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.

06/04/2026  
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
06/04/2026  
Join Sentry's team as a Corporate and Transactional Paralegal! Sentry’s Corporate and Transactional Paralegals perform a variety of complex legal activities, including reviewing and helping negotiate a variety of commercial agreements, assisting with maintenance of Sentry’s trademark portfolio, and mergers and acquisitions activities.   What You'll Do As a Corporate and Transactional Paralegal, you will: Review and negotiate legal agreements, providing guidance and recommendations to business stakeholders on agreement terms and alternative provisions to resolve differences between the organization and external parties. Champion the adoption of new legal technologies, including AI, into Sentry’s corporate and transactional practice area by actively reviewing, evaluating, and implementing them into legal workflows. This involves providing thoughtful guidance on responsible technology use while fostering continuous innovation and evolution of processes and tools....
Sentry Stevens Point, WI Full Time
06/04/2026  
Supports Enterprise Scanning and Mail Services by sorting and preparing incoming/outgoing mail and packages, operating imaging/mailroom equipment, and handling admin tasks. We are looking to add a Scanning and Distribution Tech to our Stevens Point, WI office team! Our Scanning and Distribution Tech provides support to the Enterprise Scanning and Mail Services organization by performing routine activities related to the distribution of incoming and outgoing mail for various business units; sorts and preps incoming mail, preps outgoing mail/packages, operates various data imaging and mailroom equipment and performs miscellaneous administrative duties.       This role will report to our Stevens Point, WI office and will   be   regularly   scheduled to work   less than 20 hours a week .   Current hours for the role would be Mondays 6:15-2:45pm and Fridays 6:15am to 10:15am CST.   What You’ll Do The Scanning & Distribution Technician...
Sentry Stevens Point, WI Part Time
06/03/2026  
Responsible for operating and maintaining corporate high speed printers, mail inserters and peripheral equipment Our Print to Mail area is responsible for overseeing the running of print jobs from batch computer systems. Print output includes billing statements, policy documents and other important materials. Our team is responsible for ensuring that the machines are operating correctly, and that the output meets quality expectations. This position will be located on-site at the Sentry Home Office in Stevens Point, WI and will be regularly scheduled to work Part-Time Less Than 20 Hours a week. What You'll Do As a Print to Mail Operator I, you will: Assist in operating the control console of high speed printers in accordance with operating instructions, to process data. Assist in responding to operating and computer output instructions. May assist in using, monitoring and modifying the inserter setups to process the daily work on the inserting machines. May access the...
Sentry Stevens Point, WI Part Time
06/03/2026  
Oversees outfitter desk providing guests with rentals and recommendations on recreational activities, services, dining, and other local amenities. At the Inn at SentryWorld, we focus on the guest experience. We’re looking for a Seasonal Full-time Outfitter Attendant, who’ll assist guests with rentals and suggestions on recreational activities, dining, and local events. You’ll be the premier person to connect our guests with a great local experience. What You’ll Do As an Outfitter Attendant, you will: Work in coordination with the other Front Office Team Members to create a warm, welcoming environment for each and every guest. You will serve as the primary contact for guests interested in learning more about our SentryWorld facilities while exhibiting courteous manners in accordance with Sentry Services Standards Increase guest utilization of SentryWorld facilities by promoting our services, activities, and amenities. Assist guests in the Outfitter and answer...
Sentry Stevens Point, WI Full Time
06/02/2026  
Our onsite Baristas not only craft wonderful beverages for our guests, but they also create an experience. The Inn at SentryWorld 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. Our onsite Baristas   not only craft wonderful beverages for our   guest , but they also create an experience.   What   You’ll   Do   As a barista at the   Library , 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...
Sentry Stevens Point, WI Part Time
06/02/2026  
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. 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...
Sentry El Paso, TX Full Time
06/01/2026  
In this role, you will work hand in hand with Business partners to document and file our products with state DOIs, as well as to help build systematic underwriting rules. As one of the largest mutual insurance companies in the US, Sentry is committed to offering coverage at a competitive price and providing outstanding service and support. To offer our customers competitive products and outstanding service it takes an effective team. A Personal Lines Product Analyst is a key part of the team in our Madison, WI or Stevens Point, WI office. This is a great opportunity to start or grow your career, while taking on new challenges to develop professionally. Bring your strong curiosity, multi-tasking skills and a “can do” attitude to this opportunity. This position can be filled as a Product Analyst or Associate Product Analyst based on the selected candidate’s related skills and experience. This position will be located at our office in Madison, WI in a hybrid work model and...
Sentry Madison, WI Full Time
06/01/2026  
Sentry is seeking a top talent to join our part 91 Corporate Aviation team flying 2000LXS and G600 aircraft! A warm welcome, gracious service and a safe and comfortable feeling, makes our customers’ journey something they will always remember.  If you are a highly customer-focused individual who strives for the best and takes pride in getting the job done, we would like to hear from you.  This position is not commutable. Applicant will reside within 1 hour of the Mosinee KCWA airport. What You’ll Do Our First Officer – Corporate Aviation is responsible for assisting the captain to safely transporting passengers to the appropriate destination.  Sentry entrusts in you to provide “First Class” customer service to our corporate travelers.  To ensure this, you will: Assist the Captain in the safe transportation of passengers and the maintenance of high safety standards for the best possible aircraft performance.  Assist the Captain in taking corrective action in dealing...
