Chief Financial Officer

Frank Winston Crum Insurance • Clearwater, FL

8d • Onsite

About The Position

FrankCrum is seeking a full-time, on-site Chief Financial Officer (CFO). This senior executive role is responsible for enhancing financial performance, strategic decision-making, capital stewardship, and increasing long-term enterprise value. The CFO will report to the President of Frank Winston Crum Insurance (FWCI) and will lead the Finance, Accounting, Actuarial, Compliance, and Data & Analytics departments. This position serves as a critical advisor to the President, the executive leadership team, and the Board. The CFO will provide forward-looking insights into the organization's performance, identify opportunities, and assess risks, translating strategic goals into measurable financial and operational plans. This role requires not only strong financial expertise but also a commercial mindset within the insurance industry, understanding the interplay of underwriting, pricing, claims, reserving, reinsurance, operations, technology, and distribution for sustainable profitability. The ideal candidate will be able to challenge assumptions constructively, strengthen executive accountability, and guide the business in proactively addressing emerging risks and opportunities.

Requirements

• Bachelor's degree in Finance, Accounting, Economics, Actuarial Science, Business Administration, or a related field.
• 10+ years of progressive experience in finance, accounting, actuarial, or insurance-related leadership roles.
• 5+ years in a CFO, Deputy CFO, SVP Finance, VP Finance, or comparable senior leadership role strongly preferred.
• Direct experience with an insurance carrier in a senior financial leadership capacity required.
• Demonstrated record of improving profitability, forecasting accuracy, capital efficiency, operating discipline, financial transparency, or enterprise value in a complex insurance organization.
• Demonstrated experience leading meaningful financial or operational transformation, including upgrading talent, improving processes, implementing technology, and increasing the quality and speed of management information.
• Experience with P&C insurance, workers' compensation, commercial insurance, or a similarly regulated insurance environment preferred.

Nice To Haves

• MGA (Managing General Agency) experience, particularly experience with underwriting, delegated authority, pricing, profitability, and carrier/MGA relationships preferred.
• Experience leading or directly overseeing Actuarial is strongly preferred given the scope of this role.
• Experience presenting financial, actuarial, risk, and strategic matters to a Board of Directors and/or executive leadership team preferred.
• Experience with acquisitions and divestitures, strategic partnerships, debt and capital arrangements, economic capital, stress testing, and post-investment performance measurement.

Responsibilities

• Develops and executes the organization's long-term financial strategy in partnership with the President, FWCI and executive leadership team.
• Translates business strategy into financial plans, budgets, forecasts, capital requirements, and measurable performance objectives.
• Serves as a trusted strategic advisor to the President, FWCI, executive leadership team, and Provides insight into the Board’s financial performance, risks, opportunities, and business scenarios.
• Leads the organization's Finance, Accounting, Actuarial, Compliance, and Data & Analytics functions, driving modernization through improved processes, automation, analytics, technology, data, and artificial intelligence.
• Leads the financial evaluation and execution of acquisitions, strategic partnerships, new ventures, major technology investments, and other enterprise initiatives, including valuation, scenario analysis, due diligence, capital requirements, risk assessment, and post-investment performance measurement.
• Ensures accurate, timely, and transparent financial reporting in accordance with GAAP, statutory, regulatory, and governance requirements.
• Oversees financial planning, budgeting, forecasting, long-range planning, and actuarial processes, ensuring alignment between financial projections, business strategy, and risk assumptions.
• Leads the Actuarial function and oversee reserving, forecasting, pricing support, financial modeling, loss projections, and actuarial analysis.
• Partners with underwriting, claims, product, operations, and risk leadership to evaluate insurance performance, profitability, pricing, and financial trends.
• Monitors key insurance and financial metrics, including premium growth, loss and expense ratios, combined ratio, reserve development, profitability, and performance by product or business segment.
• Oversees capital, liquidity, investment, reinsurance, and financial risk strategies to support the organization's financial strength and long-term objectives.
• Evaluates and strengthen capital strategies, investments, strategic partnerships and initiatives, new products and markets, and other significant business decisions to ensure appropriate financial returns and risk management.
• Identifies opportunities to improve profitability, operating efficiency, productivity, margins, and return on investment across the organization.
• Establishes strong financial controls, policies, processes, compliance practices, and governance while maintaining effective relationships with auditors, regulators, banking partners, and other external stakeholders.
• Provides leaders with actionable financial, actuarial, compliance, risk, and business insights, helping them understand performance drivers, risks, opportunities, and the actions needed to improve results.
• Builds and lead high-performing Finance, Accounting, Actuarial, Compliance, and Data & Analytics teams, establishing clear accountability, leadership development, succession planning, and a culture of collaboration and continuous improvement.
• Represents the organization with the Board, regulators, auditors, financial institutions, and other key stakeholders, communicating complex financial, actuarial, and strategic matters clearly and effectively.

Benefits

• Health Insurance is just twenty-five dollars per month for employee only coverage and a very low cost for family levels.
• Dental and Vision Insurance
• Short Term Disability and Term Life Insurance at no cost to the employee
• Long Term Disability and Voluntary Term Life Insurance
• Supplemental insurance plans such as Accidental, Critical Illness, Hospital Indemnity, Legal Services and Pet Insurance
• 401(k) Retirement Plan where FrankCrum matches 100% of the first 4% the employee contributes, and the employee is immediately vested in the employer match
• Flexible Spending Accounts for Medical and Dependent Care Reimbursement
• Health Savings Account funded by FrankCrum
• Paid time off and holiday pay
• Education Benefit Program at the IRS Maximum allowance
• PTO cash out
• Tickets at Work
• Alero Financial and its robust credit union benefits program
• Employee and client referral bonus programs
• Disaster Relief Fund for employees

What This Job Offers

• Job Type: Full-time
• Career Level: Senior