Billing & AR Specialist – B2B Subscriptions

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.

Our Vision

We're building the all-in-one platform for small business growth—streamlining operations so owners can manage their business more efficiently.

Our roots are in agency work, where we've already supported thousands of clients. Today, we're evolving into a SaaS-first company, pairing proven expertise with AI and automation to deliver affordable, results-driven solutions for small business owners.

Why We Need You

We're looking for a Billing & A/R Specialist- B2B Subscriptions who thrives in subscription-based billing environments. This isn't bookkeeping or payroll — it's a hands-on AR execution role where Stripe Subscriptions, reconciliations, disputes, and month-end reporting are at the core.

You'll take ownership of our end-to-end billing operations: managing subscription lifecycles, reconciling accounts, preparing evidence for disputes, and ensuring billing workflows run cleanly across systems like HubSpot. Your main impact will come from protecting revenue and keeping AR processes accurate and scalable.

The Impact You'll Have

• Manage the subscription lifecycle: plan changes, proration, cancellations, reconciliations, and revenue tracking.
• Own dispute representation: prepare and submit evidence packets to banks/payment processors to protect company revenue.
• Work across modern payment processors — Stripe strongly preferred, but experience with Adyen, WorldPay/FIS, Chase Paymentech, Braintree, CyberSource, First Data/Fiserv, PayU, Mollie, or similar is highly valuable.
• Maintain billing workflows in HubSpot, ensuring automation, data accuracy, and clean cross-team communication.
• Support month-end close: reconciliations, AR aging reports, and revenue reporting.
• Identify and implement process improvements to strengthen dunning workflows, dispute outcomes, and reconciliation accuracy.

What We Really Need From You

• 3+ years of hands-on billing and accounts receivable experience in a SaaS or subscription-based business.
• Proven expertise with subscription billing models (recurring revenue, proration, cancellations, renewals).
• Direct experience with dispute/chargeback management — you know what evidence wins.
• Experience working inside payment processors (Stripe, Adyen, WorldPay, Braintree, etc.).
• Prior exposure to U.S.-based SaaS or B2B billing environments.
• Strong knowledge of HubSpot for AR/billing workflows.
• Advanced Excel/Google Sheets skills for reconciliations, reporting, and AR analysis.
• Track record of building or optimizing dunning workflows to improve recovery rates.
• Detail-oriented, proactive, and comfortable owning critical AR processes in a fast-paced, high-growth environment.

What You'll Love About Working at Olly Olly

• Competitive salary based on experience.
• 100% remote role with core hours of 8:00 AM – 5:00 PM ET (Mon–Fri).
• Generous PTO: 15 vacation days + US holidays.
• Growth-oriented culture: join an inclusive, international, 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

Diversity & 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.