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Regional Executive


At Sentry, our business is built around people.  So, we're passionate about offering the best services to our customers-and that spark begins with our team.  We are looking for a results-driven individual to lead Sentry’s Regional Business unit’s commercial lines expansion into the Northwest.  This position will be responsible for revenue and profitability of the Northwest region, most likely based in the greater Portland, Oregon area.  This executive level position will also drive selection and management of underwriting & marketing staff as well as independent agency appointments in this new Regional office. This position will report directly to the national President of the Regional business segment.

What You'll Do

As the Regional Executive, you’ll direct the positioning of Sentry’s commercial insurance products to drive premium growth, profit, and market share.  This business segment is focused on ‘full-touch underwriting’ of commercial lines with select group of appointed agents.  In addition, you’ll:
• Find motivation in building our independent agency business from the ground up in this new territory
• Set strategies using regional knowledge based on a deep understanding of market dynamics, independent agencies, and local talent within the Northwest region
• Maintain knowledge of market trends, competitors’ products, and strategies
• Create and execute business plans in the Northwest region and ensure independent agencies and staff deliver on marketing strategies and production/profit goals
• Maintain close contact with corporate marketing and underwriting functions to define target market segments, marketing requirements, and key business strategies


What it Takes

• Bachelors Degree required
• 10+ years of previous field management experience specifically within standard commercial lines property and casualty insurance
• Significant experience in commercial lines underwriting, preferably with CPCU & CIC designations
• Exceptional communication, organization, analytical, and leadership skills
• Knowledge of marketing techniques, trends, and concepts
• Deep knowledge of the Northwest marketplace, independent agencies and local talent
• Ability to meet travel requirements of the position


What You'll Receive

There is a reason why Sentry made Forbes’ list of America’s Best Midsize Employers in 2017 and 2018. At Sentry, we recognize there are many factors that contribute to your overall satisfaction both at work, and in your personal life. So, we provide a perfect mixture of compensation, benefits, company culture, and resources to ensure your everyday happiness. Below are some benefits that you’ll receive.

  • Competitive compensation to reward you for your hard work every day.
  • Generous Paid-Time Off Plan for you to enjoy time out of the office.
  • 401(K) plan with a dollar for dollar match on your first eight percent, plus immediate vesting to help fund your future. 
  • Group Medical, Dental, Vision and Life insurance to encourage a healthy lifestyle.
  • Pretax Dependent Care and Health Expense Reimbursement Accounts to ease taxes on health spending.
  • Extensive Work-Life Resources to lend a helping hand.
  • Volunteer Time Off so you can dedicate time to the community.
  • Sentry Foundation gift matching program to encourage charitable giving.

How You’ll Apply

If you are interested in joining Sentry’s team, select the one position that you are most interested in being considered for and complete your online application details. If you have applied with us before, you will only need to provide your email address and password. If this is your first time applying, you’ll need to create an account. Please upload your resume directly, in addition to completing your online application details.

Who You’ll Want to Contact

Apryl Marti at 6186551707

About Sentry

All of us at Sentry—more than 4,000 associates—have various talents, skills, and backgrounds. We work together to deliver on our promises to our policyholders every day. We’re proud to offer a full line of property, casualty, and life insurance products to help protect businesses, cars, homes, lives, and retirement income.


Our headquarters is in Stevens Point, Wisconsin, with claims and service offices located throughout the United States. From sales to claims, and information technology to marketing, we enjoy a rewarding and challenging work environment with opportunities for ongoing professional development and growth.


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.

Equal Employment Opportunity

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.


Job Title:
Regional Executive
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