Account Resolution Specialist (Collections) at Olly Olly

👋 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 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 provide them with tools, strategies, and insights that help them rank higher, generate high-quality leads, get calls and reviews, and, above all, grow sustainably without the hassle.

The Olly Olly platform complements our hands-on service perfectly: it’s no-nonsense, easy-to-use software that helps local businesses streamline operations and contact management, drive leads, stabilize cash flow, and maximize revenue with minimal effort so they can reclaim their time to focus on what they do best.

🌎 Our Vision

We aim to be the ultimate all-in-one platform for small business growth, allowing owners to manage every part of their business efficiently and effortlessly.

Our journey began as an agency, and we’ve already helped thousands of clients succeed. Now, we’re embracing an exciting new chapter: becoming a SaaS-first company. By combining hard-earned human expertise with AI and automation, we’re creating affordable solutions that give business owners peace of mind while driving measurable success.

💸 The Collections Specialist Opportunity

We’re looking for a results-driven Collections/Account Resolution Specialist to join our growing offshore 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 125+ outbound calls daily to clients with delinquent accounts.
  
• 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 service role.
  
• Strong English communication skills—verbal and written.
  
• Confident negotiator with a calm, persuasive approach.
  
• Proven ability to overcome objections and de-escalate difficult conversations.
  
• Organized and detail-oriented, with experience logging activity in CRM or payment systems.
  
• Self-motivated and capable of hitting targets in a fast-paced, remote environment.

➕ Bonus Points

• Experience working with small-to-medium-sized service businesses.
  
• Knowledge of recurring/subscription billing models.
  
• Familiarity with Stripe, Profitwell, HubSpot, or similar systems.
  
• Bachelor’s degree in business, communications, or finance (preferred but not required).

🌟 What You’ll Love About Working at Olly Olly

• Compensation: $40,000 guaranteed salary paid on a weekly basis
• Schedule: Monday – Friday, 8:00 AM – 5:00 PM EST
  
• Generous PTO: 15 vacation days + U.S. holidays
  
• Impactful Work: Your efforts directly influence company growth and client success
  
• Supportive Culture: Join an international team where your voice is heard and your growth is prioritized

💡 Why Choose Us?

Join us during this exciting phase as we grow from a service agency to a SaaS-first platform. As a Collections Specialist, you’ll play a crucial role in stabilizing our revenue, strengthening client relationships, and helping small businesses thrive across the U.S!

🌈 Diversity & Inclusion at Olly Olly

We’re proud to be an inclusive employer. Diversity drives innovation, and your unique perspective helps us build better tools for real people. We welcome all voices, backgrounds, and experiences—because together, we grow stronger.