Olly Olly

Senior Billing Specialist, Stripe/Subscriptions

Olly Olly

full-time

Posted on:

Origin:  • 🇺🇸 United States

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Job Level

Senior

About the role

  • 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

Requirements

  • 3+ years of hands-on billing and accounts receivable experience in a SaaS or subscription business
  • Proven expertise with Stripe Subscriptions
  • 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)
  • 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
  • Given that this position requires English proficiency, we are only considering CVs provided in English