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.

07/22/2026  
As an Operations Technician – Commercial Lines (CL), you will support operational and underwriting processes and handle a variety of policy transactions. What You'll Do •Document and maintain customer information and forms necessary for policies and/or policy changes in various systems  •Respond to email inquiries from both internal and external customers •Prepare and assemble policies and/or policy changes for mailing or electronic distribution •Enter, delete, or update driver information per guidelines within the policy administration system •Perform filing, retrieval, and distribution of various materials and documents in accordance with prescribed departments’ systems and practices •Ensures all data and materials meet company standards for compliance, completeness and quality  •Upload files to content retention systems   What it Takes •High School degree or equivalent •Experience in a customer service or office environment preferred •Ability to work with detail and...
Sentry Stevens Point, WI Full Time
07/21/2026  
As a Security Officer, you'll monitor numerous properties to provide safety and security to Sentry associates, visitors, and assets. At Sentry, security is one of our top priorities. To ensure our associates are safe and that our properties are secured, we are seeking a security-focused individual to join our Security team. In this key full-time opportunity, you’ll grow your physical security experience in a dedicated and rewarding environment while knowing you’ve made an impact to keep our teams are safe. We are currently looking for a Security Officer to assist our 3rd shift team from 10:30pm-6:30am Monday through Friday. There is a rotating 3rd shift weekend from 6:30pm-6:30am. This role will require flexibility with the availability to work nights, weekends, holidays, and special events as required. What You'll Do As a Security Officer, you will: Patrol and monitor interior and exterior of numerous premises to prevent and detect any risks to Sentry associates...
Sentry Stevens Point, WI Full Time
07/21/2026  
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. This role is required to work standard hours of Monday - Friday from 8 AM - 4:30 PM. This role will follow Sentry's hybrid work model and can work out of Davenport, Iowa or the Strongs Stevens Point, WI Sentry office. 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...
Sentry Davenport, IA Full Time
07/21/2026  
You’ll work closely with a team of engineers to develop, test, and maintain software applications, systems, or platforms. 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. For this position, Sentry does not offer employment to holders of F-1, J-1, and H-1 Visas. Our team is seeking a talented Software Developer looking to make an impact. You’ll play a crucial role in developing and enhancing custom solutions that support our operations, collaborating with skilled developers, engineers, quality analysts, and product analysts. You’ll be involved in the full software development lifecycle using technologies such as Artificial Intelligence, C#, Angular, SQL, and more in a hybrid cloud infrastructure. If you are passionate about technology, enjoy solving complex problems,...
Sentry Stevens Point, WI Full Time
07/21/2026  
This position will be located in our Sentry Strongs office in Stevens Point, WI. 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, 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 business submissions and policy updates •Perform moderately complex operations support duties and handle production problem listings •Utilize various systems and sites to manage and process requests related to the Regional businesses •Use problem-solving skills and best judgment to work...
Sentry Stevens Point, WI Full Time
07/20/2026  
This role works with security domains and maintains and improves the associated systems to reduce security risks to the organization. Sentry is looking for an experienced information security professional to join the Information Security Operations team. This role works with security domains and maintains and improves the associated systems to reduce security risks to the organization. What You'll Do As an Information Security Platform Engineer, you will: Be responsible for end-to-end management of at least one core security platform. Provide technical maintenance services and help with implementation of patches to integrated security systems and solutions ensuring continuous availability and operations. Conduct monitoring through automated functional and performance testing, investigate potential problems and determine solutions to avoid service interruptions. Research, propose and implement new features and functions for assigned security domain to...
Sentry Stevens Point, WI Full Time
07/17/2026  
Processes soiled and clean linen using a variety of equipment including commercial-sized washing machines, dryers, flatwork ironers, folding machines and heat transfer machines. At The Inn at SentryWorld, we focus on all aspects of guest experience. We are looking for   a   full - time   Laundry   Attendant to help in creating that exceptional experience. You’ll work closely with our housekeeping team to ensure inventory levels are supplied to the floors in a timely and efficient manner. You’ll be self-motivated, organized and have a positive attitude.    Apply today to join our detail-oriented team as we create a memorable experience for our guests!    What You’ll Do   As our Laundry Attendant, you’ll sort, wash, press and fold bedding and towels using our equipment. In addition, you’ll:    Sort soiled linen by type and clean according to directions and standards.    Ensure linens are available for guest...
