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👋 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.
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