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 by core values and operating principles that 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.

How You’ll Do It

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 those 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 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 Engineering to build the systems and automations that streamline collections — automated ordering, tracking data, KPI reporting, and automated action triggers and process steps.
• Translate performance and KPI reporting produced by Pie's internal analytics team into clear, actionable guidance for your team and cross-functional partners — this role interprets and acts on data rather than building the underlying reports.
• Track and drive continuous improvement for bad debt allowance processes, in partnership with Accounting.
• Coordinate dispute resolution cross-functionally and identify upstream process improvements that reduce bad debt exposure.
• Ensure timely closeout for receivables before they reach collections or litigation, and a clean, documented handoff to the Collections team when recovery is required. 
• Partner cross-functionally to ensure trackability, visibility, and assignment inclusion for policy and collection-handling data — the source that powers Collections KPI tracking and management.
• Monitor aging and SLA performance and make or propose escalation and handoff decisions based on defined thresholds, in partnership with the Team Lead, Collections. 

Manage the LEAN partnership and vendor coordination

• Manage the LEAN partnership and BPO / offshore coordination for billing, cash, remittance, and money-out work, including capacity, quality, and SLA performance.
• Collaborate with the internal Business Systems Analyst on the ongoing billing-systems (Zuora) rollout and related billing-automation initiatives.
• Create and maintain vendor and BPO scorecards covering timeliness, quality, accuracy, and other key operating data points — not collection recovery rates.
• Partner with vendors to design and implement quality improvements based on scorecard findings.
• Review and update vendor and BPO guidelines regularly, and communicate any changes, additions, or deletions to partners in a timely manner.
• Manage vendor billing for billing-operations partners. Serve as the primary point of contact for those vendors on escalations and approval requests.
• Research, propose, and vet potential new billing, remittance, or BPO partners as the operating model evolves.
• Partner with the Team Lead, Collections on a defined handoff: when a balance is unpaid after cancel or termination, your team delivers complete billing history, cash activity, and policy status so Collections can pursue recovery. You do not own litigation, settlement, collection-agency placement, or recovery-rate targets. 

Lead and grow the billing team

• Lead, develop, and manage the performance of the billing operations team, including BPO and offshore resources — setting clear benchmarks, coaching to them, and actively managing underperformance through improvement plans up to and including offboarding.
• Develop and maintain SOPs for billing, cash application, remittance matching, dispute handling, and non-pay processing to ensure timely handling and proper receivable closeouts or Collections handoff.
• Establish benchmarks and KPIs for the team and individual contributors, and manage business performance and productivity.
• Drive process improvement and optimization of existing processes through Agile methodology.
• Manage onboarding, ongoing training and development, and offboarding for team members. Coordinate training strategy and identify growth areas in partnership with Enablement and Learning and Organizational Development.
• Serve as an escalation point for complex customer, agency, and partner inquiries, questions, and disputes. 

The Right Stuff

• A high school diploma or GED is required. An Associate's or Bachelor's degree is preferred.
• 3+ years of team leadership or people management experience, including managing performance, required.
• 3+ years of experience in billing, cash application, accounts receivable operations, or insurance operations required. Commercial insurance billing preferred.
• 1+ year of Premium Audit or payroll-partner (ADP, RPM, or similar) remittance experience preferred.
• 2+ years of vendor management experience required.
• 1+ year of experience managing BPO or offshore teams preferred.
• 1+ year of experience with data analysis and an understanding of workers' comp operational practices required. A strong understanding of Pie's products and systems is required.
• LEAN Certification preferred.
• Working knowledge of billing, invoicing, cash application, and cancellation-notice processes required. Familiarity with how unpaid balances move to collections is helpful.
• Communicate clearly and convincingly in writing and out loud, present your own views, and make requests directly and openly. You close the loop, and you give and receive feedback with empathy. You bring professional maturity, customer empathy, and an owner's attitude. You can support month-end billing close with documented, back-testable assumptions and the evidence Accounting needs.
• Analyze and solve simple to complex problems independently and use data to make informed decisions. You design win-win solutions with creativity and good judgment, challenge the status quo, and apply agile thinking — testing ideas, iterating on findings, and refining before you launch the full solution.
• Learn from mistakes, aim to be better tomorrow than today, and raise the performance bar. You seek to understand, stay open to new information and change, and question assumptions while applying new context. 
• Demonstrate interpersonal awareness — considering the needs of others, building collaborative relationships, and respecting individual and cultural differences. You gain cooperation by delivering results and building buy-in.
• Comfortable with G-Suite tools, Salesforce, collaboration tools (Slack preferred), and billing platforms (Zuora, Stripe, lockbox workflows preferred).
• Take responsibility for your own tasks, deliverables, and timelines with strong self-direction.
• Intermediate data reporting and analytic skills — enough to pull team and vendor scorecard data, analyze it, and bring recommendations to BPO partners, payroll partners, and Premium Audit.
• Intermediate organizational skills to track progress against SLA and vendor expectations and pivot between platforms frequently.

The use of AI in Application Review: To support a fair, efficient, and consistent hiring process, we use AI-powered tools to assist in the initial screening of applications. These tools help us identify qualifications and prior work experiences that align with the requirements of the role. We may also use AI assistant video tools during interviews to support note-taking and candidate evaluation. All AI-powered outputs are still subject to human oversight and decision-making at multiple stages of the process. By submitting your application, you acknowledge and consent to Pie utilizing these AI technologies to assist in our evaluation process.

Base Compensation Range$70,000—$85,000 USD

Compensation & Benefits 

• Competitive cash compensation
• Comprehensive health plans
• Generous PTO
• Future focused 401k match
• Generous parental and caregiver leave
• Our core values are more than just a poster on the wall; they’re tangibly reflected in our work 

Making every part of working with us "Easy as Pie" - including our offer process. When we find someone we'd like as a Pie-oneer (a member of our team), we move quickly to put together a fair offer based on your skills, experience, location, and compensation expectations.

Each year Pie reviews company performance and may grant discretionary bonuses to eligible team members.

Location Information 

Unless otherwise specified, this role is remote. Remote team members must live and work in the United States (territories excluded) and have access to reliable, high-speed internet.

Additional Information

Pie Insurance is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, marital status, age, disability, national or ethnic origin, military service status, citizenship, or other protected characteristic.

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Safety First: Pie Insurance is committed to your security during the recruitment process. We will never ask you for credit card information or ask you to purchase any equipment during our interview or onboarding process.

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