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Sentry Insurance Jobs in Wisconsin (NOW HIRING)

Sentry Insurance

Associate SEM Analyst

Madison, WI

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 ...

Sentry Insurance

Associate SEM Analyst

Madison, WI · On-site

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 ...

Sentry Insurance

Internal Auditor

Stevens Point, WI

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 ...

Sentry Insurance

Retirement Plan Analyst

Madison, WI

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 ...

Sentry Insurance

Retirement Plan Analyst

Madison, WI · Hybrid

Group Medical, Dental, Vision and Life insurance to encourage a healthy lifestyle. * Extensive Work-Life Resources to lend a helping hand. * Sentry Foundation gift matching program to encourage ...

Sentry Insurance

Premium Audit Technician

Stevens Point, WI · On-site

$48K - $58K/yr

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 ...

Sentry Insurance

Payroll Analyst

Stevens Point, WI

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 ...

Sentry Insurance

Internal Auditor

Stevens Point, WI · On-site

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 ...

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Showing results 21-40

All JobsSentry Insurance JobsSentry Insurance Jobs in Wisconsin

Sentry Insurance information

See Wisconsin salary details

$31.3K

$66.5K

$83.8K

How much do sentry insurance jobs pay per year?

As of Aug 19, 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.

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 the key skills and qualifications needed to thrive as an insurance agent at Sentry Insurance?

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 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.

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.

Is Sentry Insurance a good company to work for?

Sentry Insurance is generally regarded as a stable employer with a focus on employee benefits and a collaborative work environment. Employees often cite opportunities for professional development and a positive company culture, though experiences can vary by role and location.

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 job categories do people searching Sentry Insurance jobs in Wisconsin look for?

The top searched job categories for Sentry Insurance jobs in Wisconsin are:

What cities in Wisconsin are hiring for Sentry Insurance jobs?

Cities in Wisconsin with the most Sentry Insurance job openings:

Sentry Insurance jobs near you
Infographic showing various Sentry Insurance job openings in Wisconsin as of August 2026, with employment types broken down into 1% As Needed, 76% Full Time, 19% Part Time, and 4% Contract. Highlights an 89% Physical, 1% Hybrid, and 10% Remote job distribution, with an average salary of $66,464 per year, or $32 per hour.

Software Engineer (Hybrid Work Model)

Sentry Insurance

Stevens Point, WI • Hybrid

Full-time

Retirement, PTO

Re-posted 23 days ago

Sentry Insurance rating

8.7

Company rating: 8.7 out of 10

Based on 46 frontline employees who took The Breakroom Quiz

71st of 310 rated insurance

Job description

At Sentry, we’re more than just insurance—and we can offer you more than just a job. We want you to enjoy a career with us, where you’re in the driver’s seat of your career path with access to resources to help you succeed personally and professionally.
As a member of the Digital and Web Services team, you will develop applications and websites that deliver exceptional user experiences for our customers. This position can be filled as a Software Developer or a Software Engineer, based on the qualifications and experience of the selected candidate.

What You’ll Do

You’ll be a valuable contributor to our team. As a Sentry associate, we believe in your skills and knowledge. Your input and participation matters. You’ll have the opportunity to:

  • Innovate: Through our agile development process, you’ll have the opportunity to apply your creativity and innovation to drive new solutions.

  • Learn: Sentry provides several resources to help you further your career and continue your personal development, including Sentry University, LinkedIn Learning, and peer-led educational sessions and communities.

  • Grow: Sentry provides many opportunities to grow in your career. Through meaningful, ongoing conversations around growth and development, we encourage all associates to take ownership in their career path.

  • Contribute: You’ll work in a full-stack, cloud-first, development environment where you'll have the chance to work in many industry-leading technologies, including: Java, Angular, VueJs, Swift, Kotlin, and many more. As a Software Developer, you will:

    • Engage in the design, development, and implementation of new and existing java programs or solutions.

    • Actively engage in team delivery functions such as design reviews, code reviews, and scrum meetings.

    • Demonstrate ownership over the quality of solutions through monitoring production health, resolving defects, and ensuring production stability.

  • What it Takes:

    • Associate Degree in Computer Science or related discipline. Bachelor Degree preferred.

    • Demonstrated aptitude on one or more programming languages and software development concepts.

If you have experience or knowledge in the skills listed above, please consider joining our Sentry team!

What You’ll Receive

You can enjoy a complete benefits package, including generous paid time off, 8% 401(k) match, matching charitable gift program, bonus plan based on company performance, meal stipends, associate discounts, volunteer time off and more!

You want a positive work/life balance. Our hybrid work model allows you to enjoy the benefits of working from home on Monday and Friday, but also provides the opportunity for team building and collaboration when working in the office on Tuesday, Wednesday, and Thursday. To help you work effectively and comfortably in both locations, we provide you with equipment to work at home and in the office.

About Sentry

Our Background: We’re part of one of the largest and most financially secure mutual insurance groups in the nation. We’ve earned an A+ rating from AM Best every year since 1992. Our associates bring together diverse backgrounds, experiences, and skillsets to make Sentry who we are. We’re honored to earn a spot on Forbes list of America's Best Midsize Employers, joining a select group of 400 companies. We’re in the business of helping others, and that includes the communities where we live and work. Our annual United Way campaign has raised more than $1 million for the past several years.

How You’ll Apply

We’d love for you to join us. Please complete your online application and upload your resume on our Careers site. If you have applied with us before, you only need to provide your email address and password. If this is your first time applying with Sentry, please create an account.

If you have specific questions regarding the position, application process, or are interested in learning more about Sentry, please reach out to Katelynne Rivera, Talent Acquisition Specialist Sr.

For this position, Sentry does not offer employment to holders of F-1, J-1, and H-1 Visas.

Get ready to own your future at Sentry. Your opportunity awaits.

Talent Acquisition Specialist

Thank you for your interest in Sentry!

Katelynne Rivera

Katelynne.Rivera@Sentry.com

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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