Sentry
Our associates are the most important part of our company.


We became one of the most financially strong mutual insurance companies in the U.S. by striving to provide the best possible service to our business customers. We do this by having conversations, forming relationships, and getting to know the people we work with and their businesses.

We make that same commitment to our associates. When you join Sentry, we don’t just want you to perform tasks each day. We want you to enjoy your time with us. You’re in the driver’s seat of your career path here—sharing feedback, creating goals, accessing professional development resources, and identifying how you can contribute to both your success and the success of the company.

Yes, we work hard. But we work with the purpose of helping others, and with the understanding that there’s more to life than work. We invite you to learn more about us. You’ll find we’re much more than insurance.

10/20/2026  
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, and insightful when it comes to delivering excellent service. If you enjoy forming long-lasting connections join our Front Desk team. As our Full-time Front Desk Attendant , we’ll count on you to create an exceptional first impression and luxury experience for all our guests What You’ll Do As a Front Desk Attendant, you will: Provide guests with a friendly and efficient check-in confirming guest information, verifying room rate, selecting room, coding electronic keys, providing welcome packet, and providing directions to room. Provide detailed and accurate information in person or over the phone regarding hotel policies, services, amenities, and...
Sentry Stevens Point, WI Full Time
10/20/2026  
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 manage complex material damage appraisals for claims specific to agricultural equipment that typically have high loss exposures. Adhere to state-specific compliance issues for assigned jurisdictions. Evaluate losses and prepare or audit a damage appraisal, estimating the repairs needed for items such as labor costs, actual cash value, calculations, parts, and repairs prices. Conduct equipment damage re-inspections of staff and independent appraisers to ensure accuracy and resolve any conflicts arising from the original inspection. Review documentation of total loss estimates to determine if equipment is repairable. Review, monitor, and control...
Sentry Stevens Point, WI Full Time
10/20/2026  
Supports the operational needs of the 401k line of business. What You’ll Do As an Operations Support Technician – 401K associate you will… Process transactions and facilitates plan/customer data management validating client data and funding while maintaining and creating participant census data. Respond to questions from customers, producers, and supporting units. Prepares, maintains, reviews, and analyzes plan documents and electronic records ensuring that each customer plan administration is compliant according to the plan document. Collaborates with other 401K units to meet client needs while providing sales support from point of sale to ongoing plan administration. Supports operations and service teams with quality audits, system testing, and document internal procedures as well as assisting with onboarding and informal training for new associates. What it Takes High school Diploma or equivalent work experience Excellent verbal and written communications...
Sentry Stevens Point, WI Full Time
10/16/2026  
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 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 appropriate resolution...
Sentry Stevens Point, WI Full Time
10/16/2026  
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 the policies and interpreting policy terms, conditions and language. Evaluate liability by taking recorded statements, reviewing police reports, and compiling other pertinent evidence. Negotiate or deny liability based on the investigation outcome. Set appropriate claim reserves in a timely manner based on ongoing evaluations of liability. Negotiate settlements with policyholders, claimants, and other insurance carriers to reach fair resolutions within established guidelines. Ensure claims are paid promptly and within authorized limits. Ensure compliance with industry regulations, legal requirements, and internal policies by thoroughly documenting all...
Sentry El Paso, TX Full Time
10/16/2026  
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/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...
Sentry Stevens Point, WI Full Time
10/15/2026  
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 recruiting process - this is a highly visible role in which you’ll be able to network and develop quality applicant pools as you help attract top talent to Sentry.   What You'll Do As a Talent Acquisition Specialist, you will: Manage the entire recruitment cycle for positions from workforce planning needs, through the requisition process, the presentation of candidates, and pre-hire screens to final offer letters. Collaborate with hiring managers to understand job requirements and competencies, evaluates and identify staffing strategies to develop talented candidate pools and set expectations. Develop and maintain a strong relationship with all candidates to keep...
Sentry Stevens Point, WI Full Time
10/14/2026  
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, and other key performance indicators. Analyzes findings to detect trends, uncover insights, identify barriers, and highlight opportunities. Monitors organic search performance using Google Search Console, analytics platforms, SEO tools, automated site audits, and other available data sources. Identifies meaningful changes and investigates potential causes and implications. Reviews automated crawl reports, platform notifications, and SEO health signals to identify emerging issues. Assesses potential impact and urgency, escalating material technical concerns to Technical SEO and incorporating lower-priority findings into ongoing reporting and...
Sentry Nashville, TN Full Time
10/13/2026  
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 position is...
Sentry St. Louis, MO Full Time
10/13/2026  
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 escalation point in the event of a cybersecurity incident. You will also maintain security playbooks and incident resolution procedures to ensure accuracy and consistency in the handling of security matters. You'll also lead and/or participate in complex projects within the security team. You will play a key role in the creation and analysis of metric reports to support the security program. You will also develop, implement and maintain security tools and platforms utilized by the Security Operations Center.  This position will be located at our Office in Stevens Point, WI in a hybrid work model and is not a fully remote opportunity. Sentry does not offer employment...
Sentry Stevens Point, WI Full Time
10/12/2026  
