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Sentry Insurance Jobs in Wisconsin (NOW HIRING)

Line/Grill Cook

Stevens Point, WI

$15.25 - $19.25/hr

At Sentry, the best parts of our business come from our very own backyard. All across our ... Group Medical, Dental, Vision and Life  Insurance  to encourage a healthy lifestyle * 401 (K) ...

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Sentry Insurance information

See Wisconsin salary details

$31.3K

$66.5K

$83.8K

How much do sentry insurance jobs pay per year?

As of Jun 16, 2026, the average yearly pay for sentry insurance in Wisconsin is $66,464.00, according to ZipRecruiter salary data. Most workers in this role earn between $60,600.00 and $75,700.00 per year, depending on experience, location, and employer.

Is Sentry Insurance a good company?

Sentry Insurance is a well-established insurance provider known for its stability and employee benefits. The company generally receives positive reviews for its work environment and job stability, making it a reputable employer in the insurance industry.

What are the key skills and qualifications needed to thrive as an Insurance Agent at Sentry Insurance, and why are they important?

To thrive as an Insurance Agent at Sentry Insurance, you need strong sales abilities, knowledge of insurance products, relevant state licensure, and often a bachelor’s degree or equivalent experience. Familiarity with customer relationship management (CRM) software and quoting systems is typically required. Outstanding interpersonal skills, active listening, and problem-solving abilities help agents build trust and address client needs effectively. These skills are vital for meeting sales targets, ensuring customer satisfaction, and maintaining compliance in a competitive insurance market.

What is the difference between Sentry Insurance vs Claims Adjuster?

AspectSentry InsuranceClaims Adjuster
CredentialsLicenses, insurance certificationsLicenses, insurance certifications
Work EnvironmentOffice, remote, fieldOffice, remote, field
Industry UsageInsurance provider, underwritingInsurance, claims processing
Primary RoleInsurance provider, risk assessmentEvaluate and settle insurance claims

While Sentry Insurance is a provider offering various insurance products, a Claims Adjuster is a professional who evaluates insurance claims on behalf of insurers like Sentry. Claims Adjusters work directly with policyholders to assess damages and determine payouts, whereas Sentry Insurance manages the overall insurance policies and underwriting processes.

What opportunities for professional development and advancement are typically available to employees at Sentry Insurance?

At Sentry Insurance, employees often benefit from a range of professional development opportunities, including ongoing training, mentorship programs, and support for industry certifications. The company encourages internal mobility, allowing employees to explore different roles or departments based on their interests and performance. Advancement is typically based on a combination of demonstrated skills, leadership potential, and contributions to team goals. Employees are also supported through structured performance reviews and clear career pathways, helping them to grow within the organization.

Is Sentry a good company to work for?

Sentry Insurance is generally regarded as a stable employer with a focus on employee benefits and professional development. The company offers a collaborative work environment and values skills in insurance, risk management, and customer service. Employee reviews often highlight positive workplace culture and opportunities for growth.

What is the highest paid job in insurance?

In the insurance industry, executive roles such as Chief Executive Officer (CEO) or Chief Underwriting Officer tend to be the highest paid, often earning six-figure salaries plus bonuses. These positions require extensive experience, leadership skills, and industry knowledge, and may involve overseeing company strategy, risk management, and operations.

What is the highest paying insurance agent job?

The highest paying insurance agent roles are typically senior or specialized positions such as captive agents working for large insurance companies or those with extensive experience and a strong client base. These roles often offer higher commissions, bonuses, and incentives, especially for agents selling high-value or complex policies like commercial or specialty insurance. Earning potential increases with certifications, expertise, and sales performance.

What is Sentry Insurance?

Sentry Insurance is a mutual insurance company that provides a variety of insurance products, including business insurance, personal auto insurance, and life insurance. Founded in 1904 and headquartered in Stevens Point, Wisconsin, Sentry serves policyholders across the United States. The company is known for its strong financial stability and focus on customer service, offering solutions for businesses of all sizes as well as individuals seeking personal coverage.
What are popular job titles related to Sentry Insurance jobs in Wisconsin? For Sentry Insurance jobs in Wisconsin, the most frequently searched job titles are:
What cities in Wisconsin are hiring for Sentry Insurance jobs? Cities in Wisconsin with the most Sentry Insurance job openings:
Infographic showing various Sentry Insurance job openings in Wisconsin as of June 2026, with employment types broken down into 75% Full Time, and 25% Part Time. Highlights an 100% In-person job distribution, with an average salary of $66,464 per year, or $32 per hour.
Account Specialist - Davenport, IA or Stevens Point, WI

Account Specialist - Davenport, IA or Stevens Point, WI

Sentry Insurance

Stevens Point, WI

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 11 days ago


Sentry Insurance rating

8.6

Company rating: 8.6 out of 10

Based on 42 frontline employees who took The Breakroom Quiz

73rd of 261 rated insurance


Job description

As an Account Specialist with Sentry, you’ll serve as a relationship builder to customers and internal partners to develop positive relationships with assigned accounts or regions.

This role is required to work standard hours of Monday - Friday from 8 AM - 4:30 PM. This role will follow Sentry's hybrid work model and can work out of the Davenport, Iowa or Stevens Point, WI Sentry offices.

What You'll Do:

  • Serve as primary point of contact and resource for designated producer(s), customers, and/or agents within the territory.  Act as a relationship builder by using a combination of soft skills to connect with internal teams, customers and agents to form positive relationships

  • Partners with producers to service existing book and identify opportunities for partner placement agency (Parker Stevens Agency or Hortica Brokerage)

  • Makes detailed decisions, and understands business risks and consequences of them

  • Serve as primary point of contact and owner of all service-related items, such as incoming customer calls, emails, and faxes regarding service needs, changes, questions, and problems

  • Provide proactive service needs to ensure completion, including quotes, renewals, policy changes, urgent recommendations, billing, and audits

  • Creates new and renewal applications to these smaller businesses

  • Act as a relationship builder and liaison between sales producer, underwriting, other internal departments, and/or customers or agents in gathering of underwriting requirements and customer documents/signatures

What it Takes:

  • Associate degree or equivalent work experience

  • 2+ years of related work experience

  • Property & Casualty License required; if not currently licensed, must obtain within 120 days of hire

  • Prior Commercial Lines insurance experience desired with knowledge of Commercial Lines products and/or underwriting guidelines

  • Ability to interpret and apply internal practices, commercial insurance concepts and underwriting guidelines 

  • Ability to work independently and able to manage individual time among competing priorities

  • Ability to travel on a limited basis to attend team meetings and/or to meet prospects or current customers

  • Strong PC skills and ability to quickly learn a variety of software applications

  • Composure, strong customer service skills and ability to build and maintain relationships is key

  • Ability to balance multiple priorities in a fast-paced work environment and work independently with little direction

What You'll Receive:


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

Sentry is happy to offer flexibility through a scheduled Hybrid work model. Monday and Friday work from home if you choose to, Tuesday through Thursday you’ll work in office


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


Meal Subsidy available for associates who report to an office


401(K) plan with a dollar-for-dollar match on your first eight percent, plus immediate vesting to help strengthen your financial future


Continue your education and career development through Sentry University (SentryU) and utilize our Tuition Reimbursement program


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


Well-being and Employee Assistance programs 


Sentry Foundation gift matching program to encourage charitable giving

About Sentry

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.


Our headquarters is in Stevens Point, Wisconsin, with 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. 

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

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.

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.


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