executive Management | United States


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

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