We're seeking a high performing, goal driven Powersports and Motorcycle Sales Manager to lead new business growth in our Powersports division. This role focuses on developing and managing relationships with specialty and independent insurance agents as well as affinity groups, driving profitable growth and expanding market presence.   The ideal candidate is a competitive self-starter who thrives working independently, consistently exceeds sales goals, and knows how to build strategic partnerships that deliver results. The exact territory for this role will be decided based on the location of the individual selected for the opportunity.   What You’ll Do   As the Powersports and Motorcycle Sales Manager, you will prospect, develop and maintain motorcycle focused accounts for new business production.  Additionally, you will:   Manage the assigned US territory and/or have areas of responsibility assigned that are countrywide such as new business development of...
Sentry Madison, WI Full Time
10/12/2026  
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 comprehensive safety and risk management assessments, provide our Underwriting teams with a strong analytical opinion of risk to support our goal of profitable growth within variety of middle to large premium market segment for Dealerships, Construction, Manufacturing, Wholesale Trade, Retail, Commercial Real Estate and Service industries.  In addition, the successful candidate will develop close relationships with our agents and policyholders, conducting selected safety seminars and training, to build the value-added service that Sentry is known for.   The ideal candidate's preferred location would be in or around the metro-Charlotte, NC area with good access to major...
Sentry Charlotte, NC Full Time
10/12/2026  
As a GRC Analyst, you’ll test security controls, assess risk and compliance, report findings to stakeholders, and maintain information security policies and standards. You'll participate in information security risk management by testing the effectiveness of security controls, assessing security controls and compliance for suppliers, systems, and processes against threats and industry best practices to confirm adherence to security and compliance requirements. You'll report findings and recommendations to information security management and business stakeholders to ensure any concerns are resolved. You'll also review and maintain ongoing governance of the organization's information security policies and standards. This position will be located at our Office in Stevens Point, WI in a hybrid work model and is not a fully remote opportunity. Sentry does not offer employment in this position to holders of F-1, J-1, and H-1 Visas for the purpose of obtaining practical...
Sentry Stevens Point, WI Full Time
10/12/2026  
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 luggage to and from their accommodations .      What You'll Do   Gre e t and open doors for guests upon their arrival to The Inn at SentryWorld.   T ransport guest’s luggage to and from their vehicles, rooms, and bell attendant station upon arrival/departure.    Promote SentryWorld amenities to help e nsure a positive guest experience.   Maintains working knowledge of Sentry Services facilities and hours of operation, as well as local information to respond to guest questions     What it Takes   Age requirement of 18+...
Sentry Stevens Point, WI Part Time
10/12/2026  
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 driver’s seat of your career path with access to resources to help you succeed personally and professionally.   We’re looking for a strategic leader to guide a team of IT business analysts, who serve as the critical connection point between business partners and technical delivery teams. In this role, you’ll manage a diverse portfolio of work, align project priorities with broader IT strategies, and ensure the delivery of exceptional products. If you excel at seeing the big picture, fostering cross-functional teamwork, and coaching analysts to reach their full potential, this may be the opportunity for you. What You’ll Do You’ll be a valuable contributor to our...
Sentry Nashville, TN Full Time
10/12/2026  
Join Sentry’s team as a Social Media and Community Strategist! What You'll Do As a Social Media & Community Strategist, you will: Develop and enhance workflows for the execution of social media strategies by the Social Media Analysts. Assist Social Media Analysts with the development of social media paid and organic campaign pushing beyond the bounds of tactical execution. Research competition, benchmarks and provides ideas for continuous improvement across social media platforms, networks, and digital communities. Audit current social media processes and explores the use of automation to gain efficiencies, achieve outcomes more quickly, and expand on social media initiatives. Evaluate current use of social media tools and technologies and recommends changes to increase efficiency. Partner with the Social Media Manager to develop UGC strategies and automated reporting against established social media KPIs for social media initiatives, campaigns, and strategies....
Sentry Stevens Point, WI Full Time
10/09/2026  
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: • Responsible for transporting guests, associates, visitors, and clients to and from The Inn or special trips and deliveries as requested. This may require waiting for extended periods of time for passengers while they attend events • Maintain vehicle records on the shuttle usage (i.e. mileage, gas supply, etc.) and be responsible for keeping the shuttle vehicles clean. • Assist guests with lifting and carrying baggage on and off the shuttle What it Takes • High School Diploma or equivalent work experience. • 0-2 years of related work experience preferred • Clean driving record and a valid driver’s license • Demonstrated ability to be responsible,...
Sentry Stevens Point, WI Part Time
10/08/2026  
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 position is...
Sentry MT Full Time
10/06/2026  
Investigate and resolve litigated claims in an efficient and accurate manner- negotiate settlements, and communicate effectively with policyholders, vendors, and other stakeholders. What You’ll Do: As a Claims Representative Specialist on our PL – Litigation team, you'll provide prompt claims investigation, evaluation, and settlement or denial of litigated claims. In addition, you will: Verify coverages through investigation and reviewing policy terms, conditions, and language. This may require working with coverage counsel in filing declaratory/summary judgements. Evaluate liability by taking recorded statements from involved parties and witnesses and reviewing police reports accident scene photos and other pertinent evidence. Negotiate claims settlements with claimants and their legal representation within assigned authority limits. Comply with industry regulations, legal requirements, and internal policies through thorough documentation of all decisions correspondence...
Sentry Nashville, TN Full Time
10/06/2026  
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, conditions and language. Evaluate liability by taking recorded statements, reviewing police reports, and compiling other pertinent evidence. Negotiate or deny liability based on the investigation outcome. Evaluate physical damage and bodily injury claims based on estimates, photos, appraisals, medical reports, medical bills, and other evidence. Working closely with medical providers, repair shops and/or contractors to facilitate necessary and related services. Set appropriate claim reserves in a timely manner based on ongoing evaluations of liability. Negotiate bodily injury settlements with policyholders, claimants, attorneys, and other insurance...
Sentry Goldsboro, NC Full Time