Sentry
Our associates are the most important part of our company.


We became one of the most financially strong mutual insurance companies in the U.S. by striving to provide the best possible service to our business customers. We do this by having conversations, forming relationships, and getting to know the people we work with and their businesses.

We make that same commitment to our associates. When you join Sentry, we don’t just want you to perform tasks each day. We want you to enjoy your time with us. You’re in the driver’s seat of your career path here—sharing feedback, creating goals, accessing professional development resources, and identifying how you can contribute to both your success and the success of the company.

Yes, we work hard. But we work with the purpose of helping others, and with the understanding that there’s more to life than work. We invite you to learn more about us. You’ll find we’re much more than insurance.

04/20/2026  
Provides quality customer service to participants and policy owners in our 401K area. ** This role can be filled at our Stevens Point, WI Office following a hybrid work model ** What You'll Do As a Customer Service Representative – 401K & L&A you will: Ensure a quality customer experience for our participants and policy owners by reducing friction points and ensuring an effortless process. Listen to and assesses customer needs to take appropriate action to fulfill their requests. Be a key point of contact for customers, builds positive relationships and creates customer confidence, loyalty, and retention by resolving requests using knowledge, empathy, and sound judgment. Provides timely customer service meeting or exceeding specified service standards. Receives telephone calls for assigned line of business and provides upfront assistance to our participants and policy owners in need of service. These needs may include locating, providing, or obtaining...
Sentry Stevens Point, WI Full Time
04/20/2026  
You’ll provide administrative and operational support for the claims department, handling mail and data entry. You’ll assist internal customers, vendors, and technical staff. As an Associate Claims Technician - Data Administration, you'll provide basic administrative and operational support for the claims department, which includes identification and routing of mail, returning of misrouted or unidentified mail, data entry, and monitoring work queues. You'll work with internal customers, vendors, attorneys, adjusters, and others to help resolve issues and provide administrative support to technical staff.  This position will be located at our Stevens Point, WI office following the hybrid work model and is NOT available for remote work.   What You'll Do:   Scan, route, and classify incoming mail for all claims lines of business and monitor electronic queues to ensure claims staff receive appropriate materials and documents. Research incoming documents to identify...
Sentry Stevens Point, WI Full Time
04/20/2026  
Join our Commercial Auto team by leading claim investigations, assessing liability, and driving fast, fair resolutions for policyholders. This position will be located at our Stevens Point, WI office following the hybrid work model and is NOT available for remote work. What You'll Do: As an Entry Level Claims Representative, you will: Gain knowledge to verify coverage, compensability, and reasonable payments by thoroughly reviewing the policy, reviewing accident details, and other pertinent information related to the claim. Develop investigative claims skills by taking and reviewing recorded statements from involved parties and witnesses, reviewing police reports, and other pertinent evidence. Build knowledge to evaluate claims exposure appropriately, establishing timely reserves. Comply with industry regulations, legal requirements, and internal company policies through thorough documentation of all decisions, correspondence, and discussions...
Sentry Stevens Point, WI Full Time
04/20/2026  
Our highly trained Account Executives present specialized commercial insurance, 401K, and life insurance products that are perfectly designed for the industries we serve. You’re not just in it to win it. You want to crush it every time. Because that’s what our sales professionals do. Not just   anyone   has what it takes to build strong and profitable relationships. If you’re a unique performer, Sentry offers a career opportunity that soars beyond commercial insurance sales.       We provide everything you need to carve out a sales career filled with success and purpose, including:     High earning potential with base salary, commissions, monthly/annual incentives, plus recognition trips   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...
