Sentry earned an A+ rating for the 34th consecutive year.
You’re not just in it to win it. You want to crush it every time. Because that’s what our sales professionals do. Not just anyone has what it takes to build strong and profitable relationships. If you’re a unique performer, Sentry offers a career opportunity that soars beyond commercial insurance sales.
We provide everything you need to carve out a sales career filled with success and purpose, including:
Total currently estimated projected compensation range for this position is $160,302-$196,302, which is a combination of base pay, currently projected renewal commissions, and currently estimated new business commission opportunities. Commission opportunities – both renewal and new business -- are based on achievement of sales objectives and compliance with the terms of the applicable incentive plan.
The Wisconsin territory includes: SE Wisconsin to include the Milwaukee South Metro. Residence within the sales territory is required.
What You’ll Do
What it Takes
What You’ll Receive
At Sentry, your total rewards go beyond competitive compensation. Below are some benefits and perks that you’ll receive.
About Sentry
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!
Kristina Forbes
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.
Our commitment to creating a positive, people-first culture hasn’t gone unnoticed. We’re proud to be recognized for our outstanding workplace culture.
Sentry earned an A+ rating for the 34th consecutive year.

Recognized as one of America’s Greatest Workplaces for Diversity by Newsweek.

Ranked 13th among Wisconsin’s largest private companies by revenue and impact by Deloitte.
Sentry is one of America’s Best Midsize Employers, according to Forbes.

For the second year in a row, Newsweek named Sentry one of America’s Greatest Workplaces for Women.
Forbes names Sentry as one of the Best Employers for new Grads.