Customer Experience Specialist

Why Clipboard Health Exists:

We exist to lift as many people up the socioeconomic ladder as possible. We dramatically improve lives by letting healthcare professionals turn extra time and ambition into career growth and financial opportunity. We achieve this with our app-based marketplace that connects healthcare facilities and healthcare professionals, allowing professionals to book on-demand shifts and facilities to access on-demand talent.

About Clipboard Health:

Clipboard Health is a fast-growing Series C marketplace. We are a leader in our Long Term Care vertical and are expanding into several others (Dental Offices, Schools, etc).
We are a YC Top Company with a global, remote team of 600+ people. We have been profitable since 2022, and fill millions of shifts annually at partner workplaces across the US, where tens of thousands of professionals work with us every year.
We are looking for your help to keep growing so we can serve more professionals and workplaces.
To learn more about us, take a look at our website here.

Overview

📍 Remote | South Africa, South America & The Caribbean

Estimated annual compensation and start date: $10,800–$24,000 USD \ August 4th, 2025
Each candidate’s compensation offer will be based on multiple factors including, but not limited to, relevant education, qualifications, certifications, experience, and geographic location.

We’re not just supporting customers, we’re powering a movement of over 60,000 healthcare professionals on our platform. At Clipboard Health, our Worker Operations team owns every part of the worker journey. We keep our marketplace reliable, high-performing, and built on trust. At Clipboard, “entry-level” means starting on the front lines but operating with urgency, ownership, and the mindset of a future leader. We’re looking for experienced customer support professionals who want to solve hard problems, build deep operational knowledge, and eventually lead teams of their own. We want to promote internally and that goal always starts with you.

Many of our current leaders started right here, if you’re driven, sharp, and not afraid to grow from the ground up, we want you.

Important Note: We operate 24/7. Each shift consists of 5 days within a 7 day cycle (Sunday to Saturday), with both Saturday AND Sunday availability required to support our peak times and shifts are assigned based on business needs.

Must haves

  • Fluent, professional-level English (spoken and written)
  • 4+ years of experience in customer support via chat or voice
  • 4+ years using CRMs like Zendesk or Salesforce
  • 4+ years using Google Workspace (Docs, Sheets, Gmail, etc.) in a work se
  • An ability to thrive in fast-paced, cross-functional environments
  • A proactive problem-solver who takes initiative without waiting for direction
  • Strong attention to detail and sound judgment, especially under pressure
  • A collaborative attitude that contributes to team success

Your Responsibilities

  • Deliver fast, accurate, and empathetic support to healthcare professionals across chat, voice, and email, resolving shift, payment, and platform-related issues in real time
  • Navigate tools like Zendesk and Salesforce to investigate cases, update form fields, log clear internal notes, and maintain accurate documentation
  • Apply sound judgment and critical thinking to troubleshoot issues, follow or adapt workflows, and escalate only when necessary
  • Personalize communication using macros, proofread carefully, address workers by name, and maintain a confident, helpful tone
  • Monitor trends and flag recurring issues or process gaps to improve worker experience and internal operations
  • Support onboarding by guiding new workers through platform workflows and helping them gain confidence quickly
  • Uphold our values such as unreasonably fast, ownership, and uncomfortably high standards in every interaction

System Requirements

  • Minimum 15Mbps wired internet connection
  • Minimum i5 processor or equivalent
  • Minimum 12GB Ram
  • Quiet working environment
  • Steady power and internet connection
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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...