Billing Specialist

Sterlington, PLLC; Oregon; Hybrid; USD 55,000 - 85,000; Full time

Job summary

Sterlington PLLC is seeking a Billing Specialist to own invoicing and billing operations in a fast-paced, client-facing environment. You will ensure invoices are accurate, timely, and aligned with client expectations, collaborating with partners, finance, and client teams.

In this role, you will review time entries and expenses, resolve billing queries, and support month-end processes, while identifying process improvements and ensuring clean billing records. Remote-friendly environment.

Qualifications

• 4–7 years of billing, AR, or finance operations experience.
• Experience with AI-assisted billing and AI-augmented workflows.
• Strong attention to detail and ability to manage multiple invoices and deadlines.
• Experience with accounting or billing systems (ERP, legal billing tools) and advanced Excel.

Responsibilities

• Prepare, review, and issue invoices accurately and on time, including billable hours and client-specific terms.
• Collaborate with partners and internal stakeholders 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, organized billing records and documentation.
• Support month-end processes by ensuring billing data is complete and up to date.
• Identify recurring billing issues and propose practical process improvements.
• Partner with collections and accounts receivable to ensure smooth handoff from invoicing to payment.

Skills

Billing experience

AI-assisted billing

AI-augmented workflows

Automation of finance systems

Attention to detail

Handling multiple invoices

Communication

Organization

Excel skills

Data proficiency

Tools

ERP systems

Legal billing tools

Job description

Location: 100 % remoteContract: Full-time, Independent ContractorPosting Jurisdictions : To support US Eastern Time working hours

Our Firm:Sterlington PLLC is a full-service law firm focusing on complex corporate, litigation, executive compensation, and private wealth matters. As a firm, we focus on the economics as well as the legal aspects of our matters. Among other strengths, Sterlington is the ultimate law firm for founders, senior executives, and UHNWIs as well as their related businesses.

Learn more at: The Opportunity

We're looking for a Billing Specialist to take ownership of invoicing and billing operations in a fast-paced, client-facing environment. This role sits at the center of revenue operations, working closely with partners, finance, and client teams to ensure invoices are accurate, timely, and aligned with client expectations. You'll play a key role in keeping billing clean, reducing friction with clients, and supporting overall cash flow.

What You’ll Do:

• Prepare, review, and issue invoices accurately and on time, including billable hours and client-specific billing arrangements
• Work closely with partners and internal stakeholders to validate billing details before sending invoices
• Track billing schedules and ensure deadlines are consistently met
• Review time entries, expenses, and billing data to ensure accuracy and compliance
• Resolve billing queries and disputes by coordinating with internal teams and communicating with 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

What We’re Looking For :

• 4-7 years of experience in billing, accounts receivable, or finance operations
• Familiarity with AI-assisted billing tools: comfortable using AI features in accounting or ERP platforms to flag anomalies, automate invoice matching, or surface overdue accounts faster
• Open to AI-augmented workflows: willing to adopt AI tools that streamline repetitive tasks like data entry, payment follow-ups, or reconciliation, freeing up time for higher-value problem-solving
• Experience automating finance systems
• Strong attention to detail; you catch errors before they become problems
• Comfortable working with different billing structures (hourly, fixed fee, retainers)
• Clear communicator, able to follow up, clarify, and resolve issues quickly
• Organized and able to manage multiple invoices and deadlines at once
• Experience with accounting or billing systems (ERP, legal billing tools, etc.)
• Solid Excel skills and confidence working with data

At Sterlington, we believe that world-class talent has no boundaries. We are committed to fostering a diverse and inclusive environment where unique perspectives are valued and every individual has the opportunity to thrive.