Sentry Stevens Point, WI Full Time
05/29/2026  
This role will be based out of our Cincinnati, OH regional offices and will follow the Sentry Hybrid work model schedule. In this position, you will support the commercial lines (CL) underwriting processes by handling a variety of transactions and policy changes. This will support the review and acceptance/decline of new or renewal CL business with a degree of specialization and/or across multiple lines of business. Partnering with underwriters and sales producers, you will compile and/or shares policy and coverage information for assigned business and customers. They will also ensure proper documentation and record management according to regulatory and Sentry standards.  What You'll Do •Ensure sufficient information is obtained and forwarded to the underwriter for proper risk evaluation •Using manuals, established procedures, and collected information, prepare the underwriting file for the underwriter by completing loss summaries, reviewing driver acceptability,...
Sentry Cincinnati, OH Full Time
05/27/2026  
This role is required to work in Sentry's hybrid model out of the Cincinnatti, OH regional office. What You’ll Do: As an Underwriting Support Specialist, you will be responsible for specific territories utilizing your talents to: •Documents and maintains customer information and forms necessary for policies and/or policy changes in various systems. Handles the most complex transactions by gathering all necessary data from various sources, updating applicable systems, reviewing output for accuracy and completeness, and ensuring appropriate resolution. Ensures that data and materials meet company standards for compliance, completeness, and quality. •Collaborates with underwriters and agents to prepare new or renewal files for underwriters within an assigned territory, producing risk/exposure reports and compiling information. Compiles underwriting electronic records and forms, sales quotes, and/or business contracts. May correspond with customers, sales producers, and/or...
Sentry Cincinnati, OH Full Time
05/26/2026  
Design protective solutions leveraging security expertise, balancing security & innovation. Guide teams, anticipate trends, and secure business initiatives. As an Information Security Architect, you will leverage expertise in one or more security domains such as network security, security engineering, identity and access management, security operations, and others, as well as having a broad understanding of Information Security to design protective solutions for the business, balancing security with innovation.  You will consider the impact on business and IT processes, meet regulatory requirements, and collaborate with diverse teams to deliver optimal security solutions.  You will work to secure business to business initiatives, third-party relationships, and outsourced solutions by providing effective security requirements. You will provide guidance on current security issues to technical teams and leaders throughout the organization, anticipate industry trends, and...
Sentry Stevens Point, WI Full Time
05/22/2026  
As a Claims Technical Specialist, you will play an integral role in ensuring the effective management of complex and high-exposure claims with a focus on commercial property losses. You will apply your technical expertise, regulatory knowledge, leadership skills, and a strong commitment to ensuring delivery of high-quality outcomes for both the organization and its customers. What You'll Do   Effectively assess and address complex claim issues by applying comprehensive understanding of the organization's standards, procedures, and philosophies related to claims handling. Stay abreast of legislative changes, court decisions, and industry trends that may impact claims practices. Recommend and implement changes to claims processes and practices as necessary. Provide guidance and oversight to claims staff, ensuring that claims are handled efficiently and effectively. Offer expertise on technical aspects of claims handling and resolve any challenges that may arise....
Sentry Stevens Point, WI Full Time
05/22/2026  
We are seeking a Workplace Technology Engineer to join our team and play a key role in supporting and evolving our workplace technology ecosystem. This position will focus primarily on the Microsoft 365 platform, including Exchange, SharePoint, and Teams, which are foundational to our communication, collaboration, and productivity environment. This position is eligible to work on a hybrid basis out of Sentry's Stevens Point, WI or Madison, WI office locations. 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. 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...
Sentry Stevens Point, WI Full Time
05/21/2026  
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 position...
Sentry Marietta, GA Full Time
05/21/2026  
The Library 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 The Library, nestled within The Inn at SentryWorld, offers a warm and inviting atmosphere, serving a new concept in farm to table dining. Known for its commitment to quality and locally sourced ingredients, this venture brings the dining experience to a new level. What You’ll Do As a 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 Share knowledge of SentryWorld facilities by promoting our services, activities, and amenities. Assist fellow team members with side work including, but not limited to turning...
Sentry Stevens Point, WI Part Time
05/15/2026  
Responsible for providing a positive, energetic and friendly bar experience to all guests at PJ's Restaurant Our friendly team at PJ’s is looking to add energetic and experienced Bartenders with knowledge of contemporary cocktails, beer, and wine and we want you to join us. We’ll provide the training you need and the positive environment you deserve. Apply today to come work at one of the most popular restaurants in central Wisconsin! What You’ll Do To create a positive experience for our guests, you’ll: Provide outstanding customer service to all customers and promote a positive image of Sentry facilities. Prepare and serve beverages in a high-volume atmosphere. Receive and serve food orders taken at the bar. Record all sales and collect money for payment and is responsible for guest checks. Maintain the cleanliness of the bar area. What it Takes   Age requirement of 21+ required High School Diploma or equivalent work experience....
Sentry Stevens Point, WI Part Time
05/14/2026  
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 this position is...
Sentry Birmingham, AL Full Time
05/14/2026  
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 this position is...
Sentry Danbury, CT Full Time
05/13/2026  
Sentry is seeking a motivated Senior Actuarial Analyst to support pricing and actuarial analysis across our Small Commercial insurance portfolio. Working under the guidance of actuarial leadership, this role will help develop the analytical foundation that supports our small commercial products. You will contribute directly to pricing and product decisions that impact the future of Small Commercial at Sentry. This position can be filled as an Actuarial Analyst, Actuarial Analyst II, or a Senior Actuarial Analyst based on the qualifications and experience of the selected candidate. This position works within Sentry's hybrid work model and is eligible to work on a hybrid-basis out of our Stevens Point, WI or Madison, WI office locations. What You'll Do As an Actuarial Analyst, you will: Compile, validate, and analyze data used in actuarial studies supporting pricing, reserving, and rate adequacy for Small Commercial products. Assist in the preparation of state rate...
Sentry Madison, WI Full Time