Remote Reconciliation & Payments Specialist (AI-Enhanced)

Overview

This is a hands-on, Remote Reconciliation & Payments Specialist role within the Billing & Collections team. Payments come in across multiple channels from customers ranging from small SMB merchants to large Enterprise accounts. The position ensures every payment is matched to what the customer was actually invoiced and stays on track until each item is genuinely resolved.

The work is detailed and largely spreadsheet-based (Excel). You’ll investigate unmatched, partial, or unexpected items to determine root cause, including following up on open items after month-end.

The role reports to the Billing & Collections Manager and works across several systems where data may be incomplete, inconsistent, or incorrect. You’ll also collaborate with cross-functional teams (Billing, Finance, Operations, and Customer Success) and communicate clearly with both internal stakeholders and customers when needed.

Responsibilities

• Reconcile customer payments against invoices across the full customer base (SMB to Enterprise).
• Match incoming payments to what the customer was actually invoiced and close the loop between payment received and invoice issued.
• Investigate every unmatched, partial, or unexpected item down to root cause; keep items from remaining unresolved.
• Track what each customer owes, confirm payment status, and follow up until fully resolved, including items that carry past month-end.
• Own accounts end to end by ensuring reconciliation work is clean, correct, and complete—not just started.
• Maintain clear, well-documented working papers showing how each balance was reached.
• Perform spreadsheet-based reconciliation work in Excel (pivot tables, lookups, and large data sets).
• Pull and cross-check data across multiple systems where data is often broken, incomplete, or inconsistent.
• Verify data critically—assume numbers may need confirmation and investigate discrepancies when values don’t match.
• Respond to requests from Billing, Finance, Operations, and Customer Success.
• Use day-to-day communication tools including Slack, monday.com, and email.
• When the fastest path to resolution, join customer calls to walk through reconciliation details.
• Explain billing and reconciliation situations clearly to non-finance stakeholders and customers.
• Identify manual, repetitive steps that can be improved and contribute to making reconciliation workflows smarter over time.
• Partner with AI tools (including Claude) to reduce manual effort as the role evolves; no prior automation experience required.

Requirements

• 2+ years of experience in reconciliation, collections, billing, or accounts receivable (ideally in fintech, SaaS, or eCommerce).
• Ownership mindset: take responsibility for accounts, work down into details, and ensure resolution before considering items complete.
• Persistence: stay on unpaid or unreconciled items until closed, including well after month-end.
• Strong Excel skills, including pivot tables, VLOOKUP/XLOOKUP, SUMIFS, and working with large data sets.
• Critical eye for data: comfortable working across multiple systems with broken or inconsistent data and instinctively verifying rather than assuming.
• Strong attention to detail and the ability to reconcile discrepancies to zero.
• Responsive and easy to work with; comfortable handling requests across Slack, monday.com, email, and occasional customer calls.
• Clear communicator able to explain reconciliation or billing issues simply to people who aren’t in finance (including customers).
• Interest in using AI tools (including Claude) to reduce manual effort over time; prior automation experience is not required.
• Native or near-native English with clear, professional written and verbal communication.
• Comfortable working with customers of all sizes, from SMB to Enterprise.

Preferred Qualifications

• Familiarity with chargebacks, payment disputes, or PSP data.

Compensation & Benefits

• Full-time, Remote position.

Location

• Remote