Req #201141

Head of Total Rewards

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Castlight Health is a healthcare navigation company with a strong purpose and is entering an exciting new growth phase, where we are adding new product offerings to our employer vertical, as well as expanding into new sectors such as health plans.

Reporting to the Head of HR, the Total Rewards leader acts as a close strategic partner to the HR and Castlight leadership teams to ensure all compensation (executive and broad-based) and benefits programs align with the strategic goals of the company. This leader will support Castlight’s high-performance culture by rewarding and attracting top talent, creating a rewards philosophy aligned towards driving key performance outcomes. This leader will direct the planning, design, implementation, maintenance and administration of all compensation and benefits programs in order to maintain Castlight’s objectives as the company continues to transform and grow. This role is responsible for leading our benefits and well-being programs, including our own instance of our product, Castlight Complete. This leader will possess strong executive presence as they will interact extensively with the Executive Leadership and the compensation committee.


  • Oversee executive compensation, including working closely with the Head of HR to create Compensation and Talent Committee materials for the Board
  • Develop agenda topics and materials for the Compensation Committee of the Board of Directors. Lead Compensation Committee discussions along with CPO
  • Standardize executive compensation, equity planning and incentive payouts ensuring alignment with business objectives and market benchmarks
  • While teaming with HR leaders and external consulting partners, validate the effectiveness of plans ensuring: market competitiveness, enterprise/business objectives are achieved and ability to attract/reward/retain top talent
  • Manage the architecture and delivery of all rewards programs, including our merit salary review, bonus program and annual merit equity grants
  • Remain current on industry trends, best practices, compliance, new/progressive processes, etc. that enable Castlight to achieve higher levels of organizational excellence
  • Relentlessly drive operational excellence and innovation in all areas of responsibility
  • Strategize and implement Castlight’s employee retention and recognition programs
  • Serve as the compensation expert and partner with Executives and the HR Business Partners in developing rewards solutions
  • Responsible for HR analytics to drive data-driven Talent strategies and decisions
  • Accountable for Castlight’s benefits and well-being programs, including our annual benefits renewals and using our own product to enable our employees and their families to navigate healthcare
  • Be a champion and an internal client for Castlight’s products
  • Administer Castlight’s 401(k) and chair the 401(k) committee
  • Deliver various rewards and talent related trainings for manager and leader enablement


  • 10+ years’ experience in progressive total rewards roles, with a focus in compensation
  • Demonstrated ability to anticipate future trends/consequences and create innovative strategies. Bring a fresh perspective, though have deep compensation and benefits experience in a customer-focused environment.
  • An experienced program manager and thought leader. Pro-active and results oriented and capable of operating successfully in a growing organization.
  • Able to evaluate, design and recommend compensation programs based on market assessment and business strategy.
  • Systems savvy, with experience using Workday
  • Knowledge of benefit and well-being programs
  • Knowledge of healthcare and/or digital health strongly preferred
  • Accountable, proactive and thoughtful with high attention to detail and strategic problem-solving skills
  • Strong excel and presentation skills
  • Sales compensation experience desired
  • BS/BA required, or equivalent experience

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.