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Billing Representative

June 9, 2026

<h1>About Clipboard</h1>Our mission is to uplift as many communities as possible. We do this through our app-based marketplace that connects healthcare professionals with the workplaces that need amazing workers. This enables hundreds of thousands of people to achieve financial stability for themselves and their families while providing essential care to millions of people across the U.S. Founded in 2016, we are a remote-first team of over 1,000 people building a top <a target="_blank" rel="noopener noreferrer nofollow" href="https://www.ycombinator.com/topcompanies/">Y-Combinator company</a> and have been profitable since 2022. We’re the leader in Long-Term Care staffing and are rapidly expanding into Home Health, Hospitals, and more, meaning we have more work to do than people to do it, and are growing our team to support millions more people and their communities.Excited about what we're building? We'd be grateful if you'd spread the word. If you know a friend, former colleague, or someone exceptional you'd love to work with again, refer them <a target="_blank" rel="noopener noreferrer" href="https://jobs.ashbyhq.com/clipboard/form/ref-test-form">here.</a><h3>About the Role</h3>The Collections team under Billing is responsible for collecting payments from workplaces (e.g., healthcare facilities). The Billing Representative (BR) is responsible for ensuring that the assigned workplaces pay their invoices quickly and on time. Cash is the lifeline of any company. This is a very critical role to ensure that the cash flows for the company are smooth. The BR will reach out to the workplaces through phone and email to follow up on payments, get a commitment of payment ("promise to pay"), and ensure that the workplaces honor these commitments. The BR will work with the workplaces and the respective internal teams to ensure any roadblocks in collecting the payments are removed. The role would require a cross-functional collaboration with Billing Disputes, Sales, Customer Support, and other teams to achieve the desired goals. <h3>Responsibilities:</h3><ul style="min-height:1.5em"><li>Monitor accounts to identify outstanding debts</li><li>Review previous data for each debt or bill</li><li>Call and email accounts payable contacts, administrators, and others as needed to ask about their overdue payments and upcoming dues</li><li>Identify the root cause of non-payment</li><li>Resolve billing concerns</li><li>Report on collections update and accounts receivable status</li><li>Communicate with the sales department to maintain accurate and updated information on client contract and other information</li><li>Maintain a logs of calls and record any payment updates from the customer</li><li>Receive new workplace assignments to start contacting the customer to set the relationship up for success, including simply introducing yourself and collect the right information</li><li>Identify critical accounts and endorse them to managers as needed for proper escalatory measures</li><li>Build relationships with the workplaces (properly set expectations about our billing policy, explain NET & Dispute Terms, etc.)</li><li>Build out SMART action plans for delinquent accounts</li><li>Aim to have a 95% collection rate on a quarterly basis</li></ul><h3>Requirements and Skills:</h3><ul style="min-height:1.5em"><li>Professional and clear communication (verbal and written)</li><li>High attention to detail</li><li>Comfortable with math and data</li><li>Strong judgment in customer-facing decisions and live interactions</li><li>Mileage for feedback (high "coachability")</li><li>Ability to build relationships with customers</li><li>General professional hygiene (e.g., always on time, follows through on commitments, etc.)</li><li>Active listening</li><li>Negotiating skills</li><li>Patience and stress management</li><li>Problem-solving and critical thinking skills</li><li>Quick adaptability to changes</li><li>Preferred: experience with Google Drive suite, Slack, Salesforce, soft phone softwares like Amazon Connect<ul style="min-height:1.5em"><li>Generally, it's expected you can adapt to changes in technology</li></ul></li></ul><h3>Qualifications</h3><ul style="min-height:1.5em"><li>Open to candidates of all experience levels—what matters most is your ability to handle business customers professionally and solve problems effectively.</li><li>No specific degree required—we care about what you can do, not just what’s on your résumé.</li></ul><h3>Hiring Process</h3><ol style="min-height:1.5em"><li>Application </li><li>Case Study</li><li>Interview 1 </li><li>Interview 2</li><li>Offer</li></ol><h3>Why Join Clipboard?</h3><ul style="min-height:1.5em"><li>100% Remote – Always. Work from anywhere in the world.</li><li>Fast-Paced Startup Environment. Join a company that values curiosity, independence, and growth.</li><li>A Hiring Process That Rewards Skills, Not Just Experience. Every applicant gets a fair shot—our selection is based on real-world problem-solving ability, not just credentials.</li><li>Opportunity to make a significant impact with our workplace customers</li></ul><h3>System Requirements</h3>To succeed in this role, you must have:<ul style="min-height:1.5em"><li>A reliable laptop/desktop (no Chromebooks or Linux OS).</li><li>Minimum 20 Mbps wired internet connection.</li><li>Wired headset for clear communication.</li><li>A quiet, distraction-free workspace.</li><li>Stable power and internet connectivity.</li></ul><h3>📌 Next Steps After Application:</h3><ul style="min-height:1.5em"><li>The application form also includes basic billing rep skill-based questions. Some questions result in automatic rejection, so please approach these with diligence – they assess your ability to handle real problems and client situations.</li><li>You will receive an email with the next steps in the process within 2 days of your application.</li><li>Check your spam folder! If you don’t see the email, make sure it hasn’t been filtered out or blocked.</li></ul>#LI-DNIQuick Note on Scammers: Clipboard would never ask you for money or your bank details to participate in our hiring process. Report any scammers impersonating the Clipboard hiring team members <a target="_blank" rel="noopener" href="https://forms.gle/SyGaxHFbon7Hg9fW6">here</a>.

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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...