Reconciliation & Payments Specialist

Who We're Looking For - The Dream Maker

This is a hands-on reconciliation role inside Chargeflow's Billing & Collections team. Money comes in from customers of every size — from small SMB merchants to large Enterprise accounts — across multiple payment channels, and you are the person who makes sure every payment is matched against what the customer was actually invoiced. It's detailed work, it lives largely in Excel, and getting it right matters.

The core of the job is ownership: you reconcile what a customer owes against what they've paid, you close the loop against the invoice we issued, and you don't let it go until it's genuinely resolved — including chasing an open item well after the month has closed. "It'll probably sort itself out" is not part of the role. If a customer hasn't paid their debt, you stay on it until they have.

You'll work across several systems where the data is often broken, incomplete, or simply wrong — so a critical eye is not optional. You need to be the person who notices that two numbers don't agree and cares enough to find out why. It can be frustrating, but the payoff is real: there's genuine satisfaction in untangling a mess and getting it to tie out.

We're also a company that wants to do this smarter over time. You won't be expected to build automation from day one — but we do want someone who is hungry to turn manual, repetitive work into AI-assisted workflows, with Claude as your day-to-day partner for getting there. The role sits within Billing & Collections and reports to the Billing & Collections Manager.

About Chargeflow

Chargeflow is a leading force in fintech innovation, tackling chargeback fraud and the impact it has on online businesses. Born from a deep passion for technology and eCommerce, we’ve developed an AI-driven solution that helps merchants manage credit card disputes, recover lost revenue, and protect their businesses through a unique success-based model.

Backed by $49M from Viola Growth, OpenView, Sequoia Capital, and other top-tier global investors, Chargeflow is on a product-led growth journey. We’re a tight-knit team of passionate builders and entrepreneurs, united by our mission to revolutionize eCommerce and protect online businesses from chargeback fraud.

What You’ll Own

Reconciliation & Collections

• Reconcile customer payments against invoices across the full customer base — from small SMB merchants to large Enterprise accounts.
• Match every incoming payment to what the customer was actually invoiced, and close the loop between the payment received and the invoice issued.
• Investigate every unmatched, partial, or unexpected item down to root cause — don't leave gaps open.
• Track what each customer owes, confirm the debt has actually been paid, and follow up until it's fully resolved — including items that carry past month-end.
• Own your accounts end to end: you're responsible for the reconciliation being clean, correct, and complete, not just started.
• Keep clear, well-documented working papers so anyone can see how a balance was reached.

Working Across the Systems

• Do the heavy lifting in Excel — this is a spreadsheet-intensive role (pivot tables, lookups, large data sets).
• Pull and cross-check data across several systems where the data is often broken, incomplete, or inconsistent.
• Keep a critical eye at all times — assume the data needs verifying, and dig in when two numbers don't agree.
• Take real ownership of the details: notice the discrepancy, care about it, and drive it to a clean answer.

Communication & Responsiveness

• Be responsive to the people who depend on you across the company — Billing, Finance, Operations, and Customer Success.
• Work fluidly across the channels the business runs on: Slack, monday.com, and email.
• When it's the fastest way to resolve something, get on a call with a customer and walk them through their reconciliation directly.
• Explain a billing or reconciliation situation in plain, clear language to someone who isn't in finance.

Making the Work Smarter (Over Time)

• Look for manual, repetitive steps that shouldn't stay manual — and bring the hunger to improve them.
• Partner with Claude and other AI tools day-to-day to speed up reconciliation and reduce manual effort as you grow into the role.

What You Bring

• 2+ years of experience in reconciliation, collections, billing, or accounts receivable — ideally in fintech, SaaS, or eCommerce - Must
• A genuine ownership mindset — you take responsibility for your accounts, go down into the detail, and don't consider something done until it's actually resolved - Must
• The persistence to stay on an unpaid or unreconciled item until it's closed, including well after month-end — you're not comfortable letting things sit - Must
• Strong Excel skills — this is a spreadsheet-heavy role (pivot tables, VLOOKUP/XLOOKUP, SUMIFS, large data sets) - Must
• A critical eye for data — comfortable working across multiple systems where the data is broken or inconsistent, and instinctively verifying rather than assuming - Must
• Strong attention to detail — able to spot when two numbers don't agree and to work a discrepancy down to zero - Must
• Responsive and easy to work with — comfortable fielding requests across Slack, monday.com, email, and the occasional customer call - Must
• Clear communicator — able to explain a reconciliation or billing issue simply to people who aren't in finance, including customers - Must
• Curious about doing the work smarter — interested in using AI tools (Claude included) to reduce manual effort over time. Prior automation experience is not required - Must
• Native or near-native English — clear, professional written and verbal communication - Must
• Comfortable working with customers of all sizes, from SMB to Enterprise - Must
• Familiarity with chargebacks, payment disputes, or PSP data — an advantage.

How We Work

We move quickly, collaborate across teams, and expect people to take ownership from problem to resolution. We build strong customer relationships through responsiveness, transparency, and measurable results.

This is a full-time, Remote position!

If you’re looking to take ownership of strategic enterprise relationships and directly influence customer retention and growth, we’d love to hear from you.