Senior Billing Specialist

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 Senior Billing (Stripe/Subscriptions) Specialist 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, preparing evidence for disputes, reconciling accounts, and supporting financial reporting. Collections outreach is part of the job, but your main impact will come from protecting revenue and running clean AR processes at scale.

The Impact You'll Have

• Manage the subscription lifecycle in Stripe: new setups, plan changes, proration, cancellations, reconciliations, and revenue tracking.
• Own dispute representment: prepare and submit evidence packets to banks/card networks to protect company revenue.
• Execute and maintain billing workflows in HubSpot, including automation of tickets and cross-team communication.
• Support month-end close: AR aging reports, reconciliations, and cash collection forecasting.
• Investigate delinquencies: analyze root cause, adjust accounts, and handle outbound collections calls/emails when needed.
• Partner with Sales & Customer Success to ensure accurate subscription data.
• Identify and implement process improvements to make AR more efficient and scalable.

What We Really Need From You

• 3+ years of hands-on billing and accounts receivable experience in a SaaS or subscription business.
• Proven expertise with Stripe Subscriptions (not just invoice/payment processing).
• Direct experience preparing and submitting dispute representment evidence to banks/payment processors.
• Strong knowledge of HubSpot for AR/billing workflows.
• Familiarity with collections outreach (calls + email), but with a bias toward solving the process and data issues behind delinquency.
• Advanced Excel/Google Sheets skills for reconciliations, AR aging, and reporting.
• Detail-oriented, proactive, and comfortable owning critical AR processes in a fast-paced, high-growth environment.

Big Pluses

• Prior exposure to US-based SaaS subscription billing.
• Track record of building or optimizing dunning workflows.

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.