Get more out of your search

Customize your job recommendations. Get email updates when new jobs open. Upload your resume and apply again quickly and easily.

Back to Search Results

Retirement Plan Sales Executive


Sentry is looking for a high performing and driven sales professional to join our 401(k)/Retirement Plan sales force. You must be skilled at building strong and profitable relationships in defined markets.  As a Retirement Plan Sales Executive, you’ll market our 401(k) and Retirement Plans to a unique target market.  Focusing on providing services to help companies build well rounded retirement plan options for their employees.  

Sentry offers everything you need to carve out a Sales career filled with success and purpose including:

  • High earning potential plus a variety of monthly and annual incentives.
  • Outstanding benefits and a 401(k)-program matching dollar for dollar up to 8%
  • Opportunities for professional development and growth
  • Outstanding training and support
  • An industry-leading line of products and services

Bring your unique 401k Sales knowledge and experience to an unusually robust market. The territory is all of Wisconsin.  Join us!

What You'll Do

  • Sell directly to target markets that are uniquely fit the retirement plan’s focus market. 
  • Retain profitable business by providing effective, quality service to Plan Sponsors.
  • Build and maintain quality relationships with target businesses

What it Takes

  • 3-5  years experience in 401k sales
  • Exceptional sales and relationship building skills
  • A self-disciplined individual that can thrive in a remote work environment
  • Ability to multitask, prioritize, communicate effectively and remain organized
  • Bachelor’s degree or equivalent work experience
  • Acceptable Motor Vehicle Record with a valid driver’s license and ability to meet travel requirements
  • Required to have primary residence within the State of Wisconsin
  • Life License Required or ability to obtain within 90 days
  • FINRA Licenses and Retirement Plan Industry specific designations a plus

What You'll Receive

There is a reason why Sentry made Forbes’ list of America’s Best Midsize Employers in 2017. 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 - with base salary, commissions and a generous monthly and annual bonus plan.
  • Company Car with gas card
  • Group Medical, Dental, Vision and Life Insurance Benefits
  • 401 (K) plan with a dollar-for-dollar match on your first eight percent, plus immediate vesting to help fund your future
  • Laptop, cell phone reimbursement, home office setup and more!
  • Pretax Dependent Care and Health Expense Reimbursement Accounts
  • Comprehensive training, including licensure and ongoing training
  • 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 complete your application and upload your resume online.

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.

Talent Acquisition Specialist

Thank you for your interest in Sentry!

Amy Lang

Job Title:
Retirement Plan Sales Executive
Job ID:
Full/Part Time:
Share this job posting with a friend

Get more out of your search
  • See customized job recommendations
  • Get email updates when new jobs open
  • Save jobs to quickly find them later
  • Apply again quickly and easily
Related Jobs