Senior Finance Operations Specialist – Accounts Receivable & Collections

The Pineapple Agency is looking for a Senior Finance Operations Specialist - Accounts Receivable & Collections to take ownership of a critical part of our Finance organization.

This is not a traditional transactional AR role.

We are looking for someone who can step into a growing, fast-moving business, take ownership of our accounts receivable and collections process, identify where things are breaking down, and build the structure needed to improve how cash moves through the organization.

You will own the day-to-day execution of AR and collections while helping us build a more scalable invoice-to-cash and working capital process as the company grows.

If you enjoy bringing structure to ambiguity, solving problems at their root cause, working directly with customers and internal teams, and improving the process rather than simply operating within it, this role may be a strong fit.

You will be responsible for managing and improving the end-to-end AR and collections process, including customer balances, payment commitments, billing issues, cash visibility, and process improvement.

• Own the AR aging and actively manage outstanding customer balances
• Establish and maintain a disciplined collections cadence
• Communicate directly with customers regarding invoices, payment status, disputes, and commitments
• Track promises-to-pay and proactively follow through on missed commitments
• Partner with Project Management, Account Management, and Finance to resolve billing issues and remove barriers to collection
• Identify root causes behind delayed payment, including missing documentation, purchase orders, billing errors, project closeout issues, credits, and disputes
• Support invoice accuracy, cash application, account reconciliations, and resolution of unapplied or short-paid balances
• Build and maintain a weekly forecast of expected customer receipts
• Monitor AR aging, DSO, overdue balances, and other working-capital metrics
• Develop standard work, reporting, and processes that make AR more predictable and scalable
• Identify opportunities to improve the broader invoice-to-cash process
• Support additional Finance Operations and cross-functional business priorities as the organization evolves

Within your first several months, we expect you to develop a strong understanding of our customer portfolio, establish clear visibility into outstanding receivables, and create a consistent collections rhythm.

Over time, success means:

• Reduction in AR aging balances
• More reliable customer payment commitments, and cash conversion cycle process.
• Better visibility into expected cash receipts
• Faster identification and resolution of billing issues

We're looking for someone with approximately 3+ years of experience in B2B accounts receivable, commercial collections, or Finance Operations
, with meaningful direct responsibility for customer collections.

Strong candidates will have experience with:

• Managing AR aging and commercial collections
• Communicating directly with business customers regarding overdue balances
• Resolving disputes, billing discrepancies, and payment issues
• Working with accounting or ERP systems
• Excel and financial reporting
• Building or improving processes rather than simply following established procedures
• Managing multiple priorities independently in a fast-moving environment

• Experience in project-based services, fabrication, construction, events, agencies, professional services, or milestone-based billing environments is helpful but not required.

The ideal candidate :

• Take ownership without waiting to be told every next step
• Are comfortable walking into processes that are still being built
• Ask "why?" when something repeatedly breaks
• Can be persistent with customers without damaging the relationship
• Communicate clearly and professionally across different teams
• Know when to solve a problem yourself and when to escalation it
• Are organized enough to manage dozens of open items without losing accountability
• Enjoy turning…