Chief Strategy Officer

Job Title : Chief Strategy Officer (CSO)

Reports To : Chief Executive Officer (CEO)

About New Canaan Insurance Agency

New Canaan Insurance Agency is a respected and client-centered firm providing personalized insurance solutions that protect families, businesses, and communities. With a strong foundation of trust and service excellence, we are entering an exciting phase of strategic growth. We're looking to evolve key internal capabilities—particularly in finance—to support long-term expansion and innovation.

Position Overview

The Chief Strategy Officer (CSO) will serve as a senior advisor to the CEO and play a pivotal role in driving the strategic direction and transformation of New Canaan Insurance Agency. A key focus of this role will be partnering closely with the finance department to elevate its structure, systems, and capabilities—transforming it into a world-class financial organization that supports scalable growth and operational excellence.

This is a unique opportunity for a strategic leader with a strong finance background and a proven track record in shaping business strategy, improving financial performance, and leading cross-functional initiatives in complex environments.

Key Responsibilities Strategic Planning & Business Growth

• Lead the development and execution of the agency's long-term strategic plan in partnership with the CEO and executive team.
• Identify and evaluate growth opportunities including new markets, service lines, partnerships, and acquisitions.
• Translate high-level strategic priorities into actionable plans and roadmaps.

Finance Transformation Leadership

• Serve as a thought partner and advisor to the CFO and finance team in modernizing financial operations, reporting, budgeting, and performance management.
• Help define and implement best-in-class financial processes, systems, and controls to support data-driven decision-making.
• Support the design of financial KPIs and dashboards to track business performance and ensure financial discipline across the organization.

Organizational Alignment & Execution

• Ensure that business units and internal departments are aligned with the strategic and financial objectives of the agency.
• Lead enterprise-wide initiatives that improve operational efficiency, customer experience, and profitability.

Market & Competitive Intelligence

• Conduct ongoing analysis of market trends, competitive dynamics, and regulatory shifts to proactively adjust strategic priorities.
• Use data-driven insights to support strategic decision-making and scenario planning.

Leadership & Communication

• Collaborate closely with the CEO and executive team to guide key decisions and initiatives.
• Communicate strategy and performance metrics to stakeholders, including board members, leadership teams, and staff.

Qualifications & Requirements

• Bachelor's degree in Finance, Accounting, Economics, Business, or a related field (MBA or CPA preferred).
• 10+ years of progressive leadership experience in strategy, corporate finance, financial planning & analysis, or management consulting, ideally within insurance or financial services.
• Demonstrated experience leading finance transformation, improving financial systems and controls, and driving operational excellence.
• Strong understanding of financial modeling, budgeting, forecasting, and capital planning. Strategic mindset with the ability to translate complex issues into clear plans and decisions.
• Exceptional communication, collaboration, and leadership skills.

What We Offer

• The opportunity to shape the future direction of a respected, high-integrity insurance agency.
• Direct partnership with the CEO and executive team on agency-wide initiatives.
• A key role in modernizing and elevating the finance function to support future growth. Competitive compensation, including base salary, bonus potential, and benefits.
• A values-driven culture that encourages innovation, accountability, and long-term impact.

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