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Sentry Insurance jobs

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

User Experience Designer

Sentry Insurance · Stevens Point, WI, US · Posted 2026-10-30 · 2+ years

As a User Experience (UX) Designer at Sentry, you’ll deliver design solutions for digital experiences that align with our strategic goals and user needs. You’ll partner closely with IT and marketing to translate research, user feedback, and business requirements into intuitive solutions—from wireframes and prototypes t

UserDesigner

SIU Desk Investigator

Sentry Insurance · Goldsboro, NC, US; Nashville, TN, US · Posted 2026-10-29 · 4+ years

This position will be seated at our office Nashville, TN or Goldsboro, NC locations. - As an SIU Desk Investigator, you will conduct basic to moderately complex claims investigations on potentially suspect/inflated auto, workers’ compensation, and commercial claims which may include but is not limited to compiling and

SIUDeskInvestigator

Project Manager (Hybrid Work Model)

Sentry Insurance · Stevens Point, WI, US · Posted 2026-10-29 · 5+ years

Sentry’s Project Managers manage department specific projects and portfolio initiatives. This position can be filled as a Project Manager or Program Manager based on the experience and qualifications of the selected candidate. What You'll Do As a Project Manager, you will: - Deliver department-level projects or assist

ProjectModel

Sales Manager-SentryWorld

Sentry Insurance · Stevens Point, WI, US · Posted 2026-10-28 · 2+ years

Seeking an experienced Sales Manager to drive multi-venue sales across SentryWorld, Sentry Services, and the Inn—from golf and weddings to dining and events You’re a people person, and we’re a people-business. At SentryWorld, we care about our associates – and we encourage our team to bring that same commitment to our

SalesManager-SentryWorld

Operations Technician Senior - Commercial Lines

Sentry Insurance · Stevens Point, WI, US · Posted 2026-10-27

This position will be filled working out of the Stevens Point, WI Strongs office. 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/d

OperationsTechnicianCommercialLines

Customer Service Supervisor

Sentry Insurance · El Paso, TX, US · Posted 2026-10-27 · 5+ years

Supervises a team that provides customer service to a variety of clients. What You’ll Do The ideal Customer Service Supervisor have effect leadership skills and is able to provide direction and motivation to their staff to ensure Sentry continues to provide exceptional customer service. You’ll do this by: - Developing

ServiceSupervisor

Claims Representative Senior - Commercial Liability

Sentry Insurance · Nashville, TN, US; Stevens Point, WI, US · Posted 2026-10-26 · 3+ years

Investigate and resolve insurance claims in an efficient and accurate manner. You’ll independently manage a caseload, negotiate settlements, and communicate with all parties. What You’ll Do: As a Senior Claims Representative on our Commercial Lines - Liability teams, you'll provide superior service by conducting prompt

ClaimsRepresentativeCommercialLiability

Operations Technician Senior - Commercial Lines

Sentry Insurance · Stevens Point, WI, US · Posted 2026-10-26

This position will be filled working out of the Stevens Point, WI Strongs office. 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/d

OperationsTechnicianCommercialLines

Claims Rep Entry Level-Motorcycle

Sentry Insurance · Davenport, IA, US · Posted 2026-10-23

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 requires a learning nature, empathy and interpersonal skills along with a strong desire to assist custo

ClaimsRepEntryLevel-Motorcycle

Account Specialist

Sentry Insurance · El Paso, US · Posted 2026-10-23 · 2+ years

This role will work standard hours of Monday - Friday from 9 AM - 5:30 PM MST. This role will follow Sentry's hybrid work model and will be based out of our El Paso, TX office. As an Account Specialist with Sentry, you’ll serve as a relationship builder to customers and internal partners to develop positive relationshi

AccountSpecialist

Customer Service Representative

Sentry Insurance · Freeport, IL, US; Goldsboro, NC, US; El Paso, US · Posted 2026-10-23

Provide quality customer service via phone, email, and chat in a contact call 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 g

ServiceRepresentative

Front Desk Attendant

Sentry Insurance · Stevens Point, WI, US · Posted 2026-10-20 · 1+ years

In this role, you will provide exceptional service to all guests at The Inn at SentryWorld 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,

FrontDeskAttendant

Ag and Heavy Equipment Appraiser

Sentry Insurance · Stevens Point, WI, US · Posted 2026-10-20 · 5+ years

As an agriculture equipment claims expert, you’ll oversee physical damage claims to control loss expenses and ensure quality and cost-effectiveness This position will be staffed at our Stevens Point, WI office following the hybrid work model. This role is NOT available for remote work. What You'll Do - Supervise and/or

HeavyEquipmentAppraiser

Claims Representative Liability-NARBI

Sentry Insurance · El Paso, US; Stevens Point, WI, US; Davenport, IA, US; Madison, WI, US; Nashville Office · Posted 2026-10-16 · 1+ years

Manage a caseload, investigate liability, negotiate settlements, and resolve coverage, negligence, and damage issues accurately. This position will be handing Non-Attorney Represented Bodily Injury Auto Claims: What You'll Do As a Claims Representative - Liability, you will: - Verify coverage by thoroughly reviewing th

ClaimsRepresentativeLiability-NARBI

Operations Technician Senior - Commercial Lines

Sentry Insurance · Stevens Point, WI, US · Posted 2026-10-16

This position will be filled working out of Sentry's Stevens Point, WI Strongs office. 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 accepta

OperationsTechnicianCommercialLines

Operations Technician Sr. - Transportation & Regional

Sentry Insurance · Stevens Point, WI, US · Posted 2026-10-16

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/de

OperationsTechnicianSrTransportationRegional

Talent Acquisition Specialist

Sentry Insurance · Stevens Point, WI, US · Posted 2026-10-15 · 2+ years

Do you want to join an organization with challenging work assignments where you can build rewarding relationships and make a significant impact on the company’s future? Join the Sentry team as a Talent Acquisition Specialist! In this role, your primary focus will be Talent Acquisition and managing the full-cycle recrui

TalentAcquisitionSpecialist

SEO Analyst

Sentry Insurance · Nashville, TN, US; Stevens Point, WI, US · Posted 2026-10-14 · 3+ years

The SEO Analyst uses data reporting skills to design and deliver performance reporting and SEO dashboards to aid in trend identification and opportunities for conversion increase. What You'll Do - Develops standard and ad hoc SEO/AEO reports and dashboards to measure organic visibility, traffic, engagement, conversion,

SEOAnalyst

Security Operations Center Tier II Analyst

Sentry Insurance · Stevens Point, WI, US · Posted 2026-10-13 · 2+ years

As a Security Operations Tier 2 Analyst, you'll investigate, resolve, and report on escalated security events to protect the organization from potential threats. You'll consult and collaborate with senior team members regarding complex security alerts, escalating the alert if appropriate. You will serve as an escalatio

SecurityOperationsCenterTierAnalyst

Shuttle Driver

Sentry Insurance · Stevens Point, WI, US · Posted 2026-10-09 · 0-2 years

We are looking an On-Call Shuttle Driver to provide transportation throughout the Stevens Point and Central Wisconsin area for our guests during their stay. We are looking for a Shuttle Driver during the hours of 7am-3pm CST and 3pm-11pm CST What You'll Do As a Shuttle Driver for The Inn at SentryWorld, you will: • Res

ShuttleDriver

Account Executive - New York Captive Territory

Sentry Insurance · Syracuse, NY, US; Rochester, NY, US · Posted 2026-10-06

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

AccountExecutiveYorkCaptiveTerritory

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

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, CA, US · 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 · Charlotte, NC, US; VA, US · 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 Planning and Analysis

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-FinancialPlanningAnalysis

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

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

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

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

Claims Representative - Liability

Sentry Insurance · Goldsboro, NC, US; Madison, WI, US; Nashville, TN, US; Stevens Point, WI, US; El Paso, US; Davenport, IA, US; FL, US · Posted 2026-09-15 · 1+ years

You will investigate and resolve insurance claims with a focus on accuracy, efficiency, and fair resolution and independently manage caseloads and negotiate settlements. What You'll Do As a Claims Representative-Liability, you will: - Verify coverage by thoroughly reviewing the policies and interpreting policy terms, c

ClaimsRepresentativeLiability

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

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

Motorcycle Dealership Sales Manager

Sentry Insurance · Madison, WI, US; US, Azerbaijan; Denver, CO, US; Atlanta, GA, US · Posted 2026-08-31 · 3+ years

As a Motorcycle Dealership Sales Manager, 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 d

MotorcycleDealershipSales

Retirement Plan Project Manager

Sentry Insurance · Stevens Point, WI, US; Denver, CO, US; El Paso, TX, US; Davenport, IA, US; Madison, WI, 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, El Paso, TX, or Denver, CO in a hybrid w

Excel

Account Executive-Missouri Captive Territory

Sentry Insurance · St. Louis, MO, US; 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

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

Workplace Technology Engineer (Hybrid Work Model)

Sentry Insurance · Stevens Point, WI, US; Madison, WI, 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

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

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