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President & CEO

Job in Southborough, Worcester County, Massachusetts, 01772, USA
Listing for: Hospitality Insurance Group
Full Time position
Listed on 2026-01-29
Job specializations:
  • Management
    CFO, Operations Manager, Risk Manager/Analyst, Program / Project Manager
Job Description & How to Apply Below

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…
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