Chief of Staff to the CEO

About Us

At Selective, we don't just insure uniquely, we employ uniqueness.

Selective is a midsized U.S. domestic property and casualty insurance company with a history of strong, consistent financial performance for nearly 100 years. Selective's unique position as both a leading insurance group and an employer of choice is recognized in a wide variety of awards and honors, including listing in Forbes Best Midsize Employers in 2025 and certification as a Great Place to Work® in 2025 for the sixth consecutive year.

Employees are empowered and encouraged to Be Uniquely You by being their true, unique selves and contributing their diverse talents, experiences, and perspectives to our shared success. Together, we are a high-performing team working to serve our customers responsibly by helping to mitigate loss, keep them safe, and restore their lives and businesses after an insured loss occurs.


Overview

Selective Insurance is recruiting for a Chief of Staff to the CEO. This is a senior enterprise-level leader who serves as a strategic advisor, integrator, and force-multiplier for the CEO and, by extension, the Executive Leadership Team (ELT). This role enhances organizational effectiveness by advancing enterprise priorities, shaping strategic planning and execution, and ensuring disciplined follow-through on the company's most critical priorities.


This position is intentionally strategy and business-forward, with a strong focus on enterprise alignment, operating cadence, and execution of strategic priorities and high-impact initiatives that cut across the organization. The Chief of Staff translates strategic direction into actionable plans, bringing structure, rigor, and accountability to enterprise objectives while enabling the organization to move forward in alignment with focus, clarity, and accountability.


All job duties and responsibilities must be carried out in compliance with applicable legal and regulatory requirements.


Responsibilities

• Enterprise Strategy: Partner with the CEO and executive team to shape enterprise strategy, facilitate the strategic planning cycle, and translate key priorities into focused initiatives, execution plans, success measures, and aligned executive messaging and decision-making.
• Enterprise Operational Alignment, Execution, and Efficiency: Establish and maintain an enterprise operating cadence that drives alignment, decision quality, accountability, and disciplined execution across divisions, business units, and functional areas. Partner with senior leaders to align objectives, plans, resources, and performance measures; proactively elevate risks and interdependencies; and lead cross-functional initiatives that advance enterprise priorities and measurable outcomes.
• Enterprise Performance & Insight: Define and maintain enterprise tracking mechanisms, dashboards, and scorecards that monitor progress, risks, and outcomes across strategic initiatives and provide actionable insights to inform CEO and ELT decision-making.
• Executive Enablement & Communications: Serve as a strategic extension of the CEO by synthesizing insights, preparing high-quality materials and messaging, managing executive and business review forums, and ensuring key priorities, decisions, and commitments are clearly communicated and advanced across the enterprise.
• Leadership & Influence: Build trust-based relationships with senior leaders and serve as a neutral enterprise integrator who influences without direct authority, models sound judgment and discretion, and drives alignment, action, and outcomes.

Qualifications

Knowledge and Requirements

• Executive level role with significant leadership, independence and judgement.
• Broad enterprise impact across functions and strategic priorities.
• Expected to act with executive level judgement, context, and enterprise mindset.

Experience and Education

• 10+ years progressive experience in strategy, consulting, enterprise operations, or senior leadership advisory roles supporting C-suite leaders, Boards, executive leadership teams, and enterprise-wide initiatives with measurable business outcomes preferably in the P&C industry.
• Bachelor's Degree in Business, Management, Finance, Strategy or related field required.
• MBA or other advanced degree preferred.

Total Rewards

Selective Insurance offers a total rewards package that includes a competitive base salary, incentive plan eligibility at all levels, and a wide array of benefits designed to help you and your family stay healthy, achieve your financial goals, and balance the demands of your work and personal life. These benefits include comprehensive health care plans, retirement savings plan with company match, discounted Employee Stock Purchase Program, tuition assistance and reimbursement programs, and 20 days of paid time off. Additional details about our total rewards package can be found by visiting our benefits page.

The actual base salary is based on geographic location, and the range is representative of salaries for this role throughout Selective's footprint. Additional considerations include relevant education, qualifications, experience, skills, performance, and business needs.


Pay Range

USD $300,000.00 - USD $350,000.00 /Yr.
Additional Information

Selective is an Equal Employment Opportunity employer. That means we respect and value every individual's unique opinions, beliefs, abilities, and perspectives. We are committed to promoting a welcoming culture that celebrates diverse talent, individual identity, different points of view and experiences - and empowers employees to contribute new ideas that support our continued and growing success. Building a highly engaged team is one of our core strategic imperatives, which we believe is enhanced by diversity, equity, and inclusion. We expect and encourage all employees and all of our business partners to embrace, practice, and monitor the attitudes, values, and goals of acceptance; address biases; and foster diversity of viewpoints and opinions.

For Massachusetts Applicants

It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.