Collections Specialist

👋 About Olly Olly
Ready to roll up your sleeves and help transform local marketing forever? At Olly Olly, we're blending technology and real-world expertise to empower small businesses across the U.S. like never before.
We believe small businesses are the backbone of our economy. That's why we're on a mission to equip them with tools, strategies, and insights that help them rank higher, generate leads, get calls and reviews, and grow—without the hassle.
We're evolving into a SaaS-first company, combining human expertise with AI to build practical, affordable tools that help business owners reclaim their time and drive success with confidence.

💸 The Collections Specialist Opportunity
We're looking for a results-driven Collections Specialist to join our growing team. In this remote, phone-based role, you'll manage a high volume of outbound and inbound calls to resolve overdue balances, prevent cancellations, and maintain accurate, professional records.
This isn't just about collecting debt—it's about preserving relationships, solving problems, and protecting revenue. You'll need confidence, empathy, and tenacity to turn difficult conversations into client-saving solutions.

🚀 Key Responsibilities

Collections & Client Retention

• 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, understand their concerns, and offer tailored solutions to retain their business.

• Negotiate and implement custom repayment plans that align with both the client's needs and business goals.

Compliance & Documentation

• Follow established procedures to collect on overdue accounts while complying with all applicable laws.

• Maintain accurate, detailed records in internal tools such as HubSpot, Profitwell, and Stripe.

Collaboration & Continuous Improvement

• Partner with Account Management and Support to resolve account discrepancies or concerns.

• Track and report trends in payment issues, customer objections, and process breakdowns to improve future outcomes.

✅ What We're Looking For

• 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 with an ability to build rapport quickly.

• Proven 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.

➕ Bonus Points

• Experience working with U.S.-based clients and/or service-based businesses.

• Familiarity with recurring billing models, Stripe, Profitwell, or HubSpot.

• Bachelor's degree preferred.

🌟 Why You'll Love Working at Olly Olly

• Salary: $40,000 base

• Performance Bonus:

  • Collect $55K/month in past-due accounts → $10K annual bonus, paid out monthly

  • Collect $65K/month in past-due accounts → $12K annual bonus, paid out monthly

• Schedule: Monday–Friday, 8:00 AM – 5:00 PM EST (Training + Post-training)

• Generous PTO: 15 vacation days + U.S. holidays

• Real Impact: Your work directly drives company growth and client success.

• Empowered Culture: Be part of a collaborative, high-performing team that values your ideas.

• Purpose-Driven Work: Help small businesses thrive while growing your own career.