[Hiring] AR & Billing Specialist @Darkroom

Role Description

Darkroom is hiring an AR & Billing Specialist to join the Finance team. You’ll own billing, collections, accounts payable, creator payments, and cash visibility across more than 80 client accounts and around 100 invoices a month. You’ll report to the SVP of Finance and work closely with the Finance Operations Manager, who sets our collections strategy, as well as our account leads and external bookkeeper.

This is not a reminder-sending role. We want someone who knows every account, spots payment risk early, and decides how to approach each client so we get paid on time without damaging the relationship.

This role is built for someone who sees AI as a core part of how finance gets done. You’ll use tools like Claude to check calculations, automate repetitive billing and follow-up work, and build workflows that raise both the speed and accuracy of our output.

This is a fully remote role supporting a team in the EST time zone (9 AM–5 PM EST).

What You’ll Do

• Prepare and issue all client invoices each cycle, including recurring retainers, one-off projects, variable and performance fees, and hourly web-support work.
• Reconcile tracked hours and variable-fee calculations against contracts and scopes before invoices go out.
• Keep the billing schedule current as clients start, change scope, pause, or offboard.
• Own collections execution end to end: run the follow-up calendar, manage AR aging and days sales outstanding, and follow the collections strategy set for each account.
• Carry out the approach set for each account, such as one consolidated reminder before the due date, a call with the client’s finance team, or bringing in the account lead, and recommend changes when an approach isn’t working.
• Join the daily cash flow check-in led by the Finance Operations Manager.
• Flag at-risk accounts early, such as slipping payment patterns, disputes, or unresponsive contacts, with a recommended action.
• Prepare the weekly cash and AR report, and draft the cash and collections section of the monthly report.
• Keep the weekly cash forecast current, with expected receipts by client and by week.
• Run accounts payable in Ramp: enter vendor bills, check them against approvals and contracts, schedule payments, and keep vendor records current.
• Pay creators, partners, and referral payouts in Ramp once amounts are approved, and keep payee records current.
• Record invoices and payments in QuickBooks, working alongside our external bookkeeper.
• Peer-check teammates’ work, such as reported MRR and client data against billing records.
• Maintain and improve our collections playbook and billing processes.

Qualifications

• You have 2–4 years of experience in accounts receivable, accounts payable, billing, or collections, ideally at an agency, professional services, or SaaS company with US clients.
• You have hands-on experience with QuickBooks Online. Experience with Ramp or a similar AP tool is a plus.
• You’re strong in Google Sheets or Excel, including lookups, pivot tables, and reconciliations.
• You have a high bar for accuracy. Invoices you send are right the first time.
• You’re a confident communicator, polite but firm with US client contacts, by email and on calls.
• You have good judgment about people and priorities. You know when to push, when to escalate, and when to wait.
• You take initiative. You raise problems together with a proposed fix instead of waiting to be told.
• You use Claude or similar AI tools in your work, or you’re eager to.
• You’re fluent in written and spoken English.

Benefits

• Unlimited PTO + local holidays (relevant to your hub): Rebooting is part of the work. Take the time you need to stay sharp.
• Remote-First Culture: Many roles are fully remote. Employees based in or near our New York or Lisbon HQs are expected to work hybrid with weekly in-office time. Hub locations include Brazil and Spain.
• Parental Leave: Flexible parental leave to support new parents during this important transition.
• Growth: Our interdisciplinary model gives every Darkroomer exposure far beyond their core role. Grow your skills, expand your influence, and stay at the forefront of the industry.

Equal Opportunity Statement

Darkroom is an equal opportunity workplace. We are dedicated to equal employment opportunities regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, or Veteran status. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements.