Managing Director of Finance

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Director, Recruitment- Plymouth Rock Assurance

We are seeking a results-driven Managing Director of Finance to lead financial management for the Independent Agency Group. Reporting to the Chief Financial Officer, this role will be responsible for overseeing financial planning, budget, and performance analysis across all functions, while serving as a strategic partner to the executive leadership team. The ideal candidate has a strong track record of success in finance roles, preferably within the property & casualty insurance industry, and brings a collaborative, forward-thinking approach to driving financial performance. As our organization continues to grow, we are looking for passionate and driven professionals who share our core values — individuals committed to integrity, intelligence, and excellence.

Responsibilities

• Serving as a trusted advisor to the Independent Agency Group leadership team, providing insights and recommendations to drive profitable growth.
• Leading development and execution of financial plans aligned with the Group’s strategic objectives, including forecasting, business performance reporting, and cost/benefit analysis of investment opportunities.
• Driving continuous improvement in financial processes, reporting capabilities, and planning technologies, including creation of data-driven forecasts.
• Identifying and executing high-impact initiatives to reduce expenses across both group-specific and shared services functions.
• Building strong relationships with key stakeholders across the organization, including Corporate Finance, Actuarial, and other cross-functional partners, to align and deliver on goals.

Qualifications

• Master’s degree in accounting or finance preferred.
• Minimum of 10 years of progressive experience in financial planning, budget, and performance analysis.
• Experience in the property & casualty insurance industry preferred.
• Ability to lead teams and influence across functional areas within and outside of Finance.
• Demonstrated ability to link financial outcomes to business drivers.
• Results orientation with a record of delivering under pressure.
• Excellent verbal and written communication skills, with the ability to convey complex financial concepts clearly and concisely.

About the Company

With more than 40 years of experience, over $2.4 billion in written and managed premium, and nearly 2,000 employees, Plymouth Rock has financial strength, size and stability. At the same time, the company has strived to maintain a highly entrepreneurial and non-bureaucratic culture.

Seniority level

• Seniority level

  Director

Employment type

• Employment type

  Full-time

Job function

• Job function

  Finance, Management, and Strategy/Planning

• Industries

  Insurance

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