Order to Cash Specialist

Order to Cash Specialist

Location: Remote

Team: Finance

Reports to: Head of Global Accounts Receivable (AR) and Head of Financial Operations

�� The Role

We are looking for an exceptional Order to Cash Specialist to join our high-performing global finance team. This is not a junior or learning role — we are only considering candidates with a proven track record and deep expertise in payment reconciliation, particularly with Stripe.

You will take full ownership of the daily reconciliation of incoming and outgoing transfers across our global payment infrastructure. Your work will be mission-critical to ensuring the integrity of our cash flow, accurate owner payouts, and operational scalability. You will be expected to spot and resolve payment flow issues before they impact our partners and to drive automation and continuous improvement across all O2C processes.

This role is designed for someone who is deeply analytical, highly detail-oriented, and passionate about leveraging technology to solve complex problems in a fast-paced transactional environment.

�� Key Responsibilities

• Take full ownership of the reconciliation of all incoming and outgoing transfers within Stripe and other payment systems
• Detect and resolve misconfigurations, miscalculations, and discrepancies across complex payment flows
• Analyze payout processes, identify bottlenecks, and implement improvements to ensure timely and accurate disbursements to property owners and vendors
• Lead the end-to-end transactional Order to Cash cycle including invoicing, collections, payment application, and GL postings
• Reconcile OTA platform payments (e.g., Booking.com, Airbnb) with a focus on platform fee and commission accuracy
• Use SQL and data tools to extract, validate, and reconcile financial and transactional data
• Drive adoption of AI and automation tools to streamline reconciliation, reduce errors, and increase scalability
• Contribute to a clean month-end close process by delivering reconciled AR and revenue data
• Maintain strong internal controls and detailed documentation to ensure audit readiness and process transparency

�� What We're Looking For

• Minimum 4 years of specialist experience in transactional finance or payment reconciliation, ideally with Stripe or other large-scale PSPs
• Demonstrated ability to troubleshoot complex payment flow issues and proactively implement lasting solutions
• Advanced SQL and data analysis skills — you must be comfortable working with structured financial data
• Deep knowledge of the full Order to Cash cycle and GL accounting practices
• Prior experience reconciling large volumes of transactions from OTA platforms such as Airbnb or Booking.com
• Strong Excel/Google Sheets proficiency (complex formulas, pivot tables, lookups)
• Comfortable working in a fast-paced, high-volume, and cross-functional environment
• Fluent in English (Portuguese or another European language is a plus)