Two Chicks With A Side Hustle

Employer: Castlight Health

The Client Services Associate will manage individual projects, participate in technical project management and resolve technical issues, as well as maintain project plans for Castlight’s book of business. This role is part of the Professional Services organization and partners closely with Implementation, Customer Success, Engagement Strategy, and other members of the Client Services team, to drive positive customer outcomes and help them achieve their goals.

Our team utilizes a combination of data and best practices to provide a meaningful and powerfully relevant consultative experience. This role is ideal for someone who is looking to gain operational, technical, consultative, and customer facing skills as there is daily exposure to activities which touch upon all of these things. Additionally, working well in a team environment and having a self-starter attitude is critical. Client Services is a new division within Castlight and will require an eagerness to implement new ideas and iterate them quickly.

The Client Services team will also spend a significant portion of our business cycle planning for and executing on roll over work, which requires scoping customer decisions and changes to benefits from one calendar year to the next. Our mission is to turn our customers and end users into evangelists, achieve stellar employee engagement levels, and build scalable models that allow our customers and organization to succeed in achieving their goals. The ideal candidate thrives in a team-oriented environment and has excellent communication skills.

Note: the busy season’ for this role is November – January, when the bulk of the roll over work takes place; applicants should expect to take not more than 1-2 business days off during this period. Bring on the summer vacations!


  • Configure Castlight’s suite of Wellness and Care Guidance products using internal tools
  • Assist in investigating and solving issues related to configurations
  • Partner with internal teams to ensure understanding, complete scoping, and timely delivery of configurations
  • Continuous contribution to process improvement
  • Provide best practice guidance to customers and other internal teams
  • Run internal testing of product configurations; gather feedback from the customer and/or internal teams and implement requested changes
  • Work with third parties to define and test data integration
  • Collaborate with clients and internal stakeholders to resolve issues
  • Previous experience with people management a plus but not required


  • Self-starter with a love for driving projects to completion
  • Dedicated to high quality work and driving positive outcomes
  • Highly organized with the ability to effectively manage competing priorities and risks
  • Effective communicator, both verbal and written, that can work well with both clients and team members
  • Familiarity with Microsoft Office, Google Suite & Jira is a plus
  • Flexible, adaptable, and able to respond under the pressure of a fast-paced technology company