Director of Finance (Insurance)

Understory, Inc.; Madison (WI); Remote; USD 180,000 - 240,000; Full time

Job summary

Understory, Inc. is seeking a Director of Finance to own the financial reporting and controls for our growing program insurance business. This remote-friendly role reports to the CFO and partners with the Controller, building the function in year one while planning to scale the team as needed.

You will own the close, consolidate numbers, and produce internal/external reports, KPI packages, and board materials, while driving budgeting, forecasting, and cash runway analysis.

Qualifications

• CPA required.
• 8+ years in accounting and finance, including public accounting.
• Insurance accounting experience (MGA, program, fronting or carrier) and familiarity with ceded reinsurance.
• Ownership of a full close, from consolidation to reporting.
• Technical research and position memos for US GAAP.
• Budgeting, forecasting, and modeling from drivers (Excel proficiency).
• Clear communication to non-accountants in plain English.

Responsibilities

• Own financial reporting: monthly package, KPI pack, board materials, US GAAP statements, and lender requirements.
• Manage the close process and consolidation, ensuring sign-off.
• Document finance processes and build controls and segregation of duties.
• Research US GAAP issues and write position memos; defend positions with auditors.
• Lead FP&A: annual budget, rolling forecasts, variance analysis, cash forecasting.
• Oversee treasury activities: banking, surplus cash investments.
• Oversee interim HR processes until hiring expands the team.

Skills

CPA

8+ years

Insurance accounting

Close ownership

Technical research

Budgeting

Forecasting

Excel modeling

Writing

Job description

The role

We are a growing program insurance business and we are hiring the person who will own how we account for it and report on it. This is a remote-friendly role located in the United States.

The Director of Finance reports to the CFO and works alongside a Controller as an equal peer. The Controller runs day-to-day financial operations and the flow of funds; this role owns what the numbers mean, how they are reported, and the controls around them. Until the team is larger, the two review each other’s work.

This is a build, not a maintain. You will do most of it yourself in year one and hire behind you as the work allows.

What you will own

• Financial reporting. All internal and external reporting — the monthly package, the KPI pack, board and investor materials, annual US GAAP statements with footnotes, and what lenders, reinsurers and carrier partners require under their agreements.
• Close. The close calendar, the standard each task has to meet, and sign-off. The Controller executes it; you manage the consolidation process, approve the result and report from it.
• Process and controls. Document every finance process and build the control matrix over it. Own segregation of duties and authorization limits, and design manual reconciliation out where the architecture allows.
• Technical accounting. Research US GAAP questions and write position memos. Own the judgment areas — commission revenue including contingent and variable consideration, ceded reinsurance, premium receivable and payable presentation, gross versus net, collateral and restricted cash. Maintain the accounting policy manual and advise on new programs and contracts before they are signed.
• Audit and tax. Both external relationships — the audit timetable and the PBC list, and the tax firm on filings, the provision, state registrations and the indirect obligations the business carries.
• FP&A. The operating model, the annual budget, a rolling forecast re-cut as actuals land, and monthly variance analysis. Cash forecasting and runway, including the working‑capital swings that settlement cycles and collateral create.
• Treasury. The banking structure, borrowing and the investment of surplus cash.
• Interim HR. The HR function until the company is large enough to staff it — the employee lifecycle, benefits and the annual renewal, the handbook and policy.

You will hire and develop the team as the work justifies it.

What we are looking for

Required Qualifications

• CPA.
• 8+ years in accounting and finance, including public accounting. Audit experience in an insurance practice is the strongest preparation.
• Insurance accounting — MGA, program, fronting or carrier. Comfortable with ceded reinsurance, commission structures including contingent arrangements, premium receivable and payable, and collateral.
• Ownership of a full close, not participation in one.
• Technical research you can point to: standards applied, memos written, positions defended to an auditor.
• Budgeting, forecasting and modeling built from drivers, in Excel at a level you can be tested on.
• Writing. A material part of this job is explaining a number or a position in plain English to people who are not accountants.

Preferred Qualifications

• Statutory accounting or insurance regulatory reporting.
• An ERP or accounting‑system implementation you helped select and run.
• Working with outsourced accounting providers and holding them to a standard.
• A first close calendar, a first audit, or a first finance hire built somewhere before.

How you work

You write things down. You chase a difference until you find it rather than plugging it. You say when a number is an estimate and when it is not. You are willing to tell the CFO something is wrong, including when you built it.

Equal employment opportunity

We are an equal opportunity employer. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, veteran status, genetic information, marital status, pregnancy, or any other characteristic protected by federal, state or local law. We provide reasonable accommodation to applicants and employees with disabilities. Tell your recruiter and we will arrange it.