Cycle Dealership Sales Specialist

As a Cycle Dealership Sales Specialist at Sentry, you will drive profitable premium growth by engaging motorcycle dealers with Sentry’s motorcycle insurance products. You will manage a large geographic territory within the Central U.S., building and maintaining strong relationships with dealers to achieve sales and premium objectives.

• Coordinate and lead motorcycle dealership training, relationship management, complaint handling, prospecting and communication within your territory.
• Promote product and brand at assigned motorcycle events to identify and develop new production sources.
• Provide insurance product expertise and lead training efforts for dealerships and affinity associations.
• Deliver comprehensive motorcycle product and claims guidance to dealerships to increase production.
• Develop and maintain strong partnerships with dealership finance, insurance, and service departments to foster service levels and profitable business.
• Develop new and enhance existing dealership quote/lead sources to achieve sales and premium targets.
• Identify, create and execute branding opportunities at the dealership level.
• Implement plans and programs that contribute to dealer‑produced sales and premium objectives.
• Provide product management recommendations for specific product changes using industry knowledge and dealer feedback.

• Associate degree or equivalent work experience; bachelor’s degree preferred.
• 3+ years of related experience in the insurance industry with familiarity of motorcycle dealership operations and departments.
• Basic knowledge of motorcycles preferred.
• Effective communication and human‑relations skills to connect with dealers and customers.
• Sales experience and knowledge of professional sales techniques, including presentation skills.
• Ability to travel 50‑75% within the assigned territory.
• Acceptable motor‑vehicle record and valid driver’s license.
• Property & casualty insurance license preferred; otherwise, ability to obtain and maintain required state licensing and carrier appointments.
• PC experience with operating systems.

• Competitive compensation: $68,100‑$102,100 annually in Wisconsin and Texas; $74,910‑$112,310 annually in Colorado (based on experience).
• Hybrid work model with work‑from‑home options Monday and Friday, office Tuesdays‑Thursday.
• Equipment for home office provided at start.
• Meal subsidy for office‑based associates.
• 401(k) plan with dollar‑for‑dollar match on first 8% and immediate vesting.
• Tuition reimbursement and access to Sentry University.
• Generous paid‑time‑off and volunteer‑time‑off.
• Group medical, dental, vision, life insurance, parental leave.
• Health and wellness benefits and employee assistance programs.
• Foundations gift‑matching program.

Sentry Mutual Insurance has been protecting businesses and individuals since 1904. With headquarters in Stevens Point, Wisconsin, we are one of the largest and financially strongest mutual insurance companies in the United States.

Sentry is an Equal Opportunity Employer. We do not discriminate on the basis of race, color, national origin, religion, sex, disability, age, marital status or sexual orientation. We are committed to a diverse and inclusive workplace.