001 Sentry Insurance Company · Madison, WI

Cycle Dealership Sales Specialist at 001 Sentry Insurance Company — Madison, WI

Full-timeMadison, WIPosted 2026-07-14Apply on Workday

Full job description

As a Cycle Dealership Sales Specialist, you will contribute to profitable premium growth by increasing motorcycle dealer engagement with our motorcycle insurance product.

Sentry’s motorcycle team is seeking a motivated, self-starter who has a passion for building and maintaining strong relationships with motorcycle dealers within a defined territory. This position will manage a large geographic territory and will be staffed within the Central US territory.

What You'll Do

As a Cycle Dealership Sales Specialist, you will coordinate and lead motorcycle dealership training, relationship management, complaint handling, prospecting and communication within your territory.

Additionally, you will:

  • Promote product and brand at assigned, motorcycle events to identify and foster production sources and relationships.
  • Provide insurance product expertise and leads product and related process training efforts for dealerships and related affinity associations.
  • Provide comprehensive motorcycle product and claims expertise to dealerships to increase production.
  • Develop and maintain strong partnerships and rapport with motorcycle dealership Finance & Insurance departments as well as Service departments in order to foster strong service levels and profitable business.
  • Promote product and brand at assigned motorcycle events to identify and develop additional production sources and relationships.
  • Develop new, and enhance existing dealership quote/lead sources to achieve sales and premium objectives
  • Identify, create and execute branding opportunities at the dealership level.
  • Implement plans and programs to contribute to the achievement of dealer produced sales and premium objectives.
  • Provide product management recommendations on specific product change using industry and product knowledge along with feedback from dealerships and affinity partners.

What it Takes

  • Associate Degree or equivalent work experience required, Bachelor’s degree preferred
  • 3+ years of related work experience in the insurance industry, with familiarity of Motorcycle dealership operations and departments
  • Basic knowledge of or experience with motorcycles is preferred
  • Effective human relations and communication skills to communicate with dealers and potential/existing customers
  • Sales experience and knowledge of professional sales techniques, including presentation skills preferred.
  • Ability to meet travel requirements of the job (50%-75%) within assigned territory.
  • Acceptable Motor Vehicle Record and valid driver's license.
  • P&C Insurance license preferred. If no license, you must have the ability to obtain and maintain required state licensing and carrier appointments.
  • PC experience with knowledge of various operating systems.

Based on experience and qualifications, the pay range for this position is:

  • For candidates located in Wisconsin and Texas: $68,100-$102,100 annually.
  • For candidates located in Colorado: $74,910-$112,310 annually.

What You'll Receive

  • Sentry is happy to offer flexibility through a scheduled Hybrid work model. Monday and Friday work from home if you choose to, Tuesday through Thursday you’ll work in office.
  • As a Sentry associate, you will have an in-office workspace and materials for your home office. In addition to the laptop, you will receive prior to your start, Sentry will provide equipment for your home office.
  • Meal Subsidy available for associates who report to an office.
  • 401(K) plan with a dollar-for-dollar match on your first eight percent, plus immediate vesting to help strengthen your financial future.
  • Continue your education and career development through Sentry University (SentryU) and utilize our Tuition Reimbursement program
  • Generous Paid-Time Off plan for you to enjoy time out of the office as well as Volunteer-Time off
  • Group Medical, Dental, Vision, Life insurance, Parental leave, and our Health and Wellness benefits to encourage a healthy lifestyle.
  • Well-being and Employee Assistance programs
  • Sentry Foundation gift matching program to encourage charitable giving.

About Sentry

Casey Van Der Geest

Talent Acquisition Specialist

Casey.VanDerGeest@sentry.com

Equal Employment Opportunity