Collections Specialist

Senior Collections Specialist

San José, Costa Rica

Position Title: Senior Collections Specialist

Contract: Full-time, Independent Contractor

Posting 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 economic 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.

The Opportunity

This role is a great fit for someone who enjoys owning the collections process and making a direct impact on cash flow. As a Collections Specialist, you'll be the primary point of contact for customers on outstanding balances, working proactively and professionally to resolve issues and secure timely payments. You'll partner closely with internal teams to address billing questions, keep accounts accurate, and improve collections processes over time. It's a hands-on, visible role where persistence, communication, and attention to detail truly matter.

What You'll Do:

• Own collections end-to-end for assigned client accounts, following up on overdue invoices by phone and email
• Make outbound collections calls (this is not an email-only role) and handle payment conversations professionally
• Negotiate payment plans when needed and document commitments with clear follow-up
• Monitor AR aging and proactively flag collection risks before balances escalate
• Resolve billing questions and disputes by working closely with billing, accounting, sales, and client services
• Apply and reconcile payments, credits, and adjustments accurately
• Maintain clear, well-organized records of all collection activity and client communications
• Support month-end close by keeping AR balances accurate and up to date
• Take full ownership of the AR aging report, updating and analyzing it weekly
• Produce and share a weekly collections priority list for the team
• Track payment promises and flag broken commitments for escalation
• Prepare weekly collections updates that feed directly into cash-flow forecasting
• Analyze client payment behavior (days-to-pay, trends, early warning signals)
• Monitor AR concentration risk across clients and partner books
• Prepare data-backed write-off and reserve recommendations
• Serve as the main point of contact for partner-level collections escalations, following firm guidelines
• Own and maintain the Collections Playbook and suggest improvements over time
• Provide feedback to billing on recurring invoice issues and rejection patterns
• Track client retainer balances and flag low retainers ahead of billing cycles
• Validate payment application by cross-checking bank activity, aging, and client confirmations

What We're Looking For:

• 5+ years of experience in collections, accounts receivable, or a related finance role
• Strong communication skills (English C2 or near-native/native) and the ability to handle difficult payment conversations professionally
• Detail-oriented, organized, and comfortable managing multiple accounts at once
• Solid understanding of AR processes, invoicing, and payment applications
• Experience using accounting or ERP systems
• Proficiency in Excel and basic financial reporting
• Reliable, persistent, and accountable—someone who follows through and gets results
• Comfortable using AI-enabled tools, automation, or technology to improve collections workflows, reporting accuracy, and follow-up efficiency

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. We encourage all qualified candidates to apply.