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Req # 101019

VP, Professional Services

San Francisco, CA US

Employee: Full Time Employee
Travel: 20%
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.


Castlight is seeking an experienced Professional Services leader with an operational background and successful track record of leading Professional Services teams in high growth environments delivering to large, complex enterprise customers in a SaaS environment. The VP of Professional Services will be responsible for defining the strategic direction of the services organization, and managing all aspects of new implementations and ongoing projects across our customer base.

The ideal candidate will have a history of successfully leading diverse professional services teams, implementing strategies and methodologies to ensure high quality deployments of a complex healthcare product, have a strong grasp of managing the P&L of a SaaS Services business, and the ability to maintain high levels of customer satisfaction across a wide variety of customers and implementations.

Your team will include Project Managers, Business and Technical Analysts, Configuration Specialists, and Implementation Engineers who are responsible for new customer implementations, ongoing project management, and annual customer updates and rollovers across the entire Castlight Book of Business.

  • Set the strategic direction for the professional services organization. 
  • Lead and grow a delivery organization of 50+ Project Managers, Analysts and Implementation Engineers. 
  • Establish operating practices to address scalability while working closely to develop better hand-offs and interfaces with other teams.
  • Lead from the front and provide hands-on management and oversight for your teams and key customer implementations. 
  • Provide executive sponsorship and build strong relationships with key customers, partners, and 3rd party vendors.
  • Develop and/or maintain department procedures, metrics and key performance indicators to measure operations and improvement targets to support changing business requirements
  • Partner with the Sales team and assist in project pre-qualification and scoping to ensure that high quality deals are sold that will lead to customer success. 
  • Maintain reporting on capacity, amount of implementation work, and future outlook in order to advise strategic direction setting
  • Provide Senior Leadership with regular project updates serving as a critical advisor to the team as an Implementation leader 
  • Ensure the Services organization delivers projects that meet or exceed Customer expectations

Key Requirements
  • 10+ years of demonstrated management experience in an Enterprise software environment, including SaaS, delivering to large, complex enterprise customers
  • 5+ years experience managing a services business including P&L responsibility, recruiting, training, staffing, and performance management for technical and non-technical staff
  • Proven, hands-on experience successfully implementing SaaS and/or enterprise software applications in complex, data rich environments; strong preference for experience in Healthcare and/or Wellness 
  • Excellent people management skills with the ability to lead collaboration across functions and organizations.
  • Ability to make tough decisions, to change and adapt quickly, while remaining focused on customers
  • Demonstrated ability to manage ambiguity and apply problem-solving skills to unique situations
  • Strong operational management, project management, consulting, and process improvement skills
  • Strong communication/presentation and negotiation skills.
  • Fanatical about customer success and tenacious at driving long-term customer value.

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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