Two Chicks With A Side Hustle

Help patients access care by joining one of the fastest-growing FinTech startups in healthcare.

About Cherry
Cherry is a rapidly growing Buy Now, Pay Later solution designed for medical practices, from dentists to veterinarians. Founded in 2019 by Stanford entrepreneurs with a prior successful exit, Cherry is backed by top-tier investors including Kleiner Perkins and DCM. Their mission is to make healthcare services more financially accessible while helping practices grow.

Schedule

  • Full-time
  • Remote (US)
  • Monday–Friday, business hours (one weekend per month required)

What You’ll Do

  • Work with customers to resolve inquiries and collect delinquent balances.
  • Handle inbound and outbound calls with applicants, borrowers, and merchants.
  • Review accounts, execute tailored contact strategies, and negotiate repayment plans.
  • Respond to credit and chargeback disputes promptly and accurately.
  • Skiptrace accounts with missing contact information and document all borrower interactions.
  • Partner with management to improve systems and processes across the company.

What You Need

  • 1+ years of experience in collections (customer service or sales experience may be considered).
  • Proven ability to negotiate repayment plans and manage delinquent accounts.
  • Strong communication, organization, and attention to detail.
  • Ability to work independently in a fast-paced, evolving environment.
  • High school diploma or GED required; college degree preferred.
  • Experience with Excel/Google Sheets and knowledge of collections regulations a plus.

Benefits

  • $75K base pay + $25K uncapped commission potential.
  • Monthly commission payouts.
  • Medical, dental, and vision insurance.
  • Fully remote company.

Join a high-growth startup where your work directly impacts patients’ access to care.

Apply today—spots on this small but fast-growing team will go quickly.

Happy Hunting,
~Two Chicks…

APPLY HERE