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40 Years
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Your Trusted Insurance Partner in Redlands, CA
Gillespie Insurance Services, established in 1986, is a family-owned insurance agency and brokerage based in Redlands, CA. Specializing in tailored insurance solutions for specific industries, we began with agricultural insurance and have expanded to serve diverse sectors including wineries, contractors, and small businesses. Our independent agency model allows us to partner with multiple top-rated carriers, ensuring clients receive optimal coverage and competitive rates. With over 35 years of experience, we combine deep industry knowledge with personalized service to meet the evolving needs of our clients.

Our team of dedicated professionals prioritizes clear communication, proactive risk management, and unwavering support, maintaining a client-first approach that has earned us long-term trust and loyalty. We are committed to staying at the forefront of industry trends while preserving the values of integrity and community that define our business.
Services
PEO Insurance Workers Compensation EPLI Flood Insurance Earthquake Insurance Supplemental Health Personal Insurance Contractor Insurance Winery Insurance Agricultural Insurance
Details
  • Year established: 1986
Highlights and features
  • 20+ years of experience in specialized insurance services
  • 24/7 support for claims and policy assistance
  • Personalized service from family-owned agency
  • Access to multiple top-rated insurance carriers
  • Expert guidance in agricultural and niche industry insurance
What people say
Best service experience Prompt claim resolution Expert industry knowledge Personalized attention Long-term trust
Services
Workers Compensation
Workers' compensation insurance provides essential protection for businesses by covering medical expenses, lost wages, and rehabilitation costs for job-related injuries or illnesses. This mandatory coverage shields employers from financial liability while ensuring employee care. Our solutions include audit support, experience modification management, and tailored payment plans for businesses with fluctuating payrolls.
EPLI
Employment Practices Liability Insurance (EPLI) safeguards businesses against claims of discrimination, harassment, wrongful termination, and other employment-related legal actions. This coverage is critical for California employers facing strict labor laws, providing financial protection for legal defense costs, settlements, and regulatory penalties while supporting workplace compliance and risk management strategies.
Flood Insurance
Flood insurance covers property damage from external water sources like heavy rains, overflowing rivers, and storm surgesperils excluded from standard policies. We offer both private flood insurance and NFIP options for residential and commercial properties in high-risk areas, ensuring comprehensive protection for structures and contents against devastating water damage events.
Supplemental Health Insurance
Supplemental Health Insurance provides lump-sum payments for specific medical events like accidents, cancer diagnoses, or hospital stays. This non-duplicative coverage works with primary insurance to cover deductibles, co-pays, and living expenses during disability. Group and individual plans offer customizable benefits including accident, hospital indemnity, and short-term disability coverage options.
PEO Insurance
PEO insurance solutions combine workers' compensation, health benefits, and HR management services through strategic partnerships with leading Professional Employer Organizations. This integrated approach reduces administrative burdens, lowers insurance costs through group rates, and eliminates annual audits while maintaining employer control over workplace operations and employee management.
People
Eli Gillespie
Owner / General Manager
Eli Gillespie leads Gillespie Insurance Services with over 35 years of industry experience. Specializing in commercial risk management, he focuses on agricultural and contractor insurance while maintaining the family-owned agency's commitment to personalized service and community values.
Lydia Moyers
Commercial Account Manager
Lydia Moyers brings expertise in commercial insurance solutions, helping businesses navigate complex coverage needs. With a focus on client education and tailored risk management strategies, she ensures clients receive comprehensive protection aligned with their operational goals.
Paul Goetz
Commercial Producer
Paul Goetz specializes in connecting businesses with customized insurance solutions. His industry knowledge and carrier relationships enable him to secure competitive coverage options for clients across diverse sectors including construction and food services.
Questions
Why is my insurance rate increasing?
Rate changes reflect updated risk assessments, claims history, or market conditions. We'll review your policy details to explain specific factors affecting your premium.
How can I reduce my insurance costs?
Implementing safety programs, bundling policies, and maintaining claims-free history can help lower premiums. We'll analyze your situation to identify cost-saving opportunities.
Why was my claim denied?
Claims may be denied due to policy exclusions, insufficient documentation, or coverage limitations. We'll help you understand the decision and explore resolution options.
Can I temporarily pause my coverage?
Coverage modifications require underwriter approval. We'll discuss your specific needs to determine viable options while maintaining compliance with insurance regulations.
How do I obtain a certificate of insurance?
Request certificates through our online portal or contact our team directly. We process standard requests within one business day to support your contractual requirements.