Senior Manager, Financial Reporting & Compliance - 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.

This leadership role, reporting to the VP of Billing and Collections, serves as the authoritative source for all billing, collections, and payments performance data at Pie Insurance. The Senior Manager is responsible for delivering accurate, timely, and actionable financial reporting, and for enforcing robust controls and compliance across Pie's Workers' Compensation and Commercial Auto billing operations.

The role encompasses the entire reporting lifecycle—from data extraction and reconciliation to executive-level dashboarding. Key areas of ownership include Accounts Receivable (AR) aging, collections effectiveness, payment lifecycle analytics, bad debt tracking, and audit invoice management. This position provides essential support for month-end close, balance sheet integrity, internal controls compliance, and external audits, requiring close collaboration with Finance, Accounting, Operations, and Product teams.

How You’ll Do It

Core Responsibilities: Financial Reporting & Accounts Receivable (AR) Analytics

• Own the Aged Trial Balance (ATB): Maintain the authoritative ATB, ensuring accuracy, timeliness, and alignment with the Finance department.
• Support Allowance for Doubtful Accounts (AFDA): Provide insights through trend analysis, risk segmentation, and collections performance data.
• Generate Comprehensive AR Reports: Produce detailed AR aging reports segmented by product line, payment method, payment plan, and risk indicators.
• Develop Collections Performance Dashboards: Create weekly and monthly reports on recovery rates, delinquency, payment success/failure rates, NSF/chargeback volumes, and bad debt projections.
• Manage Audit Invoice Reporting: Track premium true-ups, audit payment success rates, and outstanding receivables across all products.
• Deliver Financial Analysis: Prepare trend and variance reporting for Management Business Reviews (MBRs), forecasting, and executive operational reviews.

Payment Lifecycle Management & Cost Analysis

• Establish Payment Source of Truth: Centralize data for all payment activity, including pay-by-pay records, Payment Service Provider (PSP) performance, settlement accuracy, remittances, and recurring payment behavior.
• Ensure Data Integrity: Guarantee 100% accuracy between billable activity, collected payments, and General Ledger (GL) balances.
• Analyze Payment Mix and Costs: Track payment method mix (ACH, credit card, debit card, check), transaction volumes, channel effectiveness, and the total cost of payments (e.g., Stripe fees, chargeback expenses, collection agency commissions).
• Quantify Payment Failures: Assess the financial impact of failed payments, retry logic performance, and down payment effectiveness.
• Monitor Churn & Retention: Analyze billing, collections, and payment behavior impacts on customer retention and churn.

Collections Performance & Strategy Visibility

• Report on Collections Effectiveness: Provide comprehensive reporting on internal vs. third-party collections, including placement effectiveness, recovery rates, and cost-to-collect.
• Track Key Collections Metrics: Monitor NOC rates, payment success rates, policy survival rates, and retention by cohort.
• Analyze Outcomes: Segment collections outcomes by age, balance, payment method, underwriting segment, and agency performance.
• Develop Predictive Models: Build models and scenario analyses to inform collections strategy and resource allocation.
• Identify Bad Debt Risk: Establish early warning indicators for bad debt and support segmentation strategies to maximize recovery.

Month-End Close & System Reconciliation

• Lead Monthly AR Close: Direct monthly activities including AR aging validation and bad debt allowance analysis in collaboration with Accounting.
• Execute Critical Reconciliations: Perform reconciliations between core systems (Zuora, Stripe, Salesforce, PPS, Nexus Audit, and GL).
• Resolve Discrepancies: Identify, investigate, and resolve reconciliation breaks, payment misallocations, and system discrepancies.
• Document Adjustments: Maintain documentation and tracking for premium adjustments, refunds, write-offs, and billing corrections.
• Support Audits: Provide clean data packages and var