Sentry Stockton, CA Full Time
04/20/2026  
Join our detail-oriented housekeeping team that helps maintain the beauty and charm of The Inn at SentryWorld At The Inn at SentryWorld, our business is about people and the relationships we build. Our atmosphere is welcoming, and our team is genuine, dedicated and insightful when it comes delivering excellent service. The team is seeking a Full-time housekeeper to join our detail-oriented housekeeping team at The Inn at SentryWorld. This position has a starting rate of $16/hour. What You’ll Do As a housekeeper, you will: Clean guest rooms to ensure all areas are properly sanitized and appropriately stocked with room amenities. Change and replace guest room bedding and towels and direct necessary items to laundry area. Vacuum guest rooms and clean all floor surfaces while following set procedures. Dust and sanitize all in-room surfaces, safely, using appropriate chemicals and equipment. Deliver items such as extra linens, towels or pillows to rooms upon guest...
Sentry Stevens Point, WI Full Time
04/20/2026  
Join our Rapid Resolution team by leading claim investigations, assessing liability, and driving fast, fair resolutions for policyholders. This position will be located at our Madison, WI office following the hybrid work model and is NOT available for remote work. What You'll Do   As a Claims Representative Entry Level, you will:  Gain knowledge to verify coverage, compensability, and reasonable payments by thoroughly reviewing the policy, reviewing accident details, and other pertinent information related to the claim.  Develop investigative claims skills by taking and reviewing recorded statements from involved parties and witnesses, reviewing police reports, and other pertinent evidence.  Build knowledge to evaluate claims exposure appropriately, establishing timely reserves.  Comply with industry regulations, legal requirements, and internal company policies through thorough documentation of all decisions, correspondence, and discussions that occur...
Sentry Madison, WI Full Time
04/17/2026  
The Inn at SentryWorld is about people and the relationships we build. Our onsite Baristas not only craft wonderful beverages for our guests, but they also create an experience. Based on availability and business needs, this position could be filled as part-time or full-time What You’ll Do As a barista at the Library Café, you will: Greet customers and engage in conversations regarding available food and beverage items, and current specials. Process orders ensuring all transactions are handled timely and accurately.  Prepare and/or serve bakery and beverages, such as coffee, espresso, and tea according to company standards and customer requests. Clean and organize work and storage areas including, but not limited to equipment, cases, dishes, counters, refrigerators, and floors to ensure a sanitary work environment and easy access to needed resources. Monitor equipment to ensure it is operating properly and report any maintenance needs. Perform...
Sentry Stevens Point, WI Full Time
04/17/2026  
SentryWorld PJ’s is seeking an energetic and enthusiastic Host/Hostess. As a host you would be responsible for greeting, welcoming and seating all guests on a timely and courteous basis PJ's at SentryWorld is seeking an energetic and enthusiastic Host to join our team. We work as a small team and have very high standards of service, meaning we work hard and with precision, while delivering on our hospitality standards of customer service. Apply today and come work at one of the most popular restaurants in central Wisconsin! What You’ll Do As a Host/Hostess, you will: Graciously greet guests, escort them to their table, and provide menus Assist management in maintaining details of the restaurant atmosphere Manage seating chart and monitor restaurant activity to determine seating and dining flow Manage restaurant waiting list during high volumes to accurately establish waiting times Assist fellow team members with side work including, but not limited to, cleaning and...
Sentry Stevens Point, WI Part Time
04/16/2026  
In this role, you will provide exceptional service to all guests by assisting them in a friendly, efficient, courteous and professional manner At The Inn at SentryWorld, our business is about people and the relationships we build. Our atmosphere is welcoming. And our team is genuine, dedicated, and insightful when it comes to delivering excellent service. If you enjoy forming long-lasting connections join our Front Desk team. What You’ll Do As a Front Desk Attendant, you will: Provide guests with a friendly and efficient check-in confirming guest information, verifying room rate, selecting room, coding electronic keys, providing welcome packet, and providing directions to room. Provide detailed and accurate information in person or over the phone regarding hotel policies, services, amenities, and special promotions. Assist guests with check-out ensuring room and services are correctly accounted and process payments and post charges to guest accounts. Balance all cash,...
