Position Summary:
Prestige Trucking Insurance is seeking a seasoned Chief Financial Officer to lead its corporate accounting function. The CFO is responsible for overseeing all of the companies in the conglomerate’s accounting functions to ensure timely, accurate, and compliant reporting. This role manages the accounting team responsible for the accounting life cycle from end to end and is also responsible for implementing financial audit procedures. The CFO works closely with operations, finance, and external vendors to optimize the financial reporting and accounting processes. The ideal candidate will bring a blend of technical accounting expertise, operational leadership, and a proactive mindset.
Essential Duties and Responsibilities:
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Develop and oversee the Accounting Department, including setting structure, goals, and performance standards.
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Lead and manage all accounting operations including billing, AR/AP, payroll, inventory, and general ledger
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Support budgeting, forecasting, and strategic financial planning
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Ensure compliance with federal, state, local, and insurance regulatory bodies tax requirements
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Ensure the timely payment of all invoices and bills
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Oversee the monthly, quarterly, and year-end financial reports and closing of the books
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Prepare financial statements on a regular basis and ad-hoc as needed for business reasons
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Build, train, and mentor a team of Accountants and Bookkeepers
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Act as a liaison with IT for finance system optimization
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Design audit processes to ensure payments are accurately made and no over or under payments occur
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Collaborate with other division/business unit leaders to analyze their cost activities and identify opportunities for efficiency
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Support budgeting, forecasting, and strategic financial planning
Knowledge / Skills / Abilities (KSA’s):
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Strategic & Operational Leadership Ability – Ability to set and execute long-term financial strategy while providing hands-on leadership and oversight of day-to-day accounting and financial operations across a multi-entity organization.
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Business & Financial Acumen – Comprehensive understanding of financial drivers, insurance operations, and organizational performance, with the ability to evaluate complex business scenarios and guide executive-level decision-making.
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Analytical & Problem-Solving Skills – Advanced ability to interpret complex financial data, assess risk, identify trends or inefficiencies, and develop and implement effective financial and operational solutions.
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Cross-Functional Management Ability – Ability to lead and collaborate across functional areas, including operations, IT, external vendors, and executive leadership, to align financial strategy with business objectives and improve enterprise performance.
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Integrity & Accountability – Demonstrated commitment to ethical financial leadership, accuracy in reporting, regulatory compliance, and personal accountability for financial outcomes and controls.
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Confidentiality & Professional Discretion – Proven ability to handle highly sensitive financial, legal, and organizational information with the highest degree of discretion, professionalism, and confidentiality.
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Organizational & Time Management Skills – Exceptional ability to manage competing priorities, complex reporting timelines, and high-stakes deliverables while maintaining accuracy and consistency during audits, financial closes, and strategic initiatives.
Minimum Qualifications:
Required:
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12-15 years of progressive accounting experience (preferably in insurance).
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With at least 3 years of experience as a controller and in leading a team
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In-depth understanding of financial reporting, insurance accounting, and GAAP requirements
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Strong leadership, mentoring, and organizational skills.
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CPA License Required
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Automation focus and experience in automating processes
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Bachelor’s or Master’s degree in Accounting, Finance, or Business Administration
Preferred:
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Experience in accounting for insurance operations ideally trucking insurance operations or public accounting experience with franchise accounting experience
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Familiarity with agency management systems (Salesforce, Now Certs, or Similar)
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Familiarity with Accounting Systems (Quick Books, Sage, Salesforce, or similar)
Physical Demands and Work Environment:
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Office-based with standard business hours.
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Occasional extended hours during audits, month/quarterly/year end, or operational rollouts.
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Limited travel required for vendor, carrier, or regulatory meetings.
Standard business hours are typically 9am-6pm.
