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Sentry Insurance jobs

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

Customer Service Representative

Sentry Insurance · Freeport, IL, US; Goldsboro, NC, US; El Paso, US; Nashville Office, US · Posted 2026-10-05

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

ServiceRepresentativesentrytakeovercareerinsuranceinformation

SEM Analyst

Sentry Insurance · Stevens Point, WI, US · Posted 2026-10-05 · 2+ years

Our SEM Analysts are responsible for driving customer acquisition and lead generation through the planning, execution, and optimization of paid search and digital advertising campaigns. What You'll Do As an SEM Analyst, you will manage search marketing initiatives across platforms such as Google Ads and Microsoft Adver

SEMAnalyst

Software Engineer (Hybrid Work Model)

Sentry Insurance · Stevens Point, WI, US · Posted 2026-10-05

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 resou

SoftwareEngineerModel

Communications Specialist

Sentry Insurance · Nashville, TN, US · Posted 2026-10-05 · 5+ years

Our Communications Specialists are responsible for the operational implementation of corporate communications. What You'll Do - Work collaboratively with and provide communications coaching for strategic leadership team members. - Direct communications support for assigned senior leadership, provides direct support to

CommunicationsSpecialist

Risk Control Consultant-Connecticut

Sentry Insurance · Hartford, CT, US · Posted 2026-10-05 · 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 will conduct comprehensive safety

RiskControlConsultant-Connecticut

Senior Staff Attorney - Insurance Defense

Sentry Insurance · Remote, Country not listed · Posted 2026-10-02 · 7+ years

Use your litigation experience to defend Sentry insureds against claims and represent Sentry in direct policy actions. This position will work primarily remotely from a home office and will require intermittent travel in and around Southern California to appear in court as necessary. What You’ll Do: As a Senior Trial A

AttorneyInsuranceDefense

Risk Control Consultant-North Carolina

Sentry Insurance · North Carolina Remote, Country not listed · Posted 2026-10-01 · 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-NorthCarolina

Senior Financial Analyst-Financial Analysis and Planning

Sentry Insurance · Stevens Point, WI, US · Posted 2026-10-01 · 5+ years

You will have a primary role in assisting corporate areas with staff planning, expense budgeting & tracking, reporting of actual to plan variances, & additional FP&A tasks as assigned. We’re seeking a self-motivated professional with technical and analytical skills to join our Financial Planning and Analysis team as a

FinancialAnalyst-FinancialAnalysisPlanning

Scanning & Distribution Technician- LT20

Sentry Insurance · Stevens Point, WI, US · Posted 2026-09-29

Support Enterprise Scanning & Mail Services by processing incoming/outgoing mail, operating mailroom and imaging equipment, and handling administrative tasks We are looking to add a Scanning and Distribution Tech to our Stevens Point, WI office team! Our Scanning and Distribution Tech provides support to the Enterprise

ScanningDistributionTechnicianLT20

Underwriting Specialist - Middle Market

Sentry Insurance · Denver, CO, US · Posted 2026-09-29 · 5+ years

Applies Underwriting policy, philosophy and procedures to evaluate the acceptability of submitted business. Based on qualifications and experience, this position can be filled at either an Underwriting Specialist or Senior Underwriting Specialist level. What You’ll Do In this role, you will: - Work closely with agency

UnderwritingSpecialistMiddleMarket

Industrial Hygienist Internship Summer 2027

Sentry Insurance · Stevens Point, WI, US · Posted 2026-09-25

In this internship, you'll gain hands-on experience and work with a mentor to learn all about Industrial Hygienist role, and network with leadership at social events. Here at Sentry, we value real work experience for our interns. We offer not only an internship, but an experience for students to get a head start on the

IndustrialHygienistSummer

IT Product Analyst Manager (Hybrid Work Model)

Sentry Insurance · Nashville, TN, US · Posted 2026-09-25 · 5+ years

You’ll play a pivotal role in driving the evolution of our IT products by leveraging your comprehensive understanding of business strategy, technology, and market trends. 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 drive

ProductAnalystModel

Executive Assistant

Sentry Insurance · Stevens Point, WI, US · Posted 2026-09-24 · 3+ years

Our Executive Assistants work closely with our executives to ensure that day-to-day operations run smoothly. In this role, you will oversee impactful projects and become deeply involved in the business. This role performs anticipatory and comprehensive administrative and executive support related tasks for assigned exe

ExecutiveAssistant

Account Executive-Rhode Island and Massachusetts Captive Territory

Sentry Insurance · Multiple Locations, US · Posted 2026-09-24

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-RhodeIslandMassachusettsCaptiveTerritory

Account Executive-Massachusetts Captive Territory

Sentry Insurance · Boston, MA, US · Posted 2026-09-24

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-MassachusettsCaptiveTerritory

Business Product Analyst-Personal Lines

Sentry Insurance · Madison, WI, US; Stevens Point, WI, US · Posted 2026-09-23 · 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-PersonalLinessentryproductssupportinsuranceoffer

Claims Representative - College Co-op 2027

Sentry Insurance · Stevens Point, WI, US · Posted 2026-09-21

As a Claims Co-op, you’ll practice investigation, evaluation, and communication skills while making real impact. Work part-time during school and full-time over breaks. At Sentry, we realize that getting valuable, hands-on experience is important for you and your career. We’re looking to recruit UW-Stevens Point for ou

ClaimsRepresentativeCollegeCo-op

Claims Internship Summer 2027 - El Paso, TX

Sentry Insurance · El Paso, TX, US · Posted 2026-09-18

In this internship, you'll gain hands-on experience and work with a mentor to learn all about the Claims role and network with leadership at social events. Here at Sentry, we value real work experience for our interns. We offer not only an internship, but an experience for students to get a head start on their careers,