Sentry Stevens Point, WI Full Time
04/14/2026  
In this role you would assist the banquet leadership team in the planning, organizing and execution of all banquet functions At SentryWorld, our business is built around people. We pride ourselves on the promise to deliver world-class services to our guests. The SentryWorld Events Team is seeking an energetic and enthusiastic Banquet Captain. This role is the perfect fit if you are looking to increase experience and responsibility in event planning, while ensuring our guests are receiving efficient and effective service throughout their event. What You'll Do As a Banquet Captain, you will partner with the Conference Services Managers & Banquet Manager to ensure the successful execution of events and will also act as a team leader in event set-up/take down, food and beverage service, and as a co-leader in the front-of-house event operations. In addition, you’ll: Oversee food and beverage service to ensure quality, consistency and that SentryWorld service standards...
Sentry Stevens Point, WI Full Time
04/14/2026  
Retirement Plan Consultants are dedicated to educating individual customers & participants on the advantages of participating in a retirement plan & operating an efficient plan. At Sentry, we focus on the future and want to help you do the same! Retirement Plan Consultants work with our sales team to provide the best service to both individual customer and participants. We provide everything you need to carve out a career filled with success and purpose including: Company car with gas card and permitted personal use Outstanding benefits and a 401(k)-program matching dollar for dollar up to the first 8% Work from home from your territory Opportunities for professional development and growth Outstanding training and support The territory for this position includes: Colorado, Kansas, Missouri, Nebraska, and Oklahoma Based on qualifications and experience of the selected candidate the base salary range is: $68,100-$102,100 for...
Sentry Denver, CO Full Time
04/14/2026  
In this role, you will play a crucial part in safeguarding Sentry’s claims integrity and regulatory compliance. As a Claims Audit & Compliance Specialist – Commercial Liability, you will develop and execute detailed audit plans to evaluate the accuracy of claims processing, compliance with regulations, and adherence to organizational policies. You will work with internal stakeholders at various levels of claims management to address audit findings and implement corrective measures. You will maintain documentation and stay informed about industry regulations, best practices, and emerging trends.    What You'll Do   Develop and implement comprehensive audit plans to assess claims processing accuracy, compliance with regulatory guidelines, and adherence to organizational policies. Analyze claims data and trends to identify potential areas for process improvement or risk mitigation. Complete daily/weekly control report reviews and investigate findings. Collaborate with...
Sentry Stevens Point, WI Full Time
04/14/2026  
Our highly trained Account Executives present specialized commercial insurance, 401K, and life insurance products that are perfectly designed for the industries we serve. You’re not just in it to win it. You want to crush it every time. Because that’s what our sales professionals do. Not just anyone has what it takes to build strong and profitable relationships. If you’re a unique performer, Sentry offers a career opportunity that soars beyond commercial insurance sales. We provide everything you need to carve out a sales career filled with success and purpose, including: High earning potential with base salary, commissions, monthly/annual incentives, plus recognition trips 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 Total currently estimated projected compensation range for...
Sentry Midland, TX Full Time
04/14/2026  
Agency Sales Managers are responsible for agency selection through identification of qualified agency partnerships for our non-standard auto and powersports Personal Lines Insurance. If you are in the greater Miami, FL area, are bilingual (English/Spanish), have the passion to unleash your talent, the drive to build new relationships, are a motivated self-starter and have strong organizational skills this is a great opportunity for you on our Agency Sales Team. Based on qualifications and experience, this position can be filled as an Agency Sales Manager I, Agency Sales Manager II, or Agency Sales Manager Senior. What You'll Do As the Agency Sales Manager you will be responsible for implementing plans to contribute to the achievement of agency produced sales, premium and loss ratio objectives.  In addition, you’ll: Oversee agency sales in South Florida Develop rapport to develop profitable business Provide comprehensive sales expertise to agents to...
Sentry Miami, FL Full Time
04/13/2026  
As an experienced litigator, you’ll apply your legal skills and experience to represent the interests of Sentry insureds by defending claims made under insurance policies. This position will require intermittent travel to Northern California to appear in court as necessary. Depending on qualifications and experience, this position can be filled at either a Trial Attorney or Senior Trial Attorney Level. What You’ll Do As a Trial Attorney, you'll apply your legal skills and experience to represent the interests of Sentry insureds. In additional, you will... Represent the interest of the insured and Sentry in defending claims, ensuring that there is no conflict of interest between the policyholder and Sentry. Handle a full caseload of minimally to moderately complex matters representing insureds up to, and including, through trial. Communicate and report to policyholders and claims associates on the progress of litigation, strategy, and evolution of matters....
