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Customer Support Specialist II

May 15, 2026

Castlight Health is on a mission to build an integrated health network that enhances healthcare experiences. They are seeking a Customer Support Specialist II to assist health insurance members by making outbound calls, helping them navigate their healthcare benefits, and providing exceptional customer service.

Responsibilities

Represent apree health to our clients, partners, internal and external customers through best-in-class service and technological solutions
Conduct outbound calls to health plan members to assist them in finding providers, scheduling appointments
Handle inbound support calls as a flex team to support the inbound business. Inbound support may include, but not limited to digital support, appointment scheduling, and health plan support
Be a knowledge source for members for explanation of benefits, employer health incentives, and navigating the complexities of their health insurance benefits
Take ownership of resolving member concerns and healthcare navigation issues by providing end-to-end, closed-loop service
Accurately and effectively interpret, explain, identify and facilitate updates, modifications, and/or corrections of discrepancies related to medical billing, Explanation of Benefits, or other insurance-related documentation
Requires being at a desk for extended periods of time
Requires being on the phone with patients, insurance companies, providers and others throughout the day
Cameras must be on during all meetings

Skills

40 hours per week with multiple shifts from 5:45 am to 7:00 pm MT
Must successfully complete 3-6 weeks of training with 100% attendance starting on May 11th, 2025
Looking for both hybrid and remote workers (If within 50 miles of Sandy office, hybrid employee; if outside 50 miles, remote employee)
Represent apree health to our clients, partners, internal and external customers through best-in-class service and technological solutions
Conduct outbound calls to health plan members to assist them in finding providers, scheduling appointments
Handle inbound support calls as a flex team to support the inbound business
Be a knowledge source for members for explanation of benefits, employer health incentives, and navigating the complexities of their health insurance benefits
Take ownership of resolving member concerns and healthcare navigation issues by providing end-to-end, closed-loop service
Accurately and effectively interpret, explain, identify and facilitate updates, modifications, and/or corrections of discrepancies related to medical billing, Explanation of Benefits, or other insurance-related documentation
Requires being at a desk for extended periods of time
Requires being on the phone with patients, insurance companies, providers and others throughout the day
Cameras must be on during all meetings
Positive, resilient, professional, customer-focused mindset, excellent oral and written communication skills
Driven, team player, accountable for performance, behavior and willingness to be of assistance to others in navigating complex healthcare environments
Demonstrated success in a customer-focused role, with a preference for previous healthcare, call center and/or outbound call experience
High School diploma or equivalent
Attention to detail and regular attendance required (40 hours per week)
Remote employees must be free from distractions: Anything that prevents or detracts the employee from giving full attention to work
Must be able to perform all job duties
Experience with Google suite and Salesforce Service Cloud a plus

Benefits

Paid time off & paid holidays
Employer contributions for HSA accounts
6 weeks of paid training (requires 100% attendance)
Tuition assistance
Opportunities for career development and advancement
Multiple full-time shifts available within the hours of 5:45 am - 7 pm
Variable compensation includes performance based bonus opportunity

Company Overview

Castlight Health provides a healthcare navigation platform with resources for benefits, and vendors. It was founded in 2008, and is headquartered in San Francisco, California, USA, with a workforce of 501-1000 employees. Its website is http://www.castlighthealth.com. Company H1B Sponsorship

Castlight Health has a track record of offering H1B sponsorships, with 3 in 2026, 16 in 2025, 22 in 2024, 21 in 2023, 30 in 2022, 15 in 2021, 53 in 2020. Please note that this does not guarantee sponsorship for this specific role.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...