Remote Billing Operations Leader

Scale to Win, Inc; United States; Remote; USD 72,000 - 88,000; Full time

Benefits offered by this job

401k matching

Paid holidays

Paid vacation 24 days

Parental leave

Medical insurance

Remote work stipend

Text donation program

Professional development stipend

Job summary

Scale to Win, Inc. is seeking a Manager of Billing Operations to oversee daily billing, invoicing, and accounts receivable in a fully remote environment.

You will ensure billing accuracy and timeliness while coordinating with CX, Sales, and Accounting to resolve issues. The role emphasizes hands-on collections, process improvements, regulatory compliance across states, and close collaboration to improve cash flow.

Qualifications

• 3+ years of experience in billing operations, accounts receivable, or corporate collections.
• Strong communication skills with direct customer outreach (phone and email) for collections.
• Demonstrated ability to collaborate across teams (Sales, CX, Accounting) to resolve billing challenges.
• Systems-thinking mindset to streamline workflows and fix repetitive errors.
• Familiarity with GAAP related to A/R and bad debt is a plus.

Responsibilities

• Monitor end-to-end billing workflows for recurring and usage-based products.
• Generate weekly, one-off, ad-hoc, and manual invoices as needed.
• Monitor billing controls for accuracy in invoice generation, proration, and usage calculations.
• Oversee A/R aging reports and cash application activities to ensure timely posting of payments.
• Drive collections through direct outreach including calls and emails to recover overdue funds.
• Negotiate payment plans with late-paying customers while preserving relationships.
• Partner with Sales and CX to align on collections and reduce escalations.
• Support root-cause billing improvements and contract structuring considerations.
• Assist with multi-state regulatory filings and tax obligations with CorpNet.

Skills

Billing operations

A/R collections

Customer outreach

Cross-functional collaboration

GAAP familiarity

Job description

Scale to Win, Inc. is seeking a Manager of Billing Operations to oversee daily billing, invoicing, and accounts receivable in a fully remote environment.

You will ensure billing accuracy and timeliness while coordinating with CX, Sales, and Accounting to resolve issues. The role emphasizes hands-on collections, process improvements, regulatory compliance across states, and close collaboration to improve cash flow.