Olly Olly

Billing Specialist

• 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

Senior Billing Specialist, Stripe/Subscriptions

QA Engineer

• Analyze team performance and project data to identify opportunities for improving delivery speed, quality, and efficiency.
• Work closely with the SEO and Digital Marketing Director to enhance workflows, launch new initiatives, and ensure website production supports overall marketing strategy.
• Partner with leadership to spot risks, remove roadblocks, and keep projects on schedule.
• Review and refine the output of the QA, design, and web support teams to ensure error-free, on-brand client websites and digital assets.
• Lead, coach, and develop your team of 10, setting clear expectations, managing workloads, and fostering accountability.
• Collaborate cross-functionally with SEO, digital marketing, and client-facing teams to ensure client deliverables align with business needs and drive measurable results.
• Actively contribute to Olly Olly’s culture by providing regular feedback, sharing best practices, and promoting continuous improvement.
• Identify workflow bottlenecks and standardize processes to ensure smooth project delivery and high-quality client outcomes.

Digital Operations Manager, Web, QA and Design

Full-stack Engineer

• Work with Flutter/Dart to build a multi-platform product that impacts small business owners daily
• Develop, design, and maintain scalable web and mobile applications
• Write clean, efficient, well-documented, maintainable code
• Collaborate with cross-functional teams to design, develop, test, and deploy code
• Troubleshoot and debug production issues
• Contribute across the full software development lifecycle from planning and architectural design to production and deployment
• Support and implement new features to expand the value of the Olly Olly App in the market

Junior Software Engineer

Operations

• 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.

Senior Billing Specialist, Stripe/Subscriptions

Digital Operations Manager, Web, QA and Design

Junior Software Engineer

Billing and Accounts Receivable Operations Specialist