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Sentry Jobs in Wisconsin (NOW HIRING)

Sentry Insurance

Retirement Plan Analyst

Madison, WI · On-site

For this position, Sentry does not offer employment to holders of F-1, J-1, and H-1 Visas. What You'll Do As a Senior Retirement Plan Analyst , you'll leverage your technical retirement plan ...

Sentry Insurance

Retirement Plan Analyst

Madison, WI · On-site

For this position, Sentry does not offer employment to holders of F-1, J-1, and H-1 Visas. What You'll Do As a Senior Retirement Plan Analyst, you'll leverage your technical retirement plan knowledge ...

Sentry Insurance

Barista

Stevens Point, WI · On-site

$14.75 - $17/hr

Adhere to Sentry Services health, safety, and sanitation procedures when conducting all tasks. What it Takes * Age requirement of 18+ * Strong listening, communication and customer service skills

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$13

$17

$21

How much do sentry jobs pay per hour?

As of Sep 5, 2026, the average hourly pay for sentry in Wisconsin is $17.94, according to ZipRecruiter salary data. Most workers in this role earn between $16.49 and $18.94 per hour, depending on experience, location, and employer.

What is a sentry?

Sentries are professionals responsible for monitoring and guarding a specific area, property, or facility to ensure its security and safety. Their duties often include observing for suspicious activity, checking credentials, and responding to emergencies or security breaches. Sentries may work in various environments, such as military bases, private companies, or public spaces, and often act as the first line of defense against unauthorized access.

What are the key skills and qualifications needed to thrive as a sentry, and why are they important?

To thrive as a Sentry, strong observational skills, situational awareness, and a basic education or security certification are typically required. Familiarity with surveillance systems, communication devices, and access control technologies is important for effective monitoring. Reliability, alertness, and clear communication are essential soft skills for responding to incidents and reporting concerns. These skills ensure safety, quick response to threats, and efficient security operations.

How does a sentry typically coordinate with other security personnel during an emergency situation?

During an emergency, a Sentry works closely with other security team members by maintaining clear communication through radios or designated channels. They are often responsible for monitoring entry points, relaying real-time information, and following established protocols to ensure a swift and organized response. Teamwork is essential, as Sentries may need to direct people, coordinate with supervisors, and assist law enforcement or emergency responders. Effective collaboration helps ensure safety and minimize risks during critical incidents.

What is the difference between Sentry vs Security Guard?

AspectSentrySecurity Guard
CredentialsMay require security licenses or certificationsTypically requires security guard license or certification
Work EnvironmentMonitoring premises, access control, surveillancePatrolling, guarding property, responding to incidents
Employer & IndustryBusinesses, events, facilities needing securityCommercial, residential, industrial security services
Search & Comparison IntentSecurity roles, security job descriptionsSecurity guard jobs, security employment

Both Sentry and Security Guard roles focus on safety and security, but Sentry often emphasizes surveillance and monitoring, while Security Guards may involve physical patrols and incident response. The choice depends on the specific security needs of the employer and the required credentials.

Is Sentry a good company to work for?

Sentry is a software company known for its error tracking and monitoring tools, and many employees appreciate its collaborative environment and focus on innovation. As a company, it offers roles that often require technical skills such as coding and familiarity with cloud platforms, with a generally positive reputation for work culture. However, individual experiences may vary based on role and team dynamics.

Is Sentry a remote company?

Sentry, the company behind the Sentry error tracking tool, offers many of its roles as remote positions, allowing employees to work from various locations. The company supports a flexible work environment, and remote work is common for roles involving software development, engineering, and support functions.

What are popular job titles related to Sentry jobs in Wisconsin?

For Sentry jobs in Wisconsin, the most frequently searched job titles are:

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

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

What cities in Wisconsin are hiring for Sentry jobs?

Cities in Wisconsin with the most Sentry job openings:

Sentry jobs near you
Infographic showing various Sentry job openings in Wisconsin as of August 2026, with employment types broken down into 96% Full Time, and 4% Part Time. Highlights an 98% Physical, and 2% Remote job distribution, with an average salary of $37,306 per year, or $17.9 per hour.

Director of Casualty Claims - Commercial Lines

Sentry Insurance

Stevens Point, WI • Hybrid

Full-time

Medical, Dental, Vision, Retirement, PTO

Posted 5 days ago

Sentry Insurance rating

8.7

Company rating: 8.7 out of 10

Based on 46 frontline employees who took The Breakroom Quiz

72nd of 315 rated insurance

Job description

Lead claims associates to drive compliant, timely resolutions, expense control, and superior customer service. Govern settlement authority and direct staff training.

