Risk Manager

Career Opportunities with Holler Classic Corporate Office

Current job opportunities are posted here as they become available.

Holler-Classic Family of Dealerships, an Automotive News Top 150 dealership group with 12 dealerships serving the Central Florida market, has been proudly family-owned since 1938. Our Buy Smart – Be Happy brand promises include Our Best Price First, Pure and Simple and Commission-Free Sales. The perfect candidate will be based in our Group’s home office in Winter Park (conveniently located off Lee Rd.

exit on I-4). Prior dealership experience is required.

As the Risk Manager
, you will have the opportunity to make a positive impact on our business and the lives of team members and customers every day. We are looking for a driven, dedicated individual who is excited by the opportunity to join a successful team and continues to drive home the culture of success that has been built over nearly nine decades.

To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. Reasonable Accommodations may be made to enable qualified individuals with disabilities to perform the essential functions.

Duties and Responsibilities include, but are not limited to, the following:

• Serve as primary claims contact for internal stakeholders, insurance consultant, and insurance carriers throughout the claim lifecycle, from First Notice of Loss (FNOL) through closure.
• Manage and support claims across the following lines of business:
  • Workers’ Compensation:
    Injury reporting, compensability review, medical management coordination, return-to-work strategy support, and claim outcome monitoring.
  • Automobile Liability (BI & PD):
    Coverage review, liability investigations, settlement strategy coordination, and physical damage resolution.
  • Property:
    First-party property claims support including documentation, valuation coordination, and policy compliance oversight.
  • General Liability:
    Third-party bodily injury and property damage claims advocacy, including negotiation support and mediation participation.
• Review policy language, coverage triggers, limits, and exclusions; provide insureds and production teams with informed coverage guidance.
• Participate in claim reviews, loss runs analysis, and meetings with carriers.
• Maintain detailed claim documentation and ensure timely communication of claim status and outcomes.
• Collaborate with Senior Management to coordinate safety inspections of dealerships and other company facilities.
• Chair Risk Performance / Safety Committee; convening members representative of company to review potential risks, strategize risk mitigants, and make recommendations to Executive Management.
• Other duties as assigned.

• 5+ years of experience in Property & Casualty claims handling or claims advocacy (carrier, TPA, or agency).
• Working knowledge of Workers’ Compensation, Auto Liability, Property, and General Liability claims.
• Strong understanding of carrier claims processes, coverage analysis, and loss control principles.
• Florida insurance license preferred.
• Ability to work weekdays and weekends as needed.
• Reliable transportation.
• Valid driver’s license with acceptable driving record.
• Acceptable background and drug screening.

• None

• Full-Time
• 401(k) & 401(k) Matching
• Employee Assistance Program
• Health Insurance
• Vision Insurance
• Life Insurance
• Flexible Spending Account
• Paid Time Off After 6 months
• Referral Program
• Associate Discount Program

• Ability to work a flexible schedule.

• $80,000 - $100,000 annually

Holler and Classic Family Collection of Dealerships is proud to be an equal opportunity workplace. We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, Veteran status or other legally protected characteristics. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. We participate in the E-Verify program.

Upon an applicant's request, Holler and Classic Family Collection of Dealerships will consider reasonable accommodation to complete the application process.

To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. Reasonable Accommodations may be made to enable qualified individuals with disabilities to perform the essential functions.