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Req # 101088

Manager, Inside Sales - 50% Remote work opportunity!

San Francisco, CA US

Employee: Full Time Employee
Travel: 50%
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.

We are seeking an Inside Sales Manager (ISM) who is in San Francisco, CA or in a nearby state and able to be in San Francisco every other week. The ISM reports to the Inside Sales Director and will lead a team of approximately 4-6 Inside Sales Representatives (ISRs). The ISRs are tasked with setting up meetings with prospects, brokers and consultants for our field sales team. Those meetings will lead to opportunities that progress through the sales funnel.

The ISM will help Castlight meet its corporate objectives, foster an even greater working relationship with our field sales partners, and help ISRs reach their highest potential. The individual that will excel in this role is used to a start-up environment, thrives on a fast-paced tempo, has a strong work ethic, exceeds expectations, is flexible, nimble and able to continually course correct, respects and cares for each member of the team, is organized, accountable, and hard-wired for success.

Responsibilities include, but are not limited to:

  • Provide leadership and oversight to your Inside Sales team on a daily basis by creating a productive, inspirational/motivating and fun environment. 
  • Train and coach new and existing ISRs on the fundamentals of prospecting, including: account research, the acquisition of key contacts, cold calling techniques and refinement suggestions, email prospecting, business building ideas, creation and execution of mini-campaigns, effective strategies for penetrating key accounts, and coaching on how to effectively partner with field sales. Help the ISRs continue to learn, grow, stretch and develop. 
  • Ensure that your team has the training and support needed to meet their individual monthly goals. Supervise and monitor daily prospecting activities and progress toward monthly goals, quarterly targets and annual objectives.
  • Provide performance updates for the overall team including forecasting, measuring to goal, analysis and reporting on the progress the Inside Sales team is making on all Key Performance Indicators.
  • Oversee database management through This includes, but not limited to appropriate triggers and reports for data cleansing, quality assurance, lead management, segmentation, data quality, etc.

  • 2 - 4 years proven track record managing employees in an inside sales environment and consistently leading the team to overachievement of goal.
  • Broad sales experience with a firm command of sales strategies, practices and tactics. 
  • Experience working in a fast-paced start-up environment.
  • Extensive experience with, Excel, pivot tables, and metrics reporting.
  • Extensive experience with Sales tools such as LinkedIn, Outreach,, InsideView, Judy Diamond, etc. 
  • Solid understanding of sales and marketing concepts, including lead management processes, customer lifecycle, account based marketing and lead nurturing.
  • Strong oral and written communication skills and experience giving effective presentations to small and large groups.
  • Strong organizational and time management skills with an innate ability to prioritize.
  • Key traits: organized, highly motivated
  • Ability to travel - 50% if not already in San Francisco
  • Digital health, software, or healthcare industry experience
  • Bachelor’s degree required.

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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