Jobs at Sentry (sentry.com)

Sell specialized commercial insurance, 401(k), and life products to niche market accounts in a defined territory. Prospect and retain profitable business, build relationships, coordinate with underwriting/claims/loss control/audit/customer service, meet sales objectives, maintain required licenses, and travel within the territory.

Serve as the organization's government affairs expert and liaison, develop and execute state and local advocacy strategies, build relationships with legislators, regulators, and trade associations, manage outside lobbyists, represent the company to policymakers, and communicate policy impacts to internal stakeholders.

Serve as the field-office HR representative supporting managers and associates in associate relations, investigations, terminations and exit interviews; execute full-cycle recruiting; coach managers on corrective action and communications; and deliver HR programs in performance, compensation, career and leadership development.

Manage a caseload of complex commercial liability and auto claims, including litigation. Investigate coverages, obtain statements and reports, negotiate settlements within authority, coordinate with defense counsel, document decisions, and provide technical training to the claims team.

Investigate and manage commercial liability insurance claims independently, evaluate coverage and liability, negotiate settlements, set reserves, work with counsel and vendors, and document decisions for litigated and non‑litigated cases.

The Account Executive sells specialized commercial insurance and retirement products, builds relationships with clients, and provides ongoing service to retain business.

Account Executives sell specialized insurance products, building relationships with clients and managing accounts to achieve sales objectives.

The Territory Executive manages broker and client relationships, generates submissions, collaborates with underwriting, and presents sales proposals for Workers Compensation accounts.

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

Perform daily treasury and investment accounting tasks including cash positioning, wires, reconciliations, trading validations, reporting, audit support, system maintenance, and process improvements to automate and enhance data quality.

Lead and manage a team of middle-market underwriters, oversee day-to-day underwriting operations, interpret guidelines for complex files, drive productivity and profitability improvements, provide technical guidance and training, handle difficult inquiries, and collaborate cross-functionally to develop agency and insured relationships.

As a Senior Trial Attorney, you'll represent Sentry and insured clients by defending claims, handling all aspects of litigation, and managing a full caseload with minimal oversight.

Account Executives sell specialized commercial insurance and related products while building relationships with clients and achieving sales objectives.

Account Executives sell commercial insurance, manage client relationships, and increase premium volume in the New York and Connecticut territory.

The Account Executive sells specialized commercial insurance, 401K, and life insurance products, builds relationships, and provides quality service to clients in their territory.

The Risk Control Consultant conducts safety assessments, develops safety policies and training, and advises clients on risk management to minimize exposure to losses.

The Senior Actuarial Analyst supports pricing and actuarial analysis for the Small Commercial insurance portfolio, collaborating on data validation, rate filings, and product recommendations.

The Account Executive sells specialized insurance products, retains business, builds relationships, and pursues market opportunities within a defined territory.

Serve as primary contact for producers, customers, and agents to manage assigned commercial accounts—handling service requests, quotes, renewals, policy changes, billing, audits, and underwriting coordination while identifying placement opportunities and building relationships.

The Corporate and Transactional Paralegal reviews and negotiates legal agreements, manages trademark portfolios, assists with M&A due diligence, and ensures regulatory compliance.