Sentry Stevens Point, WI Full Time
07/16/2026  
Investigate and resolve insurance claims in an efficient and accurate manner. You’ll independently manage a caseload, negotiate settlements, and communicate with all parties. This position will be located in our Stevens Point, WI; Nashville, TN; Davenport, IA; Goldsboro, NC; Madison, WI; El Paso, TX; or Edwardsville, Il office locations under a hybrid work model. What You’ll Do: As a Senior Claims Representative on our Commercial Lines - Liability teams, you'll provide superior service by conducting prompt claim investigations, which includes evaluating coverage, determining liability, and settlement of damages. In addition, you will: Verify coverages by thoroughly reviewing the policy and interpreting policy terms, conditions, and language, which may require working with coverage counsel. Evaluate complex liability by taking recorded statements from involved parties and witnesses, reviewing police reports, and compiling other pertinent evidence. Analyze all...
Sentry Stevens Point, WI Full Time
07/16/2026  
Sentry’s Project Managers manage department specific projects and portfolio initiatives. Join the Project Management Office where we lead a variety of strategic priorities from cloud, platform, and infrastructure projects to marketing or business initiatives. What You'll Do As a Project Manager, you will: Deliver department level projects or assists with cross-department projects or portions of portfolio level initiatives, typically involving multiple teams across IT functions or business areas. Facilitate communication, problem-solving and negotiation across teams, while collaborating at the manager to director level to ensure stakeholder and general project alignment. Lead core project delivery activities such as planning, schedule management and project risk management including contributing ideas and content such as solutions, risks, issues, and other project related artifacts. Provide financial tracking and cost management support for department level...
Sentry Stevens Point, WI Full Time
07/16/2026  
Provide operational support to attorneys & paralegals, using your skills for research, drafting documents, developing forms, and handling court filings. This position will report to our Scottsdale, AZ office under our hybrid work model. What You'll Do: Assists attorneys and paralegals in gathering standard information. This may include but is not limited to medical records, photos, police reports, statements, bills, guardianship materials, etc Provides support on various ad hoc projects to address specific legal related needs. Prepares standard respondence regarding demands for bills of particulars, jury demands, discovery pleadings, and other legal matters as directed by attorneys Establishes and maintains department files, records management, case management system, and attorneys time/billing for cases. Protects and maintains confidentiality and privilege of all legal matters Performs other job-related duties as assigned from time to time...
Sentry Scottsdale, AZ Full Time
07/16/2026  
As a groundskeeper you would perform a variety of duties to support the ongoing care and maintenance of the grounds and related areas at SentryWorld Golf Digest lists SentryWorld as one of America’s 100 Greatest Public Golf Courses. Join the team that’s responsible for making sure we continue to earn that honor! We are seeking full time, seasonal Golf Course Groundskeepers to join us at SentryWorld as we look ahead to the 2026 season! Apply today and spend your days on one of the finest courses in the country! We are looking for someone that is focused, driven, and has a passion for the golf course maintenance field! If you think you are a good fit, we would love to hear from you.   What You'll Do As a Groundskeeper, you’ll: Perform maintenance of grounds around SentryWorld Properties. Some tasks include mowing, string trimming, edging, mulching, etc. to enhance the appearance of SentryWorld Prepare playing surfaces on the golf course such as greens, tees, fairways,...
Sentry Stevens Point, WI Full Time
07/15/2026  
Unlock your potential by joining an integrated team of Accounting professionals in Treasury Services and learn the dynamic world of investments and separate accounts. This position can be filled as an Associate Financial Analyst or Financial Analyst based on the selected candidate’s qualifications and experience. This position offers career growth opportunities for the right candidate. This position will be located at our Office in Stevens Point, WI in a hybrid work model and is not a fully remote opportunity. 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 member of our Treasury Services team, you will play an integral role to the continued success of our team by: Completing the accounting, processing, and reconciliations for various integrated systems for investments and separate accounts Applying appropriate accounting principles and assuring proper recording, assembling, and...
Sentry Stevens Point, WI Full Time
07/14/2026  
Workplace Technology Engineers are responsible for leading the design, implementation, and maintenance of innovative technology solutions. 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 use of emerging technologies, tools, and vendors you’ll have the ability to identify opportunities for innovation and improvement within the workplace technology environment. 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...
Sentry Stevens Point, WI Full Time
07/14/2026  
Provides support to Underwriters by handling a variety of tasks needed for their evaluation of new and renewal business. As an Assistant Underwriter- Transportation, you’ll work closely with other Business Products functions and interacts daily with the product and premium services, premium audit, safety sciences, accounting, and operations support units to ensure service and quality objectives are met. What You’ll Do: Receive and respond to phone calls and emails from agents, brokers, and sales personnel regarding all coverage and transaction types to obtain information needed to properly underwrite, price, and program policies/accounts. Work on underwriting assignments such as loss and risk exposure evaluation through the use of manuals, established procedures, and collected information. Refer business outside of authority limit. Apply underwriting policies, philosophies, and procedures to evaluate the overall acceptability of risk to determine if it fits...
