Remote Reconciliation & Payments Specialist (AI-Enhanced)

Chargeflow

1d•Remote

About The Position

Chargeflow is hiring a full-time remote Reconciliation & Payments Specialist for its Billing & Collections team. The role owns reconciliation and collections across customers ranging from SMB merchants to Enterprise accounts, ensuring incoming payments are matched to invoices and that outstanding balances are followed through to resolution, including after month-end. The work is spreadsheet-intensive and involves investigating unmatched, partial, or unexpected items across multiple systems, where data may be incomplete, inconsistent, or incorrect. The specialist maintains clear working papers and is accountable for accurate, complete reconciliations. The position collaborates with Billing, Finance, Operations, and Customer Success, using Slack, monday.com, and email, and may involve calls with customers to explain billing or reconciliation issues in clear, accessible language. Over time, the specialist is expected to identify repetitive manual work and use Claude and other AI tools to make workflows more efficient; prior automation experience is not required. The role reports to the Billing & Collections Manager.

Requirements

At least 2 years of experience in reconciliation, collections, billing, or accounts receivable.
Strong Excel skills, including pivot tables, VLOOKUP/XLOOKUP, SUMIFS, and working with large datasets.
A strong ownership mindset and willingness to take responsibility for accounts and follow issues through to resolution.
Persistence in following up on unpaid or unreconciled items, including beyond month-end.
Ability to critically assess and verify data across multiple systems, including when data is broken, incomplete, or inconsistent.
Strong attention to detail and ability to investigate discrepancies until balances reconcile.
Responsiveness and ability to work across Slack, monday.com, email, and occasional customer calls.
Clear written and verbal communication, including explaining billing or reconciliation issues to non-finance colleagues and customers.
Interest in using AI tools, including Claude, to reduce manual effort; prior automation experience is not required.
Native or near-native English proficiency with clear, professional written and verbal communication.
Comfort working with customers of all sizes, from SMB to Enterprise.

Nice To Haves

Experience in fintech, SaaS, or eCommerce.
Familiarity with chargebacks, payment disputes, or PSP data.

Responsibilities

Reconcile customer payments against invoices across SMB and Enterprise accounts.
Match each incoming payment to the amount invoiced and close the loop between payments received and invoices issued.
Investigate unmatched, partial, or unexpected transactions to determine root causes and resolve discrepancies.
Track customer debts and follow up until payment and reconciliation issues are fully resolved, including items that remain open after month-end.
Own accounts end to end and ensure reconciliations are clean, correct, and complete.
Maintain clear, well-documented working papers showing how balances were calculated.
Use Excel to process and analyze large datasets, and pull and cross-check information across multiple systems.
Verify data rather than assume it is correct, and investigate conflicting figures until they are resolved.
Respond to requests from Billing, Finance, Operations, and Customer Success through Slack, monday.com, and email.
Speak with customers when useful to resolve reconciliation matters and explain billing issues in plain language.
Identify repetitive manual tasks and use Claude and other AI tools over time to improve workflows and reduce manual effort.