Senior Financial Reporting & Compliance Manager, Pie Insurance
Billing & Collections
$130-165k
+ Equity
SQL
Tableau
Looker
Excel
Google Sheets
Salesforce
Power BI
Zuora
Senior and Expert level
Remote from US
Small business insurance
Be an early applicant
Small business insurance
201-500 employees
FintechB2BInsurance
Be an early applicant
$130-165k
+ Equity
SQL
Tableau
Looker
Excel
Google Sheets
Salesforce
Power BI
Zuora
Senior and Expert level
Remote from US
201-500 employees
FintechB2BInsurance
Company mission
To make insurance less expensive, simpler, and more transparent for small business owners.
Role
Who you are
- 7+ years in financial analytics, data reporting, or AR operations in technology-driven environments
- Public accounting (Big 4 or large regional) / consulting experience highly preferred
- Proficiency in SQL for querying enterprise data warehouses and building financial and operational reports directly from structured data sets
- Hands-on experience building dashboards and executive-level reports in Looker (preferred), Power BI, or Tableau
- Experience working with enterprise data warehouses and collaborating with Data Engineering or Analytics teams to source, validate, and operationalize financial reporting data
- Workers' Compensation insurance billing experience is highly advantageous
- Expert proficiency in Excel/Google Sheets (pivot tables, complex formulas, VLOOKUP/XLOOKUP, data visualization)
- Comfort and fluency working with and manipulating structured and unstructured data sets
- Exceptional reconciliation skills, with the proven ability to investigate and resolve complex, multi-system discrepancies
- Experience with billing/payment platforms (Zuora, Stripe, Salesforce preferred) and the ability to extract and analyze data from various sources
- Working knowledge of GAAP principles, AR fundamentals, and financial controls
- Knowledge of internal control program compliance requirements and financial audit processes
- Demonstrated experience reconciling complex payment ecosystems (PSPs, remittances, recurring payments)
- Highly analytical, detail-oriented mindset with an unwavering commitment to data accuracy
- Excellent communication skills, capable of translating technical findings for non-technical audiences and creating high-level executive dashboards
- Comfortable building structure and clarity in ambiguous or nascent environments
What the job involves
- 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
- 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 variance explanations for quarter-end and year-end audit requests
- Controls, Compliance & Audit Support
- Execute Internal Controls: Perform Internal controls for financial reporting, including documentation, testing, and remediation of control deficiencies
- Maintain Balance Sheet Integrity: Establish robust reporting controls and reconciliation frameworks
- Manage Audit Trails: Maintain comprehensive audit trails for all financial adjustments, write-offs, and manual system interventions
- Support Audits: Facilitate internal and external audit requests with accurate data samples and process walkthroughs
- Ensure Compliance: Confirm compliant reporting of unclaimed property, refund reserves, and customer fund handling
- Identify and Improve Controls: Identify control gaps and recommend improvements to processes, tooling, or policy
- Document Procedures: Maintain documentation for reporting processes, system access controls, and reconciliation procedures
- Data Quality & System Integration
- Ensure Data Integrity: Uphold data integrity across all billing platforms (Zuora, Stripe, Salesforce, PPS, Nexus Audit)
- Resolve Data Issues: Identify and resolve systematic data issues that compromise financial reporting accuracy
- Support Modernization: Assist Billing Modernization initiatives by validating data migration, testing new reporting outputs, and documenting updated workflows
- Enhance Automation: Partner with Product, Engineering, and Data teams to improve automated reporting capabilities
- Document Methodology: Maintain data dictionaries, field definitions, and reporting methodology documentation
Our take
Historically, it’s been extremely cumbersome to qualify, onboard and manage workers’ comp insurance, particularly for America’s small businesses which haven’t been prioritized by larger carriers. That’s left small businesses often stranded with expensive and low-quality coverage.
Pie Insurance is changing all that through its technology-first model. Using data and analytics to better comprehend risk and speed up the decision-making process, it reduces the time to make an underwriting decision to a few minutes. Facing only legacy competition in an industry ripe for disruption, Pie Insurance has enjoyed rapid growth and received significant investment funding from backers in the InsurTech space.
Having recently acquired a nationally licensed insurance company, Pie Insurance is now able to directly issue its own policies nationwide. Currently available in 38 states, it will be aiming to expand its operations into the remaining states and territories to provide insurance to small businesses across the entire USA.
Freddie
Company Specialist at Welcome to the Jungle
Insights
Top investors
4% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Sep 2022
$315m
SERIES D
Mar 2021
$118m
SERIES C
Total funding: $620.3m
Company benefits
- Flexible work: Pie offers in-office, hybrid, and remote work options so you can create the work environment that's best for you
- Fully paid health care: Pie covers the health, vision, and dental premiums for full time employees and covers a percentage of premiums for spouses and children
- Equity and 401k: We think you should get a piece of the pie, so in addition to equity, Pie contributes to your retirement through a 401k
- Generous PTO: We want to make sure Pie-oneers have time to balance a rewarding work life and fulfilling personal life
- Parental leave: Pie knows your family is important, providing 100% compensation for the first three months of parental leave, as well as a generous return to work plan
- Caregiver leave: Pie offers caregiver leave so you have the time to dedicate to those who need your care
- HSA and Health FSA: Pie contributes $1,500 for individuals and $2,000 for family HSAs per year. Employees have the option to contribute to a Health FSA
- Dependent Care FSA: To help care for your dependents, Pie allows employees to set aside pre-tax dollars to be used for expenses like babysitters, daycare, summer camps, etc
- Pet insurance: Pie understands your pet is family and their care can be costly when they're not feeling well. The plans provide reimbursement for common needs like exams, vaccines, x-rays, prescriptions, and much more!
Company HQ
Union Station, Denver, CO
Leadership
John Swigart
(Co-Founder & CEO)Previously CMO for RapidFinance. Also worked as CMO for Esurance, starting off as VP of Finance in 2000.
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