Billing & Accounts Receivable Specialist at Olly Olly

Given that this position requires English proficiency, we are only considering CVs provided in English. Thank you, and we look forward to your submission!

👋 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.

🫵 Why We Need You

We’re looking for a Billing & Accounts Receivable Specialist who will be both a strategic problem solver and hands-on operator in our billing and AR functions.

The ideal candidate is someone with GRIT—a problem-solver who thrives in a fast-paced, ever-evolving environment and isn’t afraid to dig into the details while also building for scale.

🚀 The Impact You’ll Have

• Support the AR team in executing day-to-day billing operations, including invoicing, collections, and dispute resolution.
• Maintain and optimize the full billing lifecycle—from subscription setup to revenue tracking and reporting.
• Execute and maintain efficient workflows in HubSpot, including automation of billing tickets and internal communications.
• Process payments and manage reconciliation activities in Stripe, ensuring accuracy and timeliness.
• Administer PandaDoc contract workflows, ensuring documentation is complete, accurate, and compliant.
• Partner with Sales, Customer Success, and Product teams to ensure subscriptions and billing details are updated correctly and promptly.
• Collaborate with the Accounting team on month-end close activities and revenue recognition support.
• Identify opportunities for process improvements and contribute to documentation and implementation of scalable solutions.
• Serve as a subject-matter expert on billing tools and processes, offering insights and support to cross-functional stakeholders.

✅ What We Really Need From You

• 3+ years of experience in billing operations, accounts receivable, or subscription-based businesses
• Strong knowledge of HubSpot (ticket automation), Stripe, and PandaDoc.
• Experience handling billing disputes, collections, and contract management.
• A proven ability to work in a high-growth, fast-paced environment with resilience and adaptability
• A problem-solving, solutions-oriented mindset with a strong bias for action.
• SaaS and services industry experience preferred.
• Strong analytical skills and comfort working with spreadsheets to analyze revenue data.
• Ability to collaborate with leadership and cross-functional teams to drive operational improvements.

➕ What Would Be Big Pluses

• Experience handling customer service calls and collections.

This role is hands-on and high-impact—ideal for someone who’s detail-oriented, resourceful, and thrives on solving complex problems. If you enjoy digging into processes and making them better, we’d love to hear from you!

🌟 What You’ll Love About Working at Olly Olly

• Competitive Salary Based on Experience
• Flexible work: 100% remote, with core hours for seamless collaboration. 8:00 AM - 5:00 PM EST, Monday-Friday
• Work-life balance: Generous PTO, including 15 vacation days and U.S. holidays.
• Growth-oriented culture: Join an inclusive, international, and innovative team where your contributions make a tangible difference.

💡 Why Choose Us?

Join us during this pivotal transition as we transform from an agency to a human-centric SaaS provider. Your ideas, strategies, and solutions will directly impact the success of small businesses and our own growth!

Let’s shape the future of small business growth together! Apply now to join a team that’s as committed as they are supportive of each other.

🌈 Diversity and Inclusion at Olly Olly

At Olly Olly, we celebrate differences in background, culture, abilities, and perspectives because diversity drives innovation and creativity. Your voice matters here; it really does! And your unique perspective will help us shape the future of small business growth.