Director of Finance - Mainstreet (Personal Lines) & Medicare

The Baldwin Group is an award-winning entrepreneur-led and inspired insurance brokerage firm delivering expertly crafted Commercial Insurance and Risk Management, Private Insurance and Risk Management, Employee Benefits and Benefit Administration, Asset and Income Protection, and Risk Mitigation strategies to clients wherever their passions and businesses take them throughout the U.S. and abroad. Mainstreet: Providing best-in-class personal, commercial and life solutions to mass affluent individuals and businesses in their communities, largely through embedded channel partnerships. Medicare: Network of agents providing consultation and healthcare solutions to Medicare eligible individuals.

The Director of Finance plays a pivotal leadership role in ensuring the financial stability, integrity, and long-term success of our insurance brokerage. As the firm’s financial strategist, this position oversees all financial operations and planning, drives compliance, provides critical analysis for executive decisions, and guides team excellence—aligning fiscal health with growth opportunities in a highly regulated and competitive industry.

PRIMARY RESPONSIBILITIES:

• Lead the financial planning process by analyzing company performance, risks, and growth opportunities.

• Oversee all forecasting, and financial reporting functions; ensure accuracy and timeliness of reports for management and the board.

• Assist leading work efforts to identify and improve emerging business data needs and management to help create KPI and key data to help business decisions

• Conduct strategic financial analysis, forecasts, and modeling to support executive decision-making and business reviews.

• Develop, manage, and monitor annual budgets, tracking variances and recommending corrective actions as needed.

• Acts as a business enabler, with a deep understanding of the operations of the business and the interaction of how business decisions are affecting financial outcomes.

• Guide audit and internal control operations, ensuring adherence to financial laws, guidelines, and regulatory compliance specific to the insurance sector.

• Interface with external auditors, regulatory authorities, and financial institutions to maintain organizational compliance and best practices.

• Foster a culture of transparency, accountability, and alignment of financial goals with operational execution.

EDUCATION & EXPERIENCE:

• Bachelor’s degree in Accounting, Finance, or a related field required; Master’s, MBA, or advanced degree preferred.

• 7–10+ years of progressive experience in finance leadership roles, preferably within insurance or financial services.

• Expertise in corporate finance principles, financial analysis, budgeting, and forecasting.

• Strong command of regulatory frameworks, internal controls, and audit procedures applicable to insurance brokerage.

• Proficiency with ERP, financial management, and reporting software (such as Workday, SAP, Oracle, or similar).

• Exceptional communication, presentation, and board-level reporting skills.

• Demonstrated analytical acumen, strategic thinking, and leadership agility.

• Outstanding organizational, problem-solving, and interpersonal abilities, with resilience and integrity under pressure.

• Ideal candidate will have experience working in Insurance, Insurance Brokerage or Medicare business

Team Management Responsibilities

• Direct and mentor finance staff, including accountants, finance managers, and auditors.

• Build a high-performance team culture, establish clear targets, and conduct regular performance reviews to ensure professional development and operational excellence.

IMPORTANT NOTICE:

• This position description is intended to describe the level of work required of the person performing in the role and is not a contract.  The essential responsibilities are outlined; other duties may be assigned as needs arise or as required to support the organization.  All requirements may be subject to reasonable accommodation to applicants and colleagues who need them for medical or religious reasons.

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The Baldwin Group will not accept unsolicited resumes from any source other than directly from a candidate who applies on our career site. Any unsolicited resumes sent to The Baldwin Group, including unsolicited resumes sent via any source from an Agency, will not be considered and are not subject to any fees for any placement resulting from the receipt of an unsolicited resume.