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Sentry Insurance jobs

Browse current Sentry Insurance openings that JobDrop found directly from the company's careers source.

Operations Technician Sr - Commercial Lines

Sentry Insurance · Multiple Locations, US · Posted 2026-09-01

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 su

OperationsTechnicianCommercialLines

Barista

Sentry Insurance · Stevens Point, WI, US · Posted 2026-09-01 · 1+ years

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 wonde

Barista

Director of Casualty Claims - Commercial Lines

Sentry Insurance · Stevens Point, WI, US · Posted 2026-08-31 · 8+ years

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

DirectorCasualtyClaimsCommercialLines

Cycle Dealership Sales Specialist

Sentry Insurance · Multiple Locations, US · Posted 2026-08-31 · 3+ years

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 dea

CycleDealershipSalesSpecialist

Scanning & Distribution Technician - Plover Archives (LT20)

Sentry Insurance · Stevens Point, WI, US · Posted 2026-08-31

As a Scanning & Distribution Technician, you will perform routine activities related to the scanning of records for multiple business unit. As a Scanning & Distribution Technician , you will prepare boxes and files for scanning, operate various data imaging equipment, perform quality reviews, and enter meta data and so

ScanningDistributionTechnicianPloverArchivesLT20

Customer Service Representative

Sentry Insurance · Multiple Locations, US · Posted 2026-08-27

Provide quality customer service via phone, email, and chat in a contact center. Resolve issues using standard procedures under close supervision. What You'll Do Take the customer service skills you have acquired over the years to the next level or make a change and start down your new career path today with our growin

ServiceRepresentative

Line/Grill Cook I at PJ's

Sentry Insurance · Stevens Point, WI, US · Posted 2026-08-26 · 0-2 years

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

LineGrillCook

Account Specialist

Sentry Insurance · Multiple Locations, US · Posted 2026-08-26 · 2+ years

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 c

AccountSpecialist

Documents Processing Technician Sr

Sentry Insurance · Stevens Point, WI, US · Posted 2026-08-25 · 2+ years

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 crea

DocumentsProcessingTechnician

Operations Technician Senior - Commercial Lines Transportation & Regional

Sentry Insurance · Stevens Point, WI, US · Posted 2026-08-25

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 beha

OperationsTechnicianCommercialLinesTransportationRegional

Senior Software Engineer (Hybrid Work Model)

Sentry Insurance · Stevens Point, WI, US · Posted 2026-08-25 · 2+ years

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 succ

SoftwareEngineerModel

Auto Claims Appraiser

Sentry Insurance · Multiple Locations, US · Posted 2026-08-21

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. Th

AutoClaimsAppraiser

Account Executive-Ohio and West Virginia Captive Territory

Sentry Insurance · Columbus, OH, US · Posted 2026-08-18

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 t

AccountExecutive-OhioWestVirginiaCaptiveTerritory

Retirement Plan Analyst

Sentry Insurance · Multiple Locations, US · Posted 2026-08-18 · 5+ years

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 s

Excel

Account Executive-Missouri Captive Territory

Sentry Insurance · Springfield, MO, US · Posted 2026-08-18

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 t

AccountExecutive-MissouriCaptiveTerritory

Business Product Analyst-Personal Lines

Sentry Insurance · Multiple Locations, US · Posted 2026-08-14 · 1+ years

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

ProductAnalyst-PersonalLines

Front Desk Attendant

Sentry Insurance · Stevens Point, WI, US · Posted 2026-08-10 · 1+ years

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 c

FrontDeskAttendant

Industrial Hygienist

Sentry Insurance · Multiple Locations, US · Posted 2026-08-06 · 2+ years

As an Industrial Hygienist you will complete Industrial Hygiene Services for our casualty line of business primarily for our National Account customers. Sentry’s dedication to customer service is embodied by our best employees. At Sentry, our associates take care of our customers with a passion for service and deliveri

IndustrialHygienist

Underwriting Manager - Middle Market

Sentry Insurance · Madison, WI, US · Posted 2026-08-04 · 2+ years

Manages a group of associates who have underwriting responsibility for all middle market lines, responsibly growing strategy, talent, and business. This position will be located in our Madison, WI Regional office under a hybrid work model. What You’ll Do: As an Underwriting Manager - Commercial Lines, you will oversee

UnderwritingMiddleMarket

Underwriting Leader

Sentry Insurance · Remote, Country not listed · Posted 2026-07-29 · 10+ years

At Sentry, our business is built around people. We are looking for a results-driven individual to lead and grow a book of businesses in the new market of Hawaii. We're passionate about offering the best services to our customers-and that spark begins with our team. This position will be responsible for revenue and prof

UnderwritingLeader

Human Resources Specialist

Sentry Insurance · Madison, WI, US · Posted 2026-07-29 · 3+ years

Sentry’s HR Specialists serve as the key HR representative in the field office in which they are located. This role will be located at our Middleton, WI office location in a hybrid work model. The HR Specialist provides support and guidance to Sentry managers and associates across a range of areas such as associate rel

Excel

Risk Control Consultant-Michigan

Sentry Insurance · Detroit, MI, US · Posted 2026-07-24 · 1-5 years

Plans and delivers safety/risk management services to insured customers and internal associates. We are currently seeking a risk control professional that is technically proficient, self-motivated and results driven to fill an open position within our East Shared Services division. You must be able to conduct comprehen

RiskControlConsultant-Michigan

HR Business Consultant

Sentry Insurance · Stevens Point, WI, US · Posted 2026-07-23 · 5+ years

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 mod

Consultant

Advanced Analytics Modeler (Hybrid Work Model)

Sentry Insurance · Stevens Point, WI, US · Posted 2026-07-11 · 2+ years

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 deci

AdvancedAnalyticsModelerModel

Account Executive-North Dakota and Minnesota Captive Territory

Sentry Insurance · Grand Forks, ND, US · Posted 2026-07-10

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 t

AccountExecutive-NorthDakotaMinnesotaCaptiveTerritory

Account Executive-Montana and Wyoming Captive Territory

Sentry Insurance · MT, US · Posted 2026-07-10

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 t

AccountExecutive-MontanaWyomingCaptiveTerritory

Retirement Plan Consultant

Sentry Insurance · Multiple Locations, US · Posted 2026-07-09 · 2-5 years

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 s

RetirementPlanConsultant

Account Executive- Alabama Captive Territory

Sentry Insurance · Montgomery, AL, US · Posted 2026-07-08

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 t

AccountExecutiveAlabamaCaptiveTerritory

Account Executive-Pennsylvania Captive Territory

Sentry Insurance · Scranton, PA, US · Posted 2026-07-08

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 t

AccountExecutive-PennsylvaniaCaptiveTerritory

Account Executive-Indiana Captive Territory

Sentry Insurance · Evansville, IN, US · Posted 2026-07-08

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 t

AccountExecutive-IndianaCaptiveTerritory