Req #201147

Head of IT & Business Systems

San Francisco, CA
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Senior Director – Business Technology

Castlight is on the lookout for a technology leader to help support and grow our business technology capabilities, working across the organization on a wide variety of projects as we expand access to healthcare and people’s understanding of the health resources available to them. 

About the Role:

  • Ensures that the technology we adopt enables internal teams to be at their best
  • Rationalizes technology decisions to help us optimize our operations as we take on some of the most challenging and complex customer engagements
  • Curates a complete roadmap of technology and process iterations to support our business partners
  • Facilitate user journeys that ensure our staff has purposeful, enabling technology experiences during their time at Castlight 
  • Partner with lines of business to define and socialize the multi-year IT strategy to support Castlight’s next chapter of growth, focused on improving scale, experience and efficiency
  • Lead delivery of  portfolio, Program & Vendor Management for the IT and Engineering functions
  • Manage business expectations, drive capacity planning and prioritize resource allocation based on Castlight’s vision and growth strategies
  • Manage all internal software spend and formulate strategies to drive efficiencies
  • Influence and provide specific guidance for the development of new or improved processes aimed at enabling scale and increasing efficiencies
  • Champion efficiencies, automation and the use of data to measure, track and make decisions
  • Hire, develop, and retain extraordinary talent to scale and meet business demands while developing talent to ensure a durable succession plan
  • Develop strategies and implement roadmaps to make IT successful by embracing a product-oriented delivery model
  • Define, manage, and report on key performance indicators that measure ITs performance against corporate objectives


  • Bachelor’s or Master’s degree in computer science, business administration or related field, or equivalent work experience
  • 20 or more years in IT and business/industry
  • A minimum of 8-10 years of leadership responsibilities
  • 10+ years’ experience leading engineering and operations teams with a track record of success with strategic and complex projects
  • Expert level knowledge of the Portfolio & Program Management function and how it can best serve product and technical delivery teams in IT spanning Infrastructure, Applications, Data & Architecture
  • Experience leading teams in a fast-paced Agile software delivery environment
  • Demonstrable experience coaching and developing teams to meet career objectives
  • Hands-on experience developing and successfully rolling out internal processes which create or strengthen organizational and team efficiencies.
  • Change management expert; able to bring others along a journey of change
  • Skilled in how to best provide transparency, on-going status and portfolio management
  • Expert at collaborating and building trusted partnerships across IT, Business stakeholders, SI partners and application vendors
  • Excellent executive presence
  • Able to promote creative thinking beyond the boundaries of existing industry practices
  • Understand how to connect, listen, and engage at all levels of the organization in order to create loyalty, trust, and a following
  • Holds self and others accountable; able to inspire people to go beyond and grow
  • Leadership: Proven ability to build, develop and lead teams and rally organization around the vision
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.