Billing Specialist

Location: Remote (EST or CST)

Schedule: Part-time (20-25 hrs/week)

**Please note: this is a contractor role through December 2026.**

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.

• 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.

• 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.

• 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.

The Company offers a comprehensive employee benefits program, including:

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

Salary Range Disclosure

The base range represents the low and high end of the Togetherwork salary range for this position. Actual salaries will vary and may be above or below the range based on factors including, but not limited to location, experience, and performance. The range listed is just one component of Togetherwork's total compensation package for employees. Other rewards may include discretionary bonuses, long term incentives, a flexible paid vacation/personal time policy, 6 weeks paid parental leave and more.

Salary Range

$25/hr

Inclusion and Diversity: Togetherwork is an Equal Employment Opportunity Employer. We are a company where diverse backgrounds, experiences and viewpoints are valued. Togetherwork does not make hiring or employment decisions on the basis of race, color, religion, gender, gender identity, sex, sexual orientation, disability, veteran status, age, ethnic or national origin, or any other basis protected by all local, state or federal laws.

Interview Process & Expectations
Our interviews are designed to be interactive and conversational. Candidates are expected to respond based on their own experience and thinking during live interviews.

To ensure a fair and consistent interview experience, the use of real-time AI tools or other external assistance to generate or guide interview responses is not permitted. Interviews are intended to reflect an individual's judgment, problem-solving approach, and communication.