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Req # 101053

Regional Sales Manager

Chicago, IL US

Employee: Full Time Employee
Travel: 30%
About Castlight

At Castlight, our mission is to empower people to make the best choices for their health and to help companies make the most of their health benefits. We offer a health benefits platform that engages employees to make better healthcare decisions and can guide them to the right program, care, and provider. The platform also enables benefit leaders to communicate and measure their programs while driving employee engagement with targeted, relevant communications. 

To date, Castlight has partnered with more than 240 large enterprise customers, spanning millions of lives, to improve healthcare outcomes, lower costs, and increase benefits satisfaction.

The Regional Sales Manager (RSM) is responsible for leading some of Castlight Health’s most complex, and ultimately most valuable, customer relationships. The RSM 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 RSM advances the goals of both business development and sales, and works closely with both teams.

The RSM 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 RSM 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 RSM will enable Castlight to remain on the cutting edge of establishing healthcare consumerism 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.

  • 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 RSM 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 RSMs must interface with multiple groups within Castlight
  • Minimum of 3-5 years experience in sales and/or partnership development
  • Successful sales history and consistent 100% quota attainment for past 3+ years
  • Moderate travel required 
  • BA or BS required
  • MD or MBA preferred
  • SFDC Experience preferred
  • Experience in healthcare, HR / benefits 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
  • Sensitivity to large, complex business partnerships

We are Castlight and we are…


* Changing healthcare is a team sport

* Teamwork requires respect

* Direct feedback is a gift that improves us

* Diversity makes us stronger

* We take care of ourselves and each other=


* We put our mission first

* We are here to transform healthcare

* We tackle complex problems with curiosity, passion, and ambition

* We bring our best every day

* We learn and grow together


* Done well is better than perfect

* We move fast to accelerate execution and learning

* We are empowered to take action

* We own the outcome

* We win together

EEOC Statement
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.
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