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Sentry Insurance Jobs in Wisconsin (NOW HIRING)

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 ...

Print to Mail Operator I

Stevens Point, WI · On-site

$16.50 - $20/hr

This position will be located on-site at the Sentry Home Office in Stevens Point, WI and will be ... mutual insurance companies in the United States. We're rated A+ by A.M. Best, the industry ...

Sentry - 1800 North Point Drive, Stevens Point, WI 54481. Note: online applications accepted only ... Medical, Dental, Vision, Life Insurance/AD, Disability Insurance, Commuter Benefits, Employee ...

COOK

Stevens Point, WI · On-site

$18/hr

Sentry - 1800 North Point Drive, Stevens Point, WI 54481. Note: online applications accepted only ... Medical, Dental, Vision, Life Insurance/AD, Disability Insurance, Commuter Benefits, Employee ...

Sentry - 1800 North Point Drive, Stevens Point, WI 54481. Note: online applications accepted only ... Medical, Dental, Vision, Life Insurance/AD, Disability Insurance, Commuter Benefits, Employee ...

Sentry - 1800 North Point Drive, Stevens Point, WI 54481. Note: online applications accepted only ... Medical, Dental, Vision, Life Insurance/AD, Disability Insurance, Commuter Benefits, Employee ...

Stockroom Attendant

Waukesha, WI · On-site

$46K - $55K/yr

City of Waukesha -CITY GARAGE - 300 Sentry Drive Waukesha, WI Job Type: Full Time Job Number: 26 ... Insurance * Health * Dental * Life * Vision * Pension * Flexible Benefit Plan * AFLAC * Short Term ...

Mechanic

Waukesha, WI · On-site

$56K - $78K/yr

City of Waukesha -CITY GARAGE - 300 Sentry Drive Waukesha, WI Job Type: Full Time Job Number: 25 ... insure proper care and servicing. 4. Performs arc and gas welding or cutting for maintenance ...

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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.

Operations Technician Senior - Commercial Lines

Sentryinsurance

Stevens Point, WI • On-site

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 3 days ago


Job description

This position will be based out of our Stevens Point, WI office and will follow Sentry's hybrid model of 3 days in-office.

The Operations Technician Senior will support commercial lines (CL) operational and underwriting processes within guidelines by handling a variety of basic to moderately complex policy transactions that support the review and acceptance/decline of new or renewal CL business.
This team member assists on behalf of underwriting claims, sales producers, and agents, compiles and/or shares policy and coverage for assigned lines of business and customers. They will ensure proper documentation and records management according to regulatory and Sentry standards.

What You'll Do:


Provide operations support, including processing of new and renewal transactions and policy updates
Perform moderately complex operations support duties and handle production problem listings
Utilize various systems and sites to resolve and correct Workers' Compensation and Auto Liability Reporting errors
Use problem-solving skills and best judgment to work with internal business units to resolve problems and provide insight about service

Additional responsibilities include:


Requires knowledge of Sentry systems, processes and procedures
May provide testing of new or revised procedures as it relates to the business systems. May assist with procedure writing
May update the policy administration system when the business area is notified sales recodes need to occur on accounts, sales territory splits, etc. for Commercial Lines
May assist in training and quality auditing of new operation technician seniors
Refers questions outside of responsibility/authority
Performs other job-related duties as assigned from time to time

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.