Senior Deal Desk Analyst

Location: San Francisco, CA

Req #200258

We are growing our team of deal development professionals at Castlight Health, and are looking for a new Deal Desk Analyst. This group is small yet high-achieving and highly visible, and every team member is critical to Castlight’s revenue growth.

Our ideal candidate will have a passion for top-line growth, a mind for balanced and creative deal-making, and the ability to understand the complexity of Castlight’s market and customer needs.

A successful candidate will be excited to build infrastructure in support of an evolving sales space, thrive in a fast-paced, cross-functional environment, and have a mix of analytic and interpersonal skills.  Responsibilities of this role include:

  • Guide Sales team on deal quality and proper deal structure, fallback positions, and executive approval during contract negotiations
  • Coordinate closely with Castlight executives from Sales, Channels, Customer Success, Legal and Finance teams and provide deal analysis and visibility into contract complexity
  • Design intelligent deal processes that allow for greater transactional volume while mitigating contracting risks
  • Rethink legacy processes to optimize deal flow and identify deal patterns for business improvement
  • Monitor quarter-end deal progress and close all bookings transactions 

Required Qualifications

  • Bachelor’s degree
  • 2+ years of work experience
  • 1+ years of work experience specifically in Deal Desk, contracting, renewals or pricing
  • Strong written and verbal communication skills, proven project management experience, and the ability to own and maintain end-to-end projects

Desired Qualifications/Experience

  • Big 4 or Consulting
  • Healthcare industry
  • SaaS
  • Salesforce

The Senior Deal Desk Analyst will report to the Deal Desk Manager, and will lead our efforts to continue streamlining our contract process, as well as break new ground in establishing innovative deal strategies for our partner-based business and renewals.



Our Values

One team. On a mission. Making things happen.

Diversity and Inclusion

The Castlight culture values and celebrates different backgrounds, perspectives, and points of view. We believe our diversity helps drive creativity and innovation. We strive to make everyone feel included, valued, and engaged; enable them to do their best work; and build their careers here at Castlight. That is why diversity and inclusion are more than just words to us. Rather, they are a commitment to a culture where employees feel respected and empowered to share their ideas and deliver the best results.

Learn more about our continuing commitment to diversity and inclusion.

About Castlight

Castlight is on a mission to make it as easy as humanly possible to navigate healthcare and live happier, healthier, more productive lives. Our health navigation platform connects with hundreds of health vendors, benefits resources, and plan designs, giving rise to the world’s first comprehensive app for all health needs. We guide individuals—based on their unique profile—to the best resources available to them, whether they are healthy, chronically ill, or actively seeking medical care. In doing so, we help companies regain control over rising healthcare costs and get more value from their benefits investments. Castlight revolutionized the healthcare sector with the introduction of data-driven price transparency tools in 2008 and the first consumer-grade wellbeing platform in 2012. Today, Castlight serves as the health navigation platform for millions of people and is a trusted partner to many of the largest employers in the world. We are headquartered in San Francisco, and can be found online at and on the New York Stock Exchange as CSLT.

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.