Cycle Dealership Sales Specialist

Sentry Insurance is seeking a Cycle Dealership Sales Specialist to grow finance and insurance solutions with cycle and powersports dealers. In this role, you'll build strong dealership relationships, conduct consultative needs assessments, and position tailored coverage that supports both dealers and their customers. You'll train and coach dealership teams on Sentry products, drive new business and retention, and collaborate with underwriting, claims, and marketing. Join a stable, integrity-driven company offering strong benefits, development opportunities, and a collaborative culture focused on long-term customer partnerships.

Responsibilities

• Develop and manage relationships with cycle and powersports dealerships in assigned territory
• Promote Sentry Insurance finance and insurance solutions to dealership leadership and sales teams
• Conduct consultative needs assessments to match dealership and customer needs with appropriate coverage
• Deliver product training, sales support, and coaching to dealership staff
• Meet or exceed sales, retention, and profitability goals for assigned accounts
• Collaborate with underwriting, claims, and marketing to support dealer programs and campaigns
• Monitor market trends and competitor offerings to refine sales strategies
• Ensure compliance with regulatory, underwriting, and company guidelines
• Maintain accurate account plans, pipelines, and activity records in CRMRepresent Sentry Insurance at industry events, dealer meetings, and trade shows

Required Skills

• B2
• B sales
• Automotive or powersports dealership knowledge
• Insurance product knowledge (commercial and F&I)
• Account management
• Consultative selling
• Territory management
• CRM software proficiency
• Presentation and training delivery
• Contract negotiation
• Market and competitive analysis