Remote Billing Specialist: AI-Driven Invoicing & Cash Flow

Sterlington, PLLC; Santiago; Remote; CLP 58,939,000 - 88,409,000; Full time

Job summary

Sterlington PLLC, a full-service law firm, seeks a Billing Specialist to own invoicing and billing operations in a fast-paced, client-facing environment. This role sits at the center of revenue operations, partnering with partners, finance, and client teams to ensure invoices are accurate, timely, and aligned with client expectations.

You’ll help keep billing clean, reduce client friction, and support overall cash flow while working in a remote, independent contractor capacity with US Eastern

Qualifications

• 2–5+ years of experience in billing, accounts receivable, or finance operations.
• Familiarity with AI-assisted billing tools in accounting or ERP platforms.
• Open to AI-augmented workflows to streamline repetitive tasks like data entry or follow-ups.
• Strong attention to detail and ability to catch errors before they become problems.
• Experience with multiple billing structures (hourly, fixed fee, retainers).
• Solid Excel skills and comfort working with data.
• Clear communication and ability to follow up quickly.

Responsibilities

• Prepare, review, and issue invoices accurately and on time, including billable hours and client-specific billing arrangements.
• Collaborate with partners and internal teams to validate billing details before sending invoices.
• Track billing schedules and ensure deadlines are met consistently.
• Review time entries, expenses, and billing data for accuracy and compliance.
• Resolve billing queries and disputes by coordinating with internal teams and clients.
• Maintain clean and organized billing records and documentation.
• Support month-end processes by ensuring billing data is complete and up-to-date.
• Identify recurring billing issues and suggest practical improvements to processes.
• Partner with collections and AR to ensure smooth handoff from invoicing to payment.

Skills

Attention to detail

Clear communicator

Organized

Deadline-oriented

Tools

ERP systems

Excel

Legal billing tools

AI-assisted billing tools

Job description

Sterlington PLLC, a full-service law firm, seeks a Billing Specialist to own invoicing and billing operations in a fast-paced, client-facing environment. This role sits at the center of revenue operations, partnering with partners, finance, and client teams to ensure invoices are accurate, timely, and aligned with client expectations.

You’ll help keep billing clean, reduce client friction, and support overall cash flow while working in a remote, independent contractor capacity with US Eastern