ClaimsSummerPaso

Claims Internship Summer 2027 - Nashville, TN

Sentry Insurance · Nashville, TN, US · Posted 2026-09-18

In this internship, you'll gain hands-on experience and work with a mentor to learn all about the Claims role and network with leadership at social events. Here at Sentry, we value real work experience for our interns. We offer not only an internship, but an experience for students to get a head start on their careers,

ClaimsSummerNashville

Claims Internship Summer 2027 - Stevens Point, WI

Sentry Insurance · Stevens Point, WI, US · Posted 2026-09-18

In this internship, you'll gain hands-on experience and work with a mentor to learn all about the Claims role and network with leadership at social events. Here at Sentry, we value real work experience for our interns. We offer not only an internship, but an experience for students to get a head start on their careers,

ClaimsSummerStevensPoint

Host/Hostess at PJ's

Sentry Insurance · Stevens Point, WI, US · Posted 2026-09-17 · 0-2 years

The Host/Hostess is responsible for greeting, welcoming and seating all guests on a timely and courteous basis PJ's at SentryWorld is seeking an energetic and enthusiastic Hosts (Less Than 20 hours and On-call) to join our team. We work as a small team and have very high standards of service, meaning we work hard and w

HostHostess

Actuary Internship P&C Summer 2027

Sentry Insurance · Multiple Locations, US · Posted 2026-09-17

In this internship, you'll gain hands-on experience and work with a mentor to learn all about the Actuarial role and network with leadership at social events. Here at Sentry, we value real work experience for our interns. We offer not only an internship, but an experience for students to get a head start on their caree

ActuarySummer

Event & Meeting Planner

Sentry Insurance · Stevens Point, WI, US · Posted 2026-09-17 · 5+ years

Our Event and Meeting Planners provide effective project management support of meetings and events. What You'll Do - Develop and implements all aspects of small to medium-size events and meeting planning requirements. Work directly with a Lead Planner on tasks pertaining to the event. Ensure timely and effective implem

EventMeetingPlanner

Direct Writer-Program Specialist

Sentry Insurance · Stevens Point, WI, US · Posted 2026-09-16 · 2+ years

Administer specialty insurance programs, service insureds, process requests, and coordinate monthly updates with John Deere. The role will be staffed at our Sentry Home Office in Stevens Point, WI following the hybrid work model. This role is NOT available for remote work. What You'll Do - Respond to a variety of custo

DirectWriter-ProgramSpecialist

Line/Grill Cook II at PJ's

Sentry Insurance · Stevens Point, WI, US · Posted 2026-09-16 · 2+ years

Our PJ's team is looking to add a Full-time Line/Grill Cook II 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 home

LineGrillCook

Accounting Internship Summer 2027

Sentry Insurance · Stevens Point, WI, US · Posted 2026-09-15

In this internship, you'll gain hands-on experience and work with a mentor to learn all about Accounting, and network with leadership at social events. At Sentry, we believe in providing hands-on experience that gives students a head start on their careers. As an Accounting intern, you’ll partner with a dedicated mento

AccountingSummer

Occupational Safety Internship Summer 2027

Sentry Insurance · Stevens Point, WI, US · Posted 2026-09-14

In this internship, you'll gain hands-on experience and work with a mentor to learn all about Risk Control/Occupational Safety, and network with leadership at social events. Here at Sentry, we value real work experience for our interns. We offer not only an internship, but an experience for students to get a head start

OccupationalSafetySummer

Advanced Analytics Modeler (Hybrid Work Model)

Sentry Insurance · Stevens Point, WI, US · Posted 2026-09-14 · 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

Regional Executive

Sentry Insurance · Irvine, CA, US · Posted 2026-09-10 · 10+ years

We’re looking for a strategic, results-driven Regional Executive to take ownership of the revenue and profitability of our $100M+ Pacific region. In this leadership role you will own developing and implementing underwriting strategies across our commercial lines for the Pacific region. You’ll lead a dedicated regional

RegionalExecutive

Door Attendant

Sentry Insurance · Stevens Point, WI, US · Posted 2026-09-09

Responsible for greeting and opening doors for guest upon their arrival and departure from the Inn At the Inn at SentryWorld, we focus on the guest experience. As the Door Attendant, you’ll be the first person our guests meet. With a welcoming demeanor, you’ll welcome and escort our guests and help transport their lugg

DoorAttendant

Outfitter Attendant

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

Oversees outfitter desk providing guests with rentals and recommendations on recreational activities, services, dining, and other local amenities. At the Inn at SentryWorld, we focus on the guest experience. We’re looking for a Full-time Outfitter Attendant, who’ll assist guests with rentals and suggestions on recreati

OutfitterAttendant

Accounting Student Co-op 2027-2028

Sentry Insurance · Stevens Point, WI, US · Posted 2026-09-09

Student finance opportunity across Internal Audit, Treasury Services & Premium Tax Accounting, and Statutory & Income Tax Accounting within Sentry. At Sentry, we are dedicated to cultivating home-grown talent across our organization. We have a unique opportunity for a UW-Stevens Point student to work part-time in the S

AccountingStudentCo-op

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 Project Manager

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 will be located at our office in Stevens Point, WI, Madison, WI, Davenport, IA or El Paso, TX in a hybrid work model and

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

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

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

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 · 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

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

Account Executive- Alabama Captive Territory

Sentry Insurance · Birmingham, 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-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