Billing, AR & Collections Lead

Key Responsibilities

Billing, AR & Collections - SMB (High Volume)

• Own end-to-end billing and invoicing for a high-volume book of SMB dental practice customers, including recurring subscription billing and usage-based charges.

• Oversee the end-to-end collections process, ensuring efficient workflows, timely follow-up, accurate account resolution, and consistent execution of billing and collection procedures.

• Monitor AR aging across the SMB book, flag risk accounts early, and drive down days sales outstanding (DSO) and delinquency rates.

• Partner with Customer Success and Support to resolve billing disputes and payment failures quickly, minimizing involuntary churn caused by billing friction.

• Own accurate execution of SMB promotions and discounting (free months, introductory pricing, retention offers) in the billing system, so what Sales/CS grants is what actually shows up on the invoice.

Billing, AR & Collections - Enterprise / DSO

• Own billing and collections for Enterprise and DSO accounts, including complex, contract-driven invoicing (multi-location rollups, tiered pricing, custom terms, milestone or usage-based fees).

• Manage a smaller number of high-dollar, high-touch relationships, working directly with customer finance and procurement contacts to resolve disputes and negotiate payment plans where needed.

• Partner with Legal and Sales on contract terms that affect billing and collectability (payment terms, invoicing triggers, true-ups, nonrefundable fee language) before deals close.

• Serve as the point of escalation for at-risk Enterprise receivables, including past-due balances tied to contractual disputes.

Build the Function

• Design and implement the systems, policies, and controls Pearl needs as it scales toward $100M+ ARR - this is a build role, not a maintain role.

• Evaluate and implement billing/AR tooling and automation (in partnership with RevOps and Data) to reduce manual work and support both high-volume SMB and complex Enterprise billing in one coherent system.

• Establish credit policies, write-off and bad debt procedures, and revenue recognition-adjacent controls in partnership with the Controller.

• Build the billing/AR reporting Pearl does not yet have: aging, DSO, cash forecasting inputs, and collections effectiveness, for use in board and leadership reporting.

• Partner with Sales and Customer Success to ensure pricing and sales initiatives - discounts, free months, promotional terms, contract concessions - are implemented correctly and consistently in billing systems, so what was sold matches what is invoiced.

• Manage and grow the Billing/AR team, starting with one direct report today and scaling headcount as volume and complexity require.

Build with AI

• Bring an AI-forward mindset to a function that is still largely manual across the industry: identify where AI and automation can replace manual dunning, reconciliation, and dispute triage work.

• Use AI tools to accelerate collections outreach, aging analysis, and reporting rather than defaulting to spreadsheets and manual follow-up.

• Partner with RevOps and Data to pilot AI-enabled billing and collections workflows, such as automated dispute categorization or payment risk scoring, as Pearl scales.

Qualifications

• 5+ years in billing, accounts receivable, or collections, including meaningful time in a startup or other fast-paced, high-growth environment.

• Direct experience building AR/billing processes and systems from scratch, not just operating an inherited function.

• Experience managing both high-volume, low-touch billing (SMB/subscription) and complex, high-touch billing (Enterprise/contract-driven) - or strong experience in one with clear aptitude for the other.

• A high sense of urgency and comfort operating with incomplete tooling while building the better version.

• Strong Excel/spreadsheet skills and experience with modern billing, invoicing, or ERP systems (e.g., NetSuite, Stripe Billing, Zuora, QuickBooks, or similar).

• Excellent judgment on when to hold firm with a customer and when to escalate - especially on Enterprise accounts with contractual complexity.

• Clear, professional written and verbal communication for both internal stakeholders and customer-facing collections conversations.

• Curious and proactive about applying AI to real business problems - biased toward automation and reducing manual work rather than adding headcount to solve volume.

• Comfortable being the operational check on Sales and Customer Success - someone who can translate deal terms, discounts, and promotions into accurate billing setup, and flag gaps before they become revenue leakage or customer disputes.

Nice to Have

• Experience in healthcare, dental, or another regulated vertical with multi-location or DSO-style customer structures.

• Experience partnering with Legal on contract terms that affect billing and collectability.

• Prior people management experience or a track record of being an early hire who later built and led a team.