Billing Representative

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 Y-Combinator company 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.

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 will require cross-functional collaboration with Billing Disputes, Sales, Customer Support, and other teams to achieve the desired goals.

• Monitor accounts to identify outstanding debts.

• Call and email accounts payable contacts, administrators, and others as needed to ask about their overdue payments and upcoming dues.

• Build relationships with workplaces (e.g., properly set expectations about our billing policy, explain NET & Dispute Terms, etc.).

• Identify the root cause of non-payment and resolve billing concerns.

• Report on collections updates and accounts receivable status.

• Identify critical accounts and devise SMART action plans to address issues.

General

• Professional and clear communication (verbal and written).

• High attention to detail.

• Receptive to feedback (highly coachable).

• Preferred: experience with Google Drive suite, Slack, Salesforce, soft phone software like Amazon Connect.

Technical

• Comfortable with math and data (e.g., calculating payment plan instalments).

• Ability to build relationships with customers.

• Strong judgment in customer-facing decisions and live interactions.

• Negotiating skills.

• Open to candidates of all experience levels—what matters most is your ability to handle business customers professionally and solve problems effectively.

• No specific degree required—we care about what you can do, not just what’s on your résumé.

• 100% Remote. Work from anywhere in the world.

• Fast-Paced Startup Environment. Join a company that values curiosity, independence, and growth.

• 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.

• Opportunity to make a significant impact with our workplace customers.

To succeed in this role, you must have:

• A reliable laptop/desktop (no Chromebooks or Linux OS).

• Minimum 20 Mbps wired internet connection.

• Wired headset for clear communication.

• A quiet, distraction-free workspace.

• Stable power and internet connectivity.

1. Application form: This includes basic billing rep skill-based questions. Some questions result in automatic rejection, so please approach these with diligence as they assess your ability to handle real problems and client situations.

2. Case Study: Collections scenarios (identifying at-risk accounts, action plans, email writing)

3. Interview 1: Collections simulation

4. Interview 2: Collections simulation

5. Offer

You will receive an email with the next steps in the process within 2 days of your application. Please check your spam folder! If you don’t see the email, make sure it hasn’t been filtered out or blocked.

Quick 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 here.