JobDrop

Sentry Insurance jobs

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

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 · 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

Project Manager (Hybrid Work Model)

Sentry Insurance · Madison, WI, US · Posted 2026-08-13 · 5+ years

Sentry’s Project Managers manage department specific projects and portfolio 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 busi

ProjectModel

Infrastructure and Platform Engineering Manager (Hybrid Work Model)

Sentry Insurance · Multiple Locations, US · Posted 2026-08-12 · 5+ years

Lead a team of Platform Engineers responsible for the reliability, performance, and evolution of the critical platforms and infrastructure that power Sentry’s enterprise IT operations. 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’r

InfrastructurePlatformEngineeringModel

Premium Audit Technician

Sentry Insurance · Multiple Locations, US · Posted 2026-08-11

This position can be located in our Stevens Point, or Madison, WI office(s) and will follow Sentry’s current hybrid model of 3 days in-office. Entry level role focused on supporting the premium audit function. Communicates with internal and external customers and supports a growing book of middle and large businesses a

PremiumAuditTechnician

Product Specialist - Small Commercial

Sentry Insurance · Madison, WI, US · Posted 2026-08-10 · 0-3 years

Sentry is seeking a motivated Product Specialist to help power data driven decision making across the Small Commercial business unit. The focus is on Direct Sales Channel and Customer Acquisition support. This includes evaluation of marketing, competitor research, customer satisfaction and customer acquisition initiati

ProductSpecialistSmallCommercial

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

Seasonal Housekeeper (Full-time)

Sentry Insurance · Stevens Point, WI, US · Posted 2026-08-07

Join our detail-oriented housekeeping team that helps maintain the beauty and charm of The Inn at SentryWorld 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 comes delivering excellent service.

SeasonalHousekeeperFull-time

Fitness Attendant

Sentry Insurance · Stevens Point, WI, US · Posted 2026-08-07

Provides customer service support at the Wellness Center front desk by greeting members and providing prompt information to current and prospective members. As a Fitness Attendant at Sentry’s Wellness Center, you will play a critical part in providing health and wellness service to other Sentry Insurance associates. Ho

FitnessAttendant

Bartender

Sentry Insurance · Stevens Point, WI, US · Posted 2026-08-06

Responsible for providing a positive and friendly bar experience. Prepares and provides mixed drinks, beer and wine offerings, as well as full dining service from the restaurant. Our friendly team at PJ’s is looking to add energetic and experienced Bartenders with knowledge of contemporary cocktails, beer, and wine and

Bartender

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

Seasonal Groundskeeper I

Sentry Insurance · Stevens Point, WI, US · Posted 2026-08-04

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

SeasonalGroundskeeper

Associate SEM Analyst

Sentry Insurance · Multiple Locations, US · Posted 2026-08-03 · 1+ years

Our Associate SEM Analysts support paid media initiatives. What You'll Do As an Associate SEM Analyst, you will: - Assist in the day-to-day management and optimization of campaigns on digital marketing platforms. - Conduct keyword research, ad copy creation, and bid management to improve campaign performance. - Monitor

Excel

Seasonal Housekeeper

Sentry Insurance · Stevens Point, WI, US · Posted 2026-07-31

Join our detail-oriented housekeeping team that helps maintain the beauty and charm of The Inn at SentryWorld 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 comes delivering excellent service.

SeasonalHousekeeper

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

Line/Grill Cook at SentryWorld

Sentry Insurance · Stevens Point, WI, US · Posted 2026-07-29 · 0-2 years

Our SentryWorld team is looking to add Line/Grill Cooks to our culinary department. We are looking for people like you who are curious, hardworking, and always looking to improve At Sentry, the best parts of our business come from our very own backyard. All across our organization, we work to cultivate homegrown talent

LineGrillCookSentryWorld

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

Workplace Technology Engineer (Hybrid Work Model)

Sentry Insurance · Multiple Locations, US · Posted 2026-07-15 · 2+ years

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 wit

WorkplaceTechnologyEngineerModel

Account Executive-North Dakota and Minnesota Captive Territory

Sentry Insurance · 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

Internal Auditor

Sentry Insurance · Stevens Point, WI, US · Posted 2026-07-10

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

InternalAuditor

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

Licensed Direct Sales Representative - P&C

Sentry Insurance · Multiple Locations, US · Posted 2026-07-08

Responsible for selling and servicing Sentry products to meet growth, retention, profit and sales objectives for Non-Standard Auto and Personal Lines. This position will be located in either our Stevens Point, WI, Goldsboro, NC, Freeport, IL, or El Paso, TX Office. What You'll Do: As a Personal Lines Sales Agent, you w

LicensedDirectSalesRepresentative

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

Social Media Strategist - Digital Reputation

Sentry Insurance · Stevens Point, WI, US · Posted 2026-07-08 · 3+ years

Join Sentry’s team as a Social Media Strategist – Digital Reputation! What You'll Do As a Social Media Strategist – Digital Reputation, you will: - Continuously track brand mentions, sentiment, and conversations across social media, forums, blogs, review sites, and search results. - Collaborate with departments outside

SocialMediaStrategistDigitalReputation

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

Trial Attorney - In-House Counsel

Sentry Insurance · Remote, Country not listed · Posted 2026-07-07 · 2+ years

As an experienced litigator, you’ll apply your legal skills and experience to represent the interests of Sentry insureds by defending claims made under insurance policies. This position will work primarily remotely from a home office and will require intermittent travel to Northern California to appear in court as nece

TrialAttorneyIn-HouseCounsel