Billing Representative

Why Clipboard Exists :

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

About Clipboard :

Clipboard 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 700+ 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 .

About the Role

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.

Responsibilities :

Monitor accounts to identify outstanding debts

Review previous data for each debt or bill

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

Identify the root cause of non-payment

Resolve billing concerns

Report on collections update and accounts receivable status

Communicate with the sales department to maintain accurate and updated information on client contract and other information

Maintain a log of calls and record any payment updates from the customer

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

Identify critical accounts and endorse them to managers as needed for proper escalatory measures

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

Build out SMART action plans for delinquent accounts

Aim to have a 95% collection rate on a quarterly basis

Requirements and Skills :

Professional and clear communication (verbal and written)

High attention to detail

Comfortable with math and data

Strong judgment in customer-facing decisions and live interactions

Mileage for feedback (high "coachability")

Ability to build relationships with customers

General professional hygiene (e.g., always on time, follows through on commitments, etc.)

Active listening

Negotiating skills

Patience and stress management

Problem-solving and critical thinking skills

Quick adaptability to changes

Preferred : experience with Google Drive suite, Slack, Salesforce, soft phone softwares like Amazon Connect

Qualifications

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.

Hiring Process

Application

Case Study

Interview 1

Interview 2

Offer

Why Join Clipboard?

100% Remote – Always. 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

System Requirements

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.

Next Steps After Application :

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.

You will receive an email with the next steps in the process within 2 days of your application.

Check your spam folder! If you don’t see the email, make sure it hasn’t been filtered out or blocked.

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