Jobs at Sentry (sentry.com)

Defend Sentry insureds and the company in insurance claims and direct policy actions. Independently manage litigation caseloads from pleadings through trial, including motion practice, depositions, expert discovery, trial preparation, mediation, arbitration, and settlement. Communicate case strategy and progress to policyholders and claims associates while handling complex matters with minimal supervision. The role is primarily remote and requires intermittent court travel throughout Southern California.

Conduct onsite facility and job-site safety evaluations, assess property and operational risks, and prepare reports supporting underwriting decisions. Advise customers on safety policies, loss prevention, maintenance, fire protection, fleet safety, and regulatory compliance. Deliver OSHA seminars and risk management training, develop service plans, and manage relationships across assigned accounts in North Carolina and Virginia. The role requires substantial field travel, independent territory management, and expertise in OSHA, ANSI, NFPA, and DOT standards.

Supports corporate financial planning through staff planning, expense budgeting and tracking, variance analysis, forecasting, reporting, and financial modeling. Reviews financial statements for accuracy and compliance, advises business leaders, develops corrective actions, and provides recommendations for strategic initiatives. The role also leads finance-related projects, resolves complex issues, supports team members, and improves financial procedures and systems.

Underwrites complex middle-market insurance accounts by evaluating risk, pricing policies, applying underwriting guidelines, coordinating with agencies and internal teams, and referring business beyond authority limits. The role also improves procedures, monitors insurance market developments, trains underwriters, and presents underwriting practices. Candidates need a bachelor's degree or equivalent experience, at least five years of related experience, insurance and reinsurance knowledge, strong analytical and communication skills, and preferably middle-market underwriting experience and industry coursework.

Sell commercial insurance, 401(k), and life insurance products to niche-market businesses across a Massachusetts territory. Responsibilities include growing premium volume, retaining profitable accounts, building customer relationships, pursuing new opportunities, and collaborating with underwriting, claims, loss control, audit, and service teams. The role is home-office based with regular field travel and requires residence within the assigned territory.

Sell commercial insurance, 401(k), and life insurance products to niche-market businesses across Rhode Island and Massachusetts. Responsibilities include growing premium volume, retaining profitable accounts, building business relationships, pursuing territory opportunities, generating new sales through existing relationships, and collaborating with underwriting, claims, loss control, audit, and customer service teams. The role is remote with a home office and regular travel throughout the assigned territory.

Provides comprehensive executive and administrative support, including complex calendar and travel coordination, meeting and event logistics, confidential information management, communications, reports, presentations, and special project tracking. Partners with executives, anticipates needs, coordinates stakeholders, and ensures initiatives and board-level preparations meet milestones. Requires strong organization, judgment, communication, accuracy, confidentiality, and proficiency with Microsoft Office and workplace productivity tools.

Supports personal lines insurance product development by documenting and filing products with state Departments of Insurance, researching competitors and product performance, coordinating rate and rule revisions, collaborating with business partners, and implementing underwriting rules in systems. The role may also support new product launches, market expansion, process improvements, and reporting.

Insurance claims intern gains hands-on experience reviewing policies, verifying coverage, investigating losses, gathering documentation, maintaining records, supporting negotiations and settlements, and guiding customers through the claims process. The role includes mentorship, leadership networking, hybrid work, and professional development opportunities.

Claims internship providing hands-on experience with negotiations, settlements, customer guidance, policy and coverage review, loss investigations, documentation, and claims recordkeeping. Interns receive mentorship, leadership networking, and hybrid work experience while developing critical thinking, decision-making, collaboration, empathy, and organizational skills.

This internship provides hands-on experience in insurance claims, including claims negotiations, settlement processes, customer guidance, policy and coverage review, loss investigation, documentation analysis, and maintaining detailed records. Interns receive mentorship, leadership networking opportunities, and exposure to a professional corporate environment. The role is hybrid in Nashville and includes housing, parking, technology, and potential meal support.

Actuarial interns gain practical experience in property and casualty insurance through mentorship, project work, data compilation, statistical analysis, rate adequacy monitoring, corporate risk management, and loss and expense reserve evaluation. Interns also learn company systems, operations, and actuarial methodologies while participating in networking and professional development activities. The role is hybrid in Madison or Stevens Point, Wisconsin.

Accounting interns gain hands-on experience across Finance teams by preparing financial statement exhibits, reviewing and reconciling statements to general ledger data, assisting with report automation, verifying transaction accuracy, troubleshooting reconciliation issues, and supporting accounting processes and systems. The internship includes mentorship, leadership networking, team projects, and a hybrid work schedule.

Gain hands-on experience in risk control and occupational safety by partnering with safety consultants, conducting workplace inspections, preparing technical reports, evaluating insurance risks, and advising customers on workplace safety. The internship includes mentorship, networking, hybrid work, and exposure to multiple insurance lines and business units.

Leads revenue, profitability, underwriting strategy, premium growth, and operational excellence for a $100M+ Pacific commercial insurance region. Manages more than 20 professionals, develops underwriting standards, supports field underwriters, guides agency marketing execution, analyzes market and competitor trends, and collaborates with senior leadership on profitable regional growth.

Lead and grow a new Hawaii commercial lines book of business by developing market strategy, positioning products to increase premium and profitability, soliciting accounts via independent agents, evaluating and underwriting risks, monitoring results and loss ratios, and building and managing a small underwriting team to achieve regional goals.

Sell specialized commercial insurance, 401(k), and life insurance products to niche-market businesses across a Missouri territory. Responsibilities include acquiring new accounts, retaining profitable business, building client relationships, pursuing territory opportunities, and collaborating with underwriting, claims, loss control, audit, and customer service teams. The role is remote, territory-based, and requires obtaining and maintaining P&C and life insurance licenses, a valid driver’s license, and travel availability.

Sell specialized commercial insurance, 401(k), and life insurance products to niche-market businesses across an Ohio and West Virginia territory. Responsibilities include acquiring and retaining profitable accounts, building business relationships, pursuing territory opportunities, leveraging existing customers for growth, and collaborating with underwriting, claims, loss control, audit, and customer service teams. The role is remote, territory-based, and requires licensing, travel, and residence within the sales territory.

The Account Executive sells specialized insurance products, builds relationships with clients, and retains profitable business in assigned territories.

Manage a team of middle market commercial lines underwriters, oversee day-to-day operations, provide technical guidance, improve productivity and profitability, interpret underwriting guidelines for complex files, handle difficult inquiries, coordinate training, and collaborate with cross-functional teams to develop business relationships.