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.

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.

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.