President & CEO - Southborough, MA

About the Company · Hospitality Insurance Group ("HIG") is a niche property and casualty insurance company headquartered in Southborough, Massachusetts. With approximately $21 million in direct written premium, HIG specializes in providing insurance solutions to the hospitality i ...

Job description

About the Company

Hospitality Insurance Group ("HIG") is a niche property and casualty insurance company headquartered in Southborough, Massachusetts. With approximately $21 million in direct written premium, HIG specializes in providing insurance solutions to the hospitality industry, including restaurants, bars, taverns, social clubs, caterers, small music venues, liquor stores, convenience stores, and other main-street businesses. Formed from the Massachusetts Liquor Liability Joint Underwriting Association, HIG has evolved into a multi-state writer licensed in seven states across the Northeast and Mid-Atlantic. Following a 2025 reorganization and $5.5 million capital infusion, HIG is positioned for long-term profitable growth supported by a strong surplus base, enhanced technology, and deep expertise in hospitality-related risks.

Mission & Strategic Context

HIG's mission is to provide outstanding insurance coverage to hospitality businesses, promote responsible alcohol service, and deliver financial strength and stability to policyholders. Over the next decade, HIG seeks to achieve consistent underwriting profitability, responsible premium growth, and recognition as a leading niche insurer in the Eastern United States. The company's strategic plan emphasizes disciplined underwriting and rate adequacy across all lines, expansion of product offerings (including BOP, brewery, and potential non-admitted products), geographic diversification, enhanced data analytics and automation, robust enterprise risk management, capital strength, and strong partnerships with agents and associations.

About the Role

The President & Chief Executive Officer (CEO) is the chief executive of HIG and is accountable to the Board of Directors for the overall leadership, management, and performance of the company. The CEO sets the strategic direction, drives financial and operational results, ensures regulatory compliance and effective governance, and maintains HIG's culture of professionalism, integrity, and customer focus. The CEO must combine strategic foresight, financial acumen, and operational discipline with the ability to inspire a small, highly skilled team and represent HIG credibly with regulators, reinsurers, agents, and industry partners.

Responsibilities

Strategic Leadership

• Lead the formulation, communication, and execution of HIG's strategic plan.
• Ensure strategies align with the company's mission, capital capacity, and risk appetite.
• Anticipate market shifts—including soft-market cycles—and position HIG for sustained profitability and growth.
• Pursue diversification within the hospitality sector and expansion into adjacent markets consistent with the plan's phased growth model.
• Champion innovation through data analytics, automation, and use of technology to enhance decision-making and efficiency.

Financial & Operational Management

• Drive performance to achieve planned results for net income, surplus growth, and underwriting profitability.
• Oversee the integrity of financial statements, budgets, and forecasts.
• Manage capital prudently, ensuring adequate reserves and strong RBC ratios.
• Direct reinsurance strategy and expense management to optimize value.
• Monitor operational efficiency through productivity, process audits, and cost-benefit analysis of vendor relationships.

Risk Management & Compliance

• Maintain a robust enterprise risk management program that identifies and mitigates key risks.
• Ensure compliance with all insurance laws, regulations, and corporate governance standards.
• Oversee cybersecurity strategy, ensuring defenses, employee training, and contingency plans are current.
• Cultivate positive relationships with regulators in all jurisdictions and ensure transparency in filings and communications.
• Prepare the company to navigate market softening through disciplined underwriting and data-driven pricing.

Business Development & Market Expansion

• Strengthen agency distribution by expanding productive agency relationships and appointments.
• Foster partnerships with hospitality and restaurant associations and leverage HIG's admitted-carrier advantage.
• Oversee product innovation and development of non-admitted capabilities and niche products.
• Support marketing and branding initiatives to enhance awareness of HIG beyond liquor liability.
• Represent HIG externally with integrity and authority, serving as its public face to the market.

Leadership & Organizational Development

• Lead, mentor, and develop a small but experienced management team, promoting collaboration and accountability.
• Foster a culture of performance, empowerment, and professional growth.
• Ensure the company's organizational structure and staffing levels are aligned with growth objectives.
• Promote equal opportunity within the workforce.

Governance & Board Relations

• Partner effectively with the Board to establish goals, strategies, and policies.
• Provide timely, accurate, and insightful reports and recommendations.
• Execute the Board's directives with transparency and accountability.
• Keep the Board informed of material risks, opportunities, and developments.

Performance Metrics

The Board of Directors will evaluate the CEO based on performance against the following measures:

• Financial outcomes: profitability, combined ratio, surplus growth, and expense ratio improvement.
• Strategic execution: progress on product diversification, state expansion, and technology modernization.
• Capital and risk management: maintenance of strong RBC and reserve ratios, and sound reinsurance program.
• Leadership and succession: development and retention of key staff and organizational alignment.
• Governance and relationships: quality of Board communication, regulatory standing, and stakeholder confidence.
• Brand and market presence: enhanced recognition as a niche hospitality insurer and preferred partner for agents and associations.

Qualifications

• Bachelor's degree required; advanced degree (MBA, JD, or CPCU/ARM designation) preferred.
• Minimum 10–15 years of progressive leadership in property and casualty insurance, with experience in underwriting, operations, or finance.
• Demonstrated success leading a regulated insurer or equivalent business unit with P&L accountability.
• Experience managing relationships with regulators, rating agencies, and reinsurers.
• Proven ability to execute profitable growth strategies in a specialty or niche market.
• Familiarity with hospitality-related risks or small commercial business preferred.
• Demonstrated skill in building and motivating small, high-performing teams.

Leadership Competencies

• Strategic Vision & Execution: balances innovation with disciplined growth.
• Financial Acumen: interprets complex data and drives sound financial decisions.
• Integrity & Accountability: models ethical conduct and transparency.
• Operational Excellence: builds efficient systems and measures performance rigorously.
• Collaborative Leadership: develops people and fosters teamwork.
• Change Management: embraces modernization and leads through transition.
• Stakeholder Engagement: maintains credibility and trust with Board, regulators, agents, and policyholders.

Location & Travel

Based in Southborough, Massachusetts, with travel throughout HIG's seven-state footprint and occasional attendance at industry and regulatory meetings.

Compensation

Competitive compensation package commensurate with experience, including base salary, performance incentives aligned with company objectives, and benefits as determined by the Board of Directors.