What You’ll Do:

As the Director of Casualty Claims - Commercial Lines, you’ll serve as a leader of leaders, providing strategic and operational direction to a large team of leaders and claim associates within our casualty claim environment. In this critical role, you will drive comprehensive claim strategies for complex exposures—including Commercial Auto, Transportation Trucking, General Liability (premises and product liability), and other commercial liability scenarios—with a sharp focus on bodily injury evaluation, effective negotiation and settlement, and robust litigation strategies to serve and defend our policyholders. In addition, you will…

  • Lead and Develop Leaders: Provide strategic oversight and mentorship to your management team, fostering a high-performing culture centered on continuous learning, accountability, and the ongoing upskilling of technical proficiency across diverse claim scenarios.

  • Guide Financial and Technical Outcomes: Navigate complex authority reserving requests and provide expert settlement and negotiation guidance, ensuring equitable, timely, and compliant resolution of claims while managing expenses to support profit and growth objectives.

  • Drive Strategic and Regulatory Compliance: Spearhead strategic initiatives related to claim operations, regulatory compliance, and internal best practices, establishing robust management controls, audit standards, and protocols to achieve departmental objectives.

  • Optimize Workflows with Technology: Continually evaluate and identify opportunities to streamline claim workflows and processes utilizing technology-enabled solutions to drive operational efficiency and modernization.

  • Shape Policy and Systems: Collaborate on objective setting, the development of claims policies, and the implementation of necessary systems to support seamless claim handling and adherence to departmental standards.

  • Oversee Audits and Governance: Oversee department and corporate audits by managing communications, supplying requested data, providing supporting documentation, and addressing audit findings to ensure successful completion.

  • Represent Sentry Externally: Act as a brand ambassador, representing the company in industry associations, committees, boards, and bureaus.

What it Takes:

  • Bachelor’s degree or equivalent work experience, Juris Doctor preferred

  • 8+ years of related work experience, with successful and increasingly responsible management and leadership experience, including broad background in claims, including exposure to multiple lines of coverage and policies, preferably in commercial auto, transportation, and general liability

  • Strong analytical, communication, and human relations skills

  • Knowledge of Sentry's philosophies, products, and systems

  • Technical expertise in assigned area of claim policies and practices as well as insurance products

  • Knowledge of applicable laws affecting claims; preferably technical expertise

  • Strong working knowledge of contracts, service level agreements, and application of terms and conditions

  • Strong negotiation skills

Here is what you can look forward to as part of our team:

At Sentry, your total rewards go beyond competitive compensation. We’re committed to supporting the whole you, which is why we offer a comprehensive package designed to help you thrive both professionally and personally.

  • Hybrid Flexibility: Enjoy the best of both worlds. With optional work from home on Mondays and Fridays and join your team in the office Tuesday through Thursday to collaborate and learn. We provide the technology and tools you need for both your office and home workspace from day one.

  • Dining on Us: Depending on your location, we may provide a stipend that can be used at our on-site cafeteria or a meal allowance to keep you fueled.

  • Continuous Learning: Unlock your potential through Sentry University and take advantage of our tuition reimbursement program.

  • Comprehensive Benefits: We support your whole self with group medical, dental, and vision insurance along with parental leave, pet insurance, caregiver leave, and wellness resources. Options for HSA, FSA, and Dependent Care FSA are available.

  • Work-Life Balance: Enjoy your generous Paid Time Off allowance to rest and take advantage of paid Volunteer Time Off to support your community.

  • Investing in Your Future: We’re committed to your long-term financial well-being. We offer a 100% company match on the first 8% you contribute to your 401(k) each pay period, and those funds vest immediately.

  • Giving Back: Through the Sentry Foundation, we’re proud to support the United Way and make a difference in our communities.

Why Join Sentry?

At Sentry, we believe our people are the heart of our success. We’re proud to be recognized for the culture we’ve built, earning spots on Forbes’ lists for America’s Best Midsize Employers and Best Employers for New Grads, as well as Newsweek’s America’s Greatest Workplaces for Women and Diversity. These honors reflect our commitment to your professional satisfaction and growth.

Building on a Legacy

Our future is bright, but it’s anchored in a long history of stability. Since our founding in 1904, we’ve dedicated ourselves to helping businesses protect their futures. That trust has made us one of the largest and most financially stable mutual insurance companies in the U.S. We’re proud to have maintained an A+ rating from A.M. Best, the industry’s leading authority, for over 30 years.

Your Career, Our Community

Whether you’re working at our headquarters in Stevens Point, Wisconsin, or one of our many offices across the country, you’ll find a challenging and rewarding environment. Explore the Our Teams tab on our Career Page to see the diverse career paths we offer, with a focus on ongoing development and professional growth.

Ready to own your future? Join us at Sentry, opportunities await!

Joe Larsen

Senior Talent Acquisition Specialist

Joe.Larsen@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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