Sentry Stevens Point, WI Full Time
07/14/2026  
As a Cycle Dealership Sales Specialist, you will contribute to profitable premium growth by increasing motorcycle dealer engagement with our motorcycle insurance product. Sentry’s motorcycle team is seeking a motivated, self-starter who has a passion for building and maintaining strong relationships with motorcycle dealers within a defined territory.  This position will manage a large geographic territory and will be staffed within the Central US territory.  What You'll Do As a Cycle Dealership Sales Specialist, you will coordinate and lead motorcycle dealership training, relationship management, complaint handling, prospecting and communication within your territory.  Additionally, you will: Promote product and brand at assigned, motorcycle events to identify and foster production sources and relationships. Provide insurance product expertise and leads product and related process training efforts for dealerships and related affinity associations. Provide...
Sentry Madison, WI Full Time
07/13/2026  
Oversees the operational and strategic management of the claims supplier portfolio to optimize the value, cost, and risk. This role will report to our Stevens Point, WI office. What You’ll Do: Our Claims Supplier Management Analyst will oversee the operational and strategic management of the claims supplier portfolio to optimize the value, cost, and risk. You will collaborate with claims management (supplier relationship and application owners), IT management, and corporate procurement in supplier acquisition, compliance, maintenance renewals, service level agreement adherence, and more. In addition, you will… Maintain a comprehensive listing and overview of claims suppliers and services. Compile and monitor supplier contract dates and provide timely awareness of renewal dates to enable visibility of key contract items such as contract terms, pricing, current costs, and SLA Adherence. Coordinate quarterly business reviews/annual reviews/partnership reviews...
Sentry Stevens Point, WI Full Time
07/10/2026  
The Advanced Analytics Modeler translates raw data into actionable business information. This role, in the Advanced Analytics Department, applies economic, quantitative, and statistical skills in the development of pricing, underwriting, sales, and claims models to achieve profitable growth and make sound business decisions across all areas of Sentry Insurance. This position can be filled as an Advanced Analytics Modeler I or Advanced Analytics Modeler II based on the qualifications and experience of the selected candidate. This position will be located at our Office in Stevens Point, WI in a hybrid work model and is not a fully remote opportunity. For this position, Sentry does not offer employment to holders of F-1, J-1, and H-1 Visas. What You’ll Do Build comprehensive analytics solutions to improve business outcomes such as pricing accuracy, resource efficiencies, business workflows, and identification of trends and opportunities. Identify data...
Sentry Stevens Point, WI Full Time
07/09/2026  
As an HR Business Consultant, you will provide a broad range of strategic human resources consulting services to leaders. Our HR Business Consultants are thought leaders who balance business and associate needs when problem-solving and creating integrated solutions. They utilize a deep understanding of our business model to proactively translate the area’s strategies into HR solutions that best enable the business teams to meet its strategic objectives. What You'll Do As an HR Business Consultant, you will: Build strategic relationships with business leaders and develop trust and business acumen to deliver on business needs. Partner with HR centers of excellence to execute on key processes related to employee relations, staffing, training, performance management, succession planning, compensation and benefits for business partners. Identify, define and recommend solutions to address the needs of the business while taking account of the broad impact on the...
Sentry Stevens Point, WI Full Time
07/09/2026  
We’re seeking a self-motivated professional with technical and analytical skills to join the Internal Audit team as an Internal Auditor. You’ve got a passion for helping others and our goal is to turn that passion into action.  At Sentry, we care about delivering long-term results. Our associates embody this same future-focused approach – meeting challenges head-on and offering solutions and pricing that keeps customers coming back down the line. This position will be located at our Office in Stevens Point, WI in a hybrid work model and is not a fully remote opportunity. For this position, Sentry does not offer employment to holders of F-1, J-1, and H-1 Visas. Based on the qualifications and experience of the selected candidate, this position can be filled as an Associate Financial Analyst or an Internal Auditor. What You’ll Do As an Internal Auditor, you will Conduct testing for risk-based audits by analyzing and evaluating the adequacy and...
Sentry Stevens Point, WI Full Time
07/09/2026  
This role markets Commercial Lines products, builds agency partnerships, leads underwriting for new/complex business, manages growth and profitability, and maintains market visibility. The preferred candidate for this position will reside in the Jackson, MS - Mobile, AL - Birmingham, AL triangle with travel required in and around that territory. What You'll Do The Territory Underwriter Specialist will be responsible for agent and broker relationships. In addition, you’ll: Solicit accounts through select agents and brokers Evaluate, underwrite, and price prospective accounts to select independent agents Serve as the primary contact with assigned agents and brokers Provide comprehensive sales expertise to increase production through agency channels Work with assigned agents and brokers on the coordinating of resolutions What it Takes Bachelor’s degree or equivalent work experience Minimum of 5 years related work experience, with multi-line middle...
Sentry AL Full Time