Cycle Dealership Sales Specialist

001 Sentry Insurance Company; Town of Texas (WI); Hybrid; USD 68,000 - 102,000; Full time

Benefits offered by this job

Hybrid work flexibility

Tuition reimbursement

Comprehensive benefits package

401(k) with company match

Job summary

Sentry Insurance Company is seeking a Cycle Dealership Sales Specialist to grow profitable premium via dealer engagement in a defined Central US territory. You will coordinate training, manage relationships, handle complaints, and drive leads within your territory.

The role requires 3+ years in insurance, associate degree, willingness to travel up to 50%, and a valid driver's license. P&C license is preferred. We offer hybrid work options, strong benefits, and a path for professional growth.

Qualifications

• Associate degree or equivalent work experience required; bachelor’s degree preferred.
• 3+ years of related insurance industry experience.
• Familiarity with motorcycle dealership operations.
• Effective human relations and communication skills; sales experience.
• Ability to travel up to 50% within territory; valid driver’s license; P&C license preferred.

Responsibilities

• Coordinate and lead motorcycle dealership training and relationship management.
• Promote product at motorcycle events to build production sources.
• Provide product and claims expertise to dealerships to increase production.
• Develop partnerships with dealership Finance & Insurance and service departments.
• Develop new lead sources to hit sales and premium objectives.
• Identify and execute branding opportunities at the dealership level.
• Provide product management recommendations based on dealer feedback.

Skills

Relationship management

Sales experience

Communication skills

Travel 50%

Education

Associate degree or equivalent

Bachelor's degree preferred

Tools

PC experience

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%) 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.

Here is what you can look forward to as part of our team:

At Sentry, your total rewards go beyond competitive compensation. We’re committed to supporting the whole you, which is why we offer a comprehensive package designed to help you thrive both professionally and personally.

• Hybrid Flexibility: Enjoy the best of both worlds. With optional work from home on Mondays and Fridays and join your team in the office Tuesday through Thursday to collaborate and learn. We provide the technology and tools you need for both your office and home workspace from day one.
• Dining on Us: Depending on your location, we may provide a stipend that can be used at our on-site cafeteria or a meal allowance to keep you fueled.
• Continuous Learning: Unlock your potential through Sentry University and take advantage of our tuition reimbursement program.
• Comprehensive Benefits: We support your whole self with group medical, dental, and vision insurance along with parental leave, pet insurance, caregiver leave, and wellness resources. Options for HSA, FSA, and Dependent Care FSA are available.
• Work-Life Balance: Enjoy your generous Paid Time Off allowance to rest and take advantage of paid Volunteer Time Off to support your community.
• Investing in Your Future: We’re committed to your long-term financial well-being. We offer a 100% company match on the first 8% you contribute to your 401(k) each pay period, and those funds vest immediately.
• Giving Back: Through the Sentry Foundation, we’re proud to support the United Way and make a difference in our communities.

Why Join Sentry?

At Sentry, we believe our people are the heart of our success. We’re proud to be recognized for the culture we’ve built, earning spots on Forbes’ lists for America’s Best Midsize Employers and Best Employers for New Grads, as well as Newsweek’s America’s Greatest Workplaces for Women and Diversity. These honors reflect our commitment to your professional satisfaction and growth.

Building on a Legacy

Our future is bright, but it’s anchored in a long history of stability. Since our founding in 1904, we’ve dedicated ourselves to helping businesses protect their futures. That trust has made us one of the largest and most financially stable mutual insurance companies in the U.S. We’re proud to have maintained an A+ rating from A.M. Best, the industry’s leading authority, for over 30 years.

Your Career, Our Community

Whether you’re working at our headquarters in Stevens Point, Wisconsin, or one of our many offices across the country, you’ll find a challenging and rewarding environment. Explore the Our Teams tab on our Career Page to see the diverse career paths we offer, with a focus on ongoing development and professional growth.

Ready to own your future? Join us at Sentry, opportunities await!

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.

Our associates are the most important part of our company. We became one of the most financially strong mutual insurance companies in the U.S. by striving to provide the best possible service to our business customers. We do this by having conversations, forming relationships, and getting to know the people we work with and their businesses. We make that same commitment to our associates. When you join Sentry, we don’t just want you to perform tasks each day. We want you to enjoy your time with us. You’re in the driver’s seat of your career path here—sharing feedback, creating goals, accessing professional development resources, and identifying how you can contribute to both your success and the success of the company. Yes, we work hard. But we work with the purpose of helping others, and with the understanding that there’s more to life than work. We invite you to learn more about us. You’ll find we’re much more than insurance.