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...

Kick off your career at Sentry! Dive into real auto claims from day one, gain hands-on training, assess liability, and grow into a confident, knowledgeable claims expert Associates will be based out of our Nashville, TN or Davenport, IA office following the hybrid work model. 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...

Kick off your insurance career! Dive into real auto claims from day one, gain hands-on training, assess liability, and grow into a confident, knowledgeable claims expert. An entry-level Claims Representative position requi res a learning nature, empathy and interpersonal skills along with a strong desire to assist customers.     We're currently recruiting for a Claims Representative to work within our Motorcycle Unit   This position will be located at our Davenport, IA office following the hybrid work model —this role is NOT available for remote work.     What You'll Do   As an entry-level Claims Rep, 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...

Working as a Claims Technician, you’ll provide critical support to the claims team, assisting with tasks that range from moderate to advance in complexity. Your responsibilities will include maintaining accurate records, processing claim payments, scheduling medical appointments, and preparing various forms and documents for mailing or electronic submission. You will also manage incoming and outgoing mail, assist with tasks within the claims system, and monitor shared mailboxes to ensure timely follow-up. In this role, you’ll collaborate with customers, vendors, attorneys, and internal claims associates to help resolve issues and support the efficient progression of claims toward resolution. This position will be located at our Nashville, TN office following the hybrid work model and is NOT available for remote work. What You'll Do As a Claims Technician, you will: Analyze and process complex bills, checks, and invoices for proper coding and payment, including...

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...

As a PJ restaurant server, you’ll provide friendly, efficient service. Ensure every guest feels welcome, comfortable, important, and relaxed during their visit At Sentry, the best parts of our business come from our very own backyard. All across our organization, we work to cultivate homegrown talent; people like you are curious, hardworking, and always looking to improve. At PJ’s Restaurant, located within SentryWorld, we specialize in homemade recipes that are the Wisconsin focus including, cheese curds, fish fry, and cocktails. We work as a small team and have very high standards of service, meaning we work hard and with precision. We are looking for someone that is focused, passionate, empathetic, and takes hospitality seriously. If you think you are a good fit, we would love to hear from you! What You’ll Do As Server, you will be responsible for providing guests with friendly and efficient food and beverage service. In addition, you’ll: Provide positive...

This position can be filled working out of Sentry's Stevens Point, WI; Davenport, IA; or Edwardsville, IL offices. 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, sales producers, 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  •Respond to internal and external information requests, including email and phone inquiries. Effectively explain plan details and/or processing requirements  •Document and maintain customer policy information. Gathers necessary data from various sources, reviews data for accuracy and ensures...

Greets customers and answers questions to help with food and beverage selections. 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 guests , but they also create an experience.   What You’ll Do   As a barista at T he 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 equipment, cases, dishes, counters, refrigerators,...

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...

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...

Our PJ's team is looking to add a Line/Grill Cook to our culinary department. We are looking for people like you who are curious, hardworking, and always looking to improve. At SentryWorld, the best parts of our business come from our very own backyard. All across our organization, we work to cultivate homegrown talent; people like you are curious, hardworking, and always looking to improve. Our friendly team at SentryWorld is looking for a Line/Grill Cook for our culinary team and we want you to join us.   Current Line/Grill Cook opportunities at SentryWorld include:  PJ's Restaurant seeking Full-time (30-40 hours)  If you think you’d be a good fit, we’d love to hear from you.    What You’ll Do   As a Line/Grill Cook, you’ll:  Prepare a variety of dishes made from our very own recipes  Responsible for setting up food preparation lines including grill, sauté, Fry cook, desert, pastry and salad lines.  Set up stations and collect all necessary supplies...

We are seeking a Software Engineer or Senior Software Engineer to join our Commercial Lines IT team. 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. This position can be filled as a Software Engineer or Senior Software Engineer based on the qualifications and experience of the selected candidate. Our ideal candidate will have experience with modern web and enterprise technologies, cloud services, & microservices architectures. This role offers opportunities to work with cutting-edge digital transformation initiatives across our insurance business lines.  For this position, Sentry does not offer employment to holders of F-1, J-1, and H-1 Visas. What You’ll Do You’ll be a valuable contributor to our team. As a Sentry associate, we believe in your skills and...

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 by handling 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 and best judgment to work with internal business units to resolve problems...

Are you an expert in word processing & document development systems? We’re looking for a Document Processing Tech Sr to help our team create, shape complex documents, forms & templates We’re looking for a Documents Processing Tech Sr to utilize their expertise in word processing and document development systems to create and modify complex documents and forms for our customers. In this role, you’ll also assist in developing department standard, procedures and provide valuable technical expertise and training to both our document technicians and customers. If you’re ready to make an impact with your technical skills and collaborative spirit, apply today!   What You'll Do   Utilize technical expertise of word processing/document development hardware/software to create and modify programs to produce complex documents, templates and forms. Communicate with customers to determine and/or clarify project needs and may discuss other available options that would meet...

Lead efficient claim decisions by assessing losses, building estimates, and securing fair settlements while collaborating with repair teams and tracking the latest repair technology. This position will be staffed out of our Nashville, TN or Davenport, IA, or Stevens Point, WI offices following the hybrid work model. This position is NOT available for remote work. What You'll Do   The focus of this role is conducting inspections on auto damage to prepare and review repair estimates. Additionally, you’ll:  Virtually inspect damaged vehicles to assess the extent of structural, body, mechanical, and interior damage. Prepare detailed, accurate, and comprehensive damage reports and repair estimates using specialized software. Maintain detailed records of appraisals, photographs, and communications related to each claim.  Review and interpret insurance policies to determine coverage and liability. Negotiate settlements with repair facilities and clients, ensuring...

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...

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...

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...

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...

In this role, you will provide technical knowledge & support during the sales of 401(k) products to achieve growth, retention & profitability among Sentry Direct Writer sales producers. This position can be filled as a Retirement Plan Analyst or Senior Retirement Plan Analyst based on the selected candidate’s related skills and experience. This position will be located at our office in Stevens Point, WI or Madison, 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 Senior Retirement Plan Analyst , you’ll leverage your technical retirement plan knowledge and experience in the development and marketing of 401(k) products. Along with this responsibility you will: Provide project coordination and support including, but not limited to tracking and coordination of various projects and initiatives ensuring the on-time and in-scope...