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.

07/20/2026  
Supports the client services management team and designated clients through a variety of tasks including gathering information and facilitating general client interactions. This associate will utilize multiple systems to monitor and resolve service-related items that arise to assist with timely completion of service items, annual non-discrimination testing, and other compliance related items. Works closely with 401(k) colleagues for continued education and development of 401(k) technical knowledge. What You'll Do   As an Associate Client Services Specialist,   you will:  Monitor and maintain workflow tasks for assigned clients to ensure requests and services are completed within the required deadlines  Monitor incoming email and voice messages while corresponding with clients to provide accurate information regarding employer contributions, payroll, and plan information  Collect, verify, and update required customer information accurately within Sentry systems...
Sentry Stevens Point, WI Full Time
07/20/2026  
Performs routine activities related to the scanning of records for multiple business units  As a Scanning  & Distribution Technician, you will perform routine activities related to the scanning of records for multiple business units; prepare boxes and files for scanning, operate various data imaging equipment, perform quality reviews, and enter meta data and source information according to business area guidelines.  We are currently seeking candidates to fill our Document Scanning Technician role for a 3-5 year assignment. This position will be located on-site at the Dixon-Stevens Point Office and will be regularly scheduled to work Full-time 40- Hours a week. The hours for this position are between 7 a.m.- 5 p.m., Monday-Friday. What You’ll Do Performs various activities as they relate to scanning of physical files and records. Prepares documents for scanning, which may include document sorting, page separation, photocopying, unbinding, and repositioning files...
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
07/20/2026  
Ensures quality customer service by interpreting phone calls for personal and commercial lines insureds and claimants. Translates and transcribes documents and recordings accurately. What You'll Do As the translator for Sentry Insurance, you will translate verbally phone conversations and rewrite documents in both English and Spanish. This individual would also follow a hybrid work model and is eligible to work out of our Stevens Point, WI, El Paso, TX, Freeport, IL or Goldsboro, NC office locations. For Sentry, our flexible schedule would be Mondays and Fridays are optional work from home days and Tuesday, Wednesday and Thursday are in office days. Additionally, you’ll: Participate on phone calls between Sentry and Claimants Interpret various dialect meanings while translating verbally or in written form Provide translation services to all Sentry offices Translate a high volume of calls daily Provide a high quality of customer service for internal and...
Sentry Goldsboro, NC Full Time
07/17/2026  
Are you organized, detail-oriented, and enjoy keeping things running smoothly behind the scenes? We’re looking for a Records & Materials Handler to join our team! In this role, you’ll be responsible for sorting, filing, and maintaining our stored records, ensuring easy access and timely purging according to established policies. You’ll also play a key part in fulfilling supply requisitions, pulling and packing orders for Sentry personnel nationwide, and managing inventory documentation.  If you thrive in a structured environment and have a knack for precision, we encourage you to apply!    What You'll Do   As a Records & Materials Handler, you will: Logs and processes incoming records and closed files i.e., sorts incoming boxes, assures bar code label is affixed, stages files in groups according to retention date, determines appropriate storage location according to established procedures, records files in scanner and transfers file information to database, places...
Sentry Stevens Point, WI Part 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
07/15/2026  
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 and renewal transactions 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 Transportation and Regional businesses •Use problem-solving skills...
Sentry Stevens Point, WI Full Time
07/15/2026  
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 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 is not a...
Sentry Madison, 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