Jobs at Stillwater Insurance Group (Now Hiring) — 5 open

Join our hardworking, collaborative team where your contributions will be celebrated and valued.

Why Stillwater?
We’re a national insurance provider that offers a full suite of insurance products and services. We strive to be the most respected insurance provider in the United States—and that respect starts with our employees.

About the Role

We are seeking a strategic, results-driven Chief Financial Officer (CFO) to join our executive team and provide financial leadership for a growing property and casualty insurance company. This is a high-impact role for an experienced financial executive who will serve as a key partner to the CEO and executive team, guiding financial strategy, planning, and operations to drive growth and operational excellence. This is an in-office position in our Jacksonville, FL headquarters. 

The ideal candidate will bring deep expertise in financial leadership within professional services, insurance, or recurring revenue businesses, and must be able to quickly learn and adapt to the property and casualty insurance model.

Key Responsibilities

Strategic Leadership

• Lead all financial operations, analytics, and strategy development.
• Partner with the executive team to assess organizational performance against both budget and long-term strategic goals.
• Build tools and systems to deliver actionable financial and operational insights.
• Guide cost management and financial planning aligned with strategic priorities.

Executive Management

• Serve as an integral member of the executive leadership team.
• Participate in strategic decisions, operating model development, and execution.
• Prepare and present Board and AM Best review materials; collaborate with reinsurance brokers on capital adequacy.

Financial Planning & Analysis

• Oversee budgeting, forecasting, and monthly P&L reporting.
• Analyze business results and recommend strategic adjustments.
• Support reinsurance discussions and capital allocation strategies.

Finance & Treasury

• Manage cash flow planning, asset management, and investment reporting.
• Maintain banking and reinsurance broker relationships.
• Implement predictive models to enhance financial decision-making.

Accounting & Compliance

• Oversee accounting and cash receipt functions, ensuring system integrity and compliance.
• Ensure timely, accurate financial reporting and regulatory compliance (including responses to Department of Insurance and data calls).
• Direct internal control maintenance and process improvements.

Audit & Tax

• Lead month-end, quarter-end, and year-end closing activities and GAAP reporting.
• Review tax provisions, IBNR reserve analyses, and statutory reporting.
• Manage relationships with external auditors and ensure audit readiness.

Cash Management & Real Estate

• Oversee cash forecasting, accounts receivable, and weekly disbursements.
• Manage corporate real estate leases and subleases; negotiate terms as needed.

Qualifications

• 10+ years of senior financial leadership experience, including at least 5 years as a CFO or equivalent role in a $100M+ organization.
• Bachelor’s degree in Accounting required; CPA license mandatory.
• Proven knowledge of GAAP and statutory insurance accounting, with preference for Property & Casualty insurance experience.
• Strong leadership, strategic thinking, and analytical skills.
• Excellent communication, presentation, and interpersonal skills.
• Demonstrated success in partnering with executive leadership to implement strategic financial solutions.

Ready to Make an Impact?

Apply today to start your journey of being celebrated and valued with Stillwater Insurance Group.

Offer is contingent upon a favorable response from both a pre-employment background investigation and a drug screen.  

Stillwater Insurance Group is an equal opportunity employer and a drug-free workplace.