We're passionate about offering the best services to our customers-and that spark begins with our team.  This position will be responsible for revenue and profitability of the Hawaii region, with the ideal candidate residing on the island of Oahu. 

What You'll Do

As an Underwriting Leader you will independently build, manage, and provide ownership to a new book of business. In addition, you will:

• Direct the positioning of Sentry’s products to increase premium, profit, and market share.
• Create and execute an effective business strategy to optimize premium growth and profitability across lines of business.
• Maintain knowledge of market trends, competitor products and strategies, rate levels, and product success and shortcomings in order to reach profitable growth objectives.
• Set strategies using commercial lines business knowledge based on a deep understanding of market dynamics, independent agencies, and local talent within the area to build and manage a profitable book of business.
• Plan and conduct account and agency meetings, seeking and assisting with the appointment of new agents.
• Solicit accounts through appointed commercial lines independent agents.
• Analyze quality and quantity of risks underwritten and evaluate prospective accounts and independent agencies to determine their acceptability of the risks and services needed.
• Monitor, review, and evaluate results, premium trends and retention, new business and loss ratio of assigned territory.
• Be responsible for building and leading a small team of underwriters, including performance oversight and professional growth to achieve business unit goals and maintain high performance standards

What it Takes 

• 10+ years of underwriting experience specifically within standard commercial lines property and casualty insurance in the state of Hawaii
• Familiarity with the Commercial Lines marketplace in the state of Hawaii and experience working the agents on the islands
• Experience with effectively building and managing a profitable book of commercial lines business with the ability to manage profitability through effective agency management
• Strong familiarity with state insurance regulations
• Understanding and knowledge of selecting and managing independent commercial lines agents
• Proficiency developing a strategic business plan for entry into new markets
• Experience collaborating with products and pricing teams in introducing new products or enhancements to existing products

What You'll Receive 

At Sentry, your total rewards go beyond competitive compensation. Below are some benefits and perks that you’ll receive. 

• 401(K) plan with a dollar-for-dollar match on your first eight percent, plus immediate vesting to help strengthen your financial future.  
• Generous Paid-Time Off plan for you to enjoy time out of the office as well as Volunteer-Time off  
• Group Medical, Dental, Vision, Life insurance, Parental leave, and our Health and Wellness benefits to encourage a healthy lifestyle.  
• As a Sentry associate, you will have an in-office workspace and materials for your home office. In addition to the laptop, you will receive prior to your start, Sentry will provide equipment for your home office.  
• Continue your education and career development through Sentry University (SentryU) and utilize our Tuition Reimbursement program.  
• Well-being and Employee Assistance programs. 
• Sentry Foundation gift matching program to encourage charitable giving. 
• Based on experience and qualifications, the pay range for this position as an Underwriting Leader is $170,000 - $225,000 annually.

About Sentry 

While our headquarters are in Stevens Point, Wisconsin, and we have offices across the United States, Sentry has built a strong and lasting relationship with the Maui community, the former home of the PGA TOUR's The Sentry event. Through our Connected Communities initiative, we connect organizations in Stevens Point and Maui with shared goals in education, agriculture, community service, and even brewing—fostering collaboration that benefits both communities. Additionally, Sentry has supported Maui through philanthropic partnerships with organizations including Maui United Way, Maui Food Bank, Boys & Girls Clubs of Maui, and other local nonprofits; disaster relief following the Lahaina wildfires; and the Sentry Scholars program, which provides scholarships to Maui students.

We take great pride in making Forbes’ list of America’s Best Midsize Employers. A lot of different factors go into that honor, many of which contribute to your job satisfaction.  

Our bright future is built on a long-track record of success. We got our start in 1904 and have been helping businesses succeed and protect their futures ever since. Because of the trust placed in us, we’re one of the largest and financially strongest mutual insurance companies in the United States. We’re rated A+ by A.M. Best, the industry's leading rating authority. 

Get ready to own your future at Sentry. Opportunities await!  

Talent Acquisition Manager

Hannah Krueger

[email protected]

Equal Employment Opportunity

Sentry is an Equal Opportunity Employer. It is our policy that there be no discrimination in employment based on race, color, national origin, religion, sex, disability, age, marital status, or sexual orientation.