Controller

Job Description

Job Description

Position Summary:

Prestige Trucking Insurance is seeking a seasoned Controller to lead its corporate accounting function. The controller 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 controller 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 / Responsibilities:

• Develop and oversee the Accounting Department, including setting structure, goals, and performance standards.
• Lead and manage all accounting operations including billing, AR/AP, payroll, inventory, and general ledger
• Support budgeting, forecasting, and strategic financial planning
• Ensure compliance with federal, state, local, and insurance regulatory bodies tax requirements
• Ensure the timely payment of all invoices and bills
• Oversee the monthly, quarterly, and year-end financial reports and closing of the books
• Prepare financial statements on a regular basis and ad-hoc as needed for business reasons
• Build, train, and mentor a team of Accountants and Bookkeepers
• Act as a liaison with IT for finance system optimization
• Design audit processes to ensure payments are accurately made and no over or under payments occur
• Collaborate with other division/business unit leaders to analyze their cost activities and identify opportunities for efficiency
• Support budgeting, forecasting, and strategic financial planning

Knowledge / Skills / Abilities (KSA’s): 

• Strategic & Operational Leadership Ability – Ability to provide both strategic direction and hands-on operational oversight for the accounting function, aligning financial operations with organizational goals while managing day-to-day execution across multiple entities.
• Business & Financial Acumen – Strong understanding of business drivers, financial performance indicators, and insurance operations, with the ability to translate financial data into actionable insights that support executive and operational decision-making.
• Analytical & Problem-Solving Skills – Ability to analyze complex financial information, identify trends, variances, and risks, and develop practical, data-driven solutions to financial and operational challenges.
• Cross-Functional Leadership Ability – Ability to effectively lead and collaborate with cross-functional teams, including operations, finance, IT, and external partners, to improve financial processes, efficiency, and organizational outcomes.
• Integrity & Accountability – Demonstrated commitment to ethical financial practices, accuracy in reporting, compliance with regulations, and personal accountability for the quality and reliability of all financial information.
• Confidentiality & Discretion – Proven ability to handle sensitive financial, employee, and business information with the highest degree of confidentiality, professionalism, and discretion at all times.
• Organizational & Time Management Skills – Exceptional ability to manage multiple priorities, meet tight deadlines, and maintain accuracy and control during high-volume or high-pressure periods such as audits, financial closes, and reporting cycles.

Minimum Qualifications:

Required:

• 7-10 years of progressive accounting experience (preferably in insurance).
• With at least 3 years of experience as a finance/accounting manager or controller and in leading a team
• In-depth understanding of financial reporting, insurance accounting, and GAAP requirements
• Strong leadership, mentoring, and organizational skills.
• CPA License Required
• Automation focus and experience in automating processes
• Bachelor’s or Master’s degree in Accounting, Finance, or Business Administration

Preferred:

• Experience in accounting for insurance operations ideally trucking insurance operations or public accounting experience with franchise accounting experience
• Familiarity with agency management systems (Salesforce, Now Certs, or Similar)
• Familiarity with Accounting Systems (Quick Books, Sage, Salesforce, or similar)

Physical Demands and Work Environment:

• Office-based with standard business hours.
• Occasional extended hours during audits, month/quarterly/year end, or operational rollouts.
• Limited travel required for vendor, carrier, or regulatory meetings.