Req #201082

Regional Sales Director

Apply Today

The Regional Sales Director’s (RSD) primary focus is revenue attainment in a focused geography.  The RSD is responsible for leading some of Castlight Health’s most complex, and ultimately most valuable, customer relationships. The RSD mobilizes customers to not simply purchase Castlight products, but to advocate for business partnerships that are critical to the health of Castlight’s business. In this way, the RSD advances the goals of both business development and sales, and works closely with both teams. 

The RSD is dedicated to a group of the largest, most high profile accounts in the U.S., with the objective of inspiring a deep, long-lasting partnership in which these accounts work closely with the RSD to further Castlight’s mission. A partnership will include purchase of the product, but also entails a commitment to campaign and lobby for shared interests.

The RSD  will enable Castlight to remain on the cutting edge of establishing healthcare navigation for employers and employees. In addition to the duties and qualifications below, we are looking for colleagues with a demonstrated passion for the mission of the company.

Location: Midwest territory, remote role from Texas. 


  • Lead a sales process that results in a commitment to purchase the Castlight product
  • Seek participation in Castlight campaigns and lobbying efforts that advance Castlight interests (e.g., sharing of data from key partners)
  • Coordinate with sales team when RSD support is needed with traditional sales accounts
  • Partner with colleagues in business development to advance strategic goals
  • Build coalitions of stakeholders and coordinate a “call to action”
  • Document and communicate feedback from the field
  • Balance a proactive, passionate style with sensitivity to delicate partnership development
  • Maintain and update information in SFDC
  • Act as a true team player, recognizing that RSD’s must interface with multiple groups within Castlight


  • 7+ years experience in sales and/or partnership development
  • Successful sales history and consistent 100% quota attainment for past 3+ years
  • Moderate travel required (25-50%)
  • BA or BS required, MD or MBA preferred
  • SFDC experience preferred
  • Experience in healthcare, HR / benefits highly preferred
  • Experience building partnerships that enable significant revenue generation, and / or experience leading sales with multi-million dollar contract values
  • Fluency in relationship-building, particularly with key decision-makers
  • Ability to adapt / modulate style according to different settings
  • Excellent poise and presentation skills
  • Experience with large, complex business partnerships


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.