Cycle Dealership Sales Specialist

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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

At Sentry, your total rewards go beyond competitive compensation. Below are some benefits and perks that 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

We take great pride in making Forbes’ list of America’s Best Midsize Employers. A lot of different factors go into that honor, many of which contribute to your job satisfaction.

Our bright future is built on a long track record of success. We got our start in 1904 and have been helping businesses succeed and protect their futures ever since. Because of the trust placed in us, we’re one of the largest and financially strongest mutual insurance companies in the United States. We’re rated A+ by A.M. Best, the industry's leading rating authority.

Our headquarters is in Stevens Point, Wisconsin, with offices located throughout the United States. From sales to claims, and information technology to marketing, we enjoy a rewarding and challenging work environment with opportunities for ongoing professional development and growth.

Get ready to own your future at Sentry. Opportunities await!

Casey Van Der Geest

Talent Acquisition Specialist

Casey.VanDerGeest@sentry.com

Equal Employment Opportunity

Sentry is an Equal Opportunity Employer. It is our policy that there be no discrimination in employment based on race, color, national origin, religion, sex, disability, age, marital status, or sexual orientation.

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5 Questions You Should Ask During the Interview

Here are 5 questions we think you could ask during your interview. Use them as a guide to help you write your own questions.

Remember: Always have at least 5 questions prepared for the interview. If you do not, you run the risk of looking unprepared.

What does success look like in this role, and how is it measured?

Why ask this? You want to ensure you have a clear understanding of expectations before accepting the role. Knowing how success is measured helps you hit the ground running and avoid surprises about performance evaluations. It also signals to the employer that you're results-driven.

Can you describe the team dynamic and the company culture?

Why ask this? Skills and experience matter, but if the work environment isn’t a good fit, you won’t be happy or productive. This question helps you gauge whether the company values collaboration, how teams interact, and whether the culture aligns with your work style and values.

What are the biggest challenges facing the person in this role right now?

Why ask this? Every job has challenges, and it’s better to know them upfront. This helps you assess whether the role is a good fit for your strengths and whether the company is realistic about its expectations. If they hesitate to answer, it could be a red flag.

How does the company support work-life balance and employee well-being??

Why ask this? Burnout is real, and some companies expect employees to sacrifice personal time for the job. By asking this, you’ll get a sense of how they value work-life balance, flexibility, and well-being—things that are crucial for job satisfaction and long-term success.

These questions help you make an informed decision while also showing your professionalism and strategic thinking!

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