Billing Specialist

Location: Remote (EST or CST)
Schedule: Part-time (20-25 hrs/week)
Please note: this is a contractor role through December 2026.

About the role

The Billing Contractor supports recurring billing operations across the organization, with a primary focus on accounts receivable, collections follow-up, subscription billing administration, and related invoicing tasks. This role works closely with the Billing & Special Projects Manager and partners with Account Managers and Support to keep client billing accurate, timely, and organized. The ideal candidate is highly organized, comfortable communicating directly with clients about payment matters, and able to learn and work across multiple software systems.

Responsibilities

• Monitor customer accounts and follow up on outstanding, overdue, failed, or reversed payments.
• Communicate professionally with clients regarding balances owed, payment issues, and existing payment plans.
• Maintain consistent payment-plan follow-up and document outreach, actions taken, and next steps.
• Administer recurring and subscription billing for assigned client segments, including basic invoice and customer updates.
• Support ad hoc invoicing and billing requests as they arise.
• Review billing information for accuracy, identify discrepancies, and escalate issues when appropriate.
• Partner with the Support team on billing-related escalations and coordinate with internal stakeholders to resolve client issues.
• Provide clear day-to-day status updates on completed work, open items, and follow-up needs.
• Handle customer billing information and financial workflows with discretion and care.

Requirements

• Experience in billing, collections, or accounts receivable; direct AR experience is strongly preferred.
• Strong organization and attention to detail, with the ability to track multiple accounts and follow-ups without losing momentum.
• Clear, professional written and verbal communication skills, including comfort communicating directly with clients about payment issues.
• Technology-forward and comfortable learning multiple software applications and switching between systems throughout the day.
• Ability to work independently in a remote environment while maintaining consistent communication with the manager and team.
• Sound judgment and trustworthiness when working with billing systems and potentially sensitive customer information.

Preferred Experience

• Hands-on experience with Stripe or another online payment/billing platform.
• Experience with Sage Intacct or a comparable accounting/ERP system.
• Familiarity with monday.com, Outlook, ShulCloud, or similar business applications is helpful but not required.
• Experience supporting subscription or recurring-revenue billing environments.

Benefits

• Medical, dental, and vision insurance options
• 100% Employer paid short/long term disability
• 100% employer-paid Basic Life and AD&D insurance
• 401(k) retirement plan with a 100% company match up to 4%
• Flexible paid personal/vacation time built on mutual trust and accountability
• 10 sick days annually
• 10 company paid holidays
• 12 weeks paid parental leave

Pay

$25/hr