Jobs at Sentry (sentry.com)

Sell commercial insurance, 401(k), and life insurance products to niche-market businesses across Rhode Island and Massachusetts. The Account Executive develops new business, retains profitable accounts, builds customer relationships, and collaborates with underwriting, claims, loss control, audit, and customer service teams. This remote, territory-based role requires regular field travel, residence within the assigned territory, a valid driver’s license, and the ability to obtain and maintain required insurance licenses.

Performs FP&A activities including staff planning, expense tracking, actual-to-plan variance analysis, financial reporting, budgeting support, compliance monitoring, and ad hoc analysis. Advises managers on financial results and corrective actions, collaborates with business stakeholders on strategic initiatives, resolves complex issues, and communicates recommendations to management.

Manages motorcycle dealership relationships across a large territory to grow insurance sales and premium. Responsibilities include dealership training, product and claims expertise, prospecting, complaint handling, event promotion, lead-source development, branding opportunities, sales planning, and partnership development with Finance & Insurance and Service departments. The role requires frequent dealer engagement, motorcycle industry familiarity, insurance knowledge, travel, licensing eligibility, and strong communication and sales skills.

Designs and develops learner-centered experiences across e-learning, instructor-led, blended, immersive, and performance-support formats. Conducts needs assessments, creates multimedia learning assets, applies UX and adult learning principles, manages projects using Agile methods, and evaluates learning impact through data analytics. Requires collaboration with subject matter experts, proficiency in instructional design and authoring tools, multimedia production, and the ability to deliver hybrid, virtual, and in-person learning solutions.

Designs intuitive digital experiences through user research, usability testing, wireframes, prototypes, responsive designs, and design systems. Collaborates with IT, marketing, and business stakeholders to translate requirements into user-centered solutions. Presents design rationale, maintains design integrity, performs acceptance testing, applies accessibility standards, and uses AI tools to improve UX workflows.

Drives sales for SentryWorld’s golf, wedding, dining, hotel, catering, and event venues. Responsibilities include prospecting, developing customer relationships, negotiating group and catering business, preparing quotes, closing sales, attending networking events, tracking sales activity, supporting promotional initiatives, and reporting on market opportunities. Requires strong communication, analytical, negotiation, prospecting, revenue management, and customer-service skills, along with a bachelor’s degree or equivalent experience and at least two years of related experience.

Investigate and resolve complex commercial liability insurance claims. Responsibilities include reviewing coverage, evaluating liability and damages, taking statements, analyzing exposures, setting reserves, negotiating settlements, managing litigated and non-litigated bodily injury claims, coordinating with legal counsel and service providers, and maintaining regulatory and policy-compliant documentation.

Manage non-attorney-represented bodily injury auto claims by verifying coverage, investigating liability, reviewing evidence, setting reserves, negotiating settlements, resolving coverage and damage issues, documenting decisions, ensuring regulatory compliance, and providing empathetic customer service. The role requires maintaining state licensing, analyzing insurance policies and regulations, prioritizing caseloads, and making timely claim decisions.

Sell specialized commercial insurance, 401(k) and life products across Montana and northern Wyoming. Build and retain profitable niche-market accounts, collaborate with underwriting and claims, leverage relationships for new business, and provide quality service while meeting sales objectives and compliance.

Sell commercial insurance, 401(k), and life insurance products to niche-market businesses across the New York territory. Responsibilities include acquiring and retaining profitable accounts, building client relationships, pursuing territory opportunities, generating referrals, and collaborating with underwriting, claims, loss control, audit, and customer service teams. The role is home-office based with regular field travel and requires maintaining relevant insurance licenses and a valid driver’s license.

Investigate and resolve liability insurance claims by verifying coverage, evaluating liability and damages, reviewing evidence and medical documentation, setting reserves, negotiating settlements, and ensuring regulatory compliance. The role manages an independent caseload, documents claim decisions, communicates empathetically with customers and stakeholders, and maintains required state licensing.

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.

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.

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.

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.

Sell specialized commercial insurance, 401(k), and life products to niche market accounts in a defined territory. Build and maintain client relationships, retain profitable business, pursue new sales opportunities, and coordinate with underwriting, claims, loss control, audit, and customer service. Work remotely from within the territory and meet travel and driving requirements.