Team Lead, Billing & Collections

Pie's mission is to empower small businesses to thrive by making commercial insurance affordable and as easy as pie. We leverage technology to transform how small businesses buy and experience commercial insurance. Like our small business customers, we are a diverse team of builders, dreamers, and entrepreneurs who are driven bycore values and operating principlesthat guide every decision we make.

As the Team Lead, Billing & Collections, you own billing accuracy, cash application, and the non-pay lifecycle — notice of cancellation, rescission, reinstatement, and termination — so premium, coverage, and AR stay reconciled. You lead the billing operations team that invoices, applies cash, matches partner remittance, and processes cancels and reinstatements across installment billing, payroll-partner remittance, lockbox, and Stripe. You are accountable for SLA and quality outcomes on that work, not for post-handoff recovery.

Past-due collection strategy, litigation, settlement, and collection‑vendor performance sit with the Team Lead, Collections. You work hand‑in‑hand with that team so unpaid balances are handed off cleanly, on time, and with the documentation Collections needs.

You’ll lead individual contributors alongside BPO and offshore partners, set the operating standard for how every dollar is billed and applied, and find upstream improvements that reduce Pie's exposure before a receivable ever reaches collections. You set and enforce service‑level agreements across billing, cash, remittance, and the non‑pay lifecycle, and you are accountable for the performance of your team, your vendors, and your BPO and offshore partners against defined KPIs.

You partner with Accounting on month‑end billing close, unapplied cash, and the documentation Finance needs to reconcile the books. You partner with Product, Engineering, and the Business Systems Analyst on Zuora and billing automation. This is a role for someone who wants to own a function, build it, and be measured on results.

Own billing accuracy, cash application, and the non-pay lifecycle

Own Pie's bad debt recovery rate. You'll own billing integrity across installment invoices, short‑rated policies, claim deductibles, audit surcharge fees, and additional premium from mid‑term endorsements or end‑of‑policy audits — so invoices are accurate before they become a collection problem.

Set and enforce service‑level agreements across the full collection lifecycle — from receivable handoff and outreach cadence through referral timing and final closeout — and hold your team, vendors, and BPO and offshore partners accountable to these SLAs and KPIs.

Own cash application and partner remittance matching, and the full non‑pay lifecycle — notice of cancellation, rescission, reinstatement, and termination processing — as a daily control point keeping cash, coverage, and AR reconciled.

Own and continuously improve the work assignment across billing, remittance, cash, and non‑pay queues, including BPO and offshore capacity, so unpaid installment invoices, surcharge fees, and final invoices following audit close are handled on SLA before they age into collections.

Prioritize collection effort on a risk basis, focusing attention on the large and jumbo balances that drive the majority of exposure.

Make sure every call, letter, and text complies with the FDCPA, Regulation F, the TCPA, and applicable state debt‑collection laws. Partner with Compliance and Legal on consent, opt‑out, and disclosure requirements.

Serve as the top‑level point of contact for billing, cash‑application, remittance, and non‑pay issues, complaints, and escalations, acting as subject matter expert and business stakeholder advocate within Pie.

Partner with Product and…