Sentry CA Full Time
04/09/2026  
As an IT Product Analyst, you'll bridge the gap between business needs and IT solutions through analysis of IT product functionality to ensure alignment with strategic objectives. This position can be filled as an IT Product Analyst, Senior IT Product Analyst or IT Product Specialist based on qualifications and experience of the selected candidate. For candidates located in Illinois, based on experience and qualifications, the pay range for the IT Product Analyst is $74,900 - $112,300, and the Senior IT Product Analyst is $90,600 – $136,000. If hired as an IT Product Specialist, the pay range for the position is $109,700 – $164,500. 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....
Sentry Madison, WI Full Time
04/08/2026  
The State Product Manager-Nonstandard Auto is responsible for increasing profit, premium, & market share while meeting customers’ needs in an assigned region. Sentry Insurance is seeking a Product Manager to design and revise its Personal Lines Nonstandard Auto products. In this role, you will also bring to market product/distribution enhancements designed to attract and retain Non-Standard Auto customers in our Personal Lines portfolio. This will require the ability to communicate, and matrix manage throughout the organization. For this role we are open to considering applicants at our office locations in Stevens Point, WI, Madison, WI, Nashville, TN or current AWE associates. Based on qualifications and experience of the selected candidate, this role can be filled as an Associate Product Manager, Product Manager or Product Manager II. What You'll Do As a State Product Manager-Nonstandard Auto, you will develop and leverage expert knowledge of Sentry’s Personal...
Sentry Madison, WI Full Time
04/08/2026  
We are seeking a dynamic leader to oversee compliance programs, governance practices, and risk management processes for our Individual Life and Annuity business unit. This role ensures alignment with all state and federal regulatory requirements. In addition, you will lead and coordinate key business initiatives, collaborating across functional areas to ensure effective structuring and successful execution that meets business objectives and compliance expectations and organizational priorities. What You'll Do As a Compliance Manager Life & Annuity, you will: Monitor, interpret, and implement regulatory requirements related to individual life and annuity insurance products and services to ensure compliance with all relevant state and federal laws. Implement and maintain compliance programs, governance practices, and risk management processes aligned with state and federal regulatory requirements Serve as the primary compliance partner to Individual...
Sentry Stevens Point, WI Full Time
04/07/2026  
Agency Sales Managers are responsible for agency selection through identification of qualified agency partnerships for our non-standard auto and powersports Personal Lines Insurance. If you are in Kentucky and have the passion to unleash your talent, the drive to build new relationships, are a motivated self-starter and have strong organizational skills this is a great opportunity for you on our Agency Sales Team. Based on qualifications and experience, this position can be filled as an Agency Sales Manager I, Agency Sales Manager II, or Agency Sales Manager Senior. What You'll Do As the Agency Sales Manager you will be responsible for implementing plans to contribute to the achievement of agency produced sales, premium and loss ratio objectives.  In addition, you’ll: Oversee agency sales in the state of Kentucky and Indiana Develop rapport to develop profitable business Provide comprehensive sales expertise to agents to increase production Develop new and...
Sentry Louisville, KY Full Time
04/06/2026  
Our highly trained Account Executives present specialized commercial insurance, 401K, and life insurance products that are perfectly designed for the industries we serve. You’re not just in it to win it. You want to crush it every time. Because that’s what our sales professionals do. Not just anyone has what it takes to build strong and profitable relationships. If you’re a unique performer, Sentry offers a career opportunity that soars beyond commercial insurance sales. We provide everything you need to carve out a sales career filled with success and purpose, including: High earning potential with base salary, commissions, monthly/annual incentives, plus recognition trips 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 Total currently estimated projected compensation range for this...
Sentry Kansas City, MO Full Time