Commercial Insurance Territory Sales Executive

Sentry Insurance is seeking an Account Executive to grow our captive commercial insurance business across Montana and Wyoming. In this field-based role, you'll prospect and develop mid-market business accounts, build strong broker and captive relationships, and deliver tailored property, casualty, and employee benefit solutions. You'll manage a multi-state territory, travel to meet clients, and collaborate closely with underwriting and service teams. Sentry offers competitive pay, comprehensive benefits, and strong career growth in a stable, values-driven organization.

Responsibilities

• Develop and execute a strategic sales plan for the Montana and Wyoming captive territory.
• Prospect, qualify, and close commercial insurance opportunities with mid-market businesses.
• Build and manage relationships with brokers, agents, and captive program partners.
• Conduct needs analyses and deliver tailored insurance and risk management solutions.
• Manage a robust sales pipeline and maintain accurate CRM data and forecasts.
• Collaborate with underwriting, claims, and service teams to support account onboarding and retention.
• Prepare and deliver sales presentations, proposals, and renewal strategies.
• Monitor market trends and competitor activity within the territory.
• Travel regularly throughout the assigned territory to meet with prospects and clients.
• Meet or exceed sales, revenue, and profitability targets aligned with Sentry's goals.

Required Skills

• B2
• B insurance sales
• Territory management
• Commercial P&C insurance knowledge
• Prospecting and lead generation
• Pipeline and CRM management
• Consultative/solution selling
• Contract negotiation
• Account management and retention
• Forecasting and reporting
• Travel and time management