Collections Specialist

The role

This person will manage a high volume of outbound and inbound calls to resolve overdue balances and prevent cancellations. They will negotiate repayment plans and maintain records in internal tools.

What you will do

• Make 100+ outbound calls daily to clients with delinquent accounts on past-due invoices.
• Handle inbound calls related to billing questions, payment issues, and cancellations.
• Proactively contact clients at risk of cancellation to offer tailored solutions.
• Negotiate and implement custom repayment plans.
• Follow established procedures to collect on overdue accounts while complying with all applicable laws.
• Maintain accurate, detailed records in HubSpot, Profitwell, and Stripe.
• Partner with Account Management and Support to resolve account discrepancies or concerns.
• Track and report trends in payment issues, customer objections, and process breakdowns.

Required qualifications

• 3+ years of experience in collections, account resolution, or a similar phone-based customer-facing role.
• Demonstrated success in customer service, account management, or sales.
• Strong verbal and written communication skills.
• Ability to build rapport quickly.
• Ability to retain clients and resolve conflict under pressure.
• Highly organized with strong attention to detail and data accuracy.
• Comfortable working independently in a fast-paced, metric-driven environment.

Nice to have

• Experience working with U.S.-based clients and/or service-based businesses.
• Familiarity with recurring billing models, Stripe, Profitwell, or HubSpot.
• Bachelor's degree

Benefits

• 15 vacation days
• U.S. holidays

About the company

Olly Olly blends technology and real-world expertise to empower small businesses across the U.S. They are evolving into a SaaS-first company combining human expertise with AI.