Cycle Dealership Sales Specialist

Sentry Insurance is seeking a Cycle Dealership Sales Specialist to grow and manage relationships with cycle and powersports dealerships. In this role, you'll promote tailored commercial insurance and finance solutions that help dealers manage risk and protect their businesses. You'll prospect and onboard new dealerships, conduct onsite visits, deliver product presentations, and partner closely with underwriting and claims teams. At Sentry, you'll join a stable, collaborative culture with strong support for learning, competitive pay and benefits, and clear opportunities to advance your sales and insurance career nationwide.

Responsibilities

• Build and manage relationships with cycle and powersports dealerships in assigned territory
• Recommend tailored insurance and finance solutions to dealership owners and managers
• Meet or exceed sales and profitability targets for assigned accounts
• Conduct onsite visits, presentations, and product education for dealership staff
• Collaborate with underwriting, claims, and support teams to deliver seamless service
• Monitor market trends and competitor offerings to refine sales strategies
• Maintain accurate CRM records, pipelines, and sales forecasts
• Represent Sentry at industry events, trade shows, and dealer meetings

Required Skills

• B2
• B sales
• Territory management
• Insurance product knowledge
• Negotiation
• Prospecting and lead generation
• CRM software
• Presentation skills
• Financial analysis basics
• Contract review
• Account management