Business Details
42 Years
experience
Your Trusted Insurance & Risk Management Partner in Gary, IN
Haywood & Fleming Associates has been a trusted independent insurance agency since 1984, serving commercial clients across Northwest Indiana, Chicago, and surrounding suburbs. Our expertise lies in delivering tailored risk management solutions and employee benefits programs for complex organizations. Through strategic partnerships with clients and insurers, we prioritize personalized service, cost-effective strategies, and proactive advocacy. Our team combines decades of industry experience with a commitment to navigating evolving insurance landscapes, including healthcare reform compliance.We specialize in property/casualty coverage, group benefits administration, and comprehensive risk assessments that align with organizational objectives. Our approach emphasizes transparency, client education, and leveraging industry relationships to secure competitive rates and value-added services. With a legacy built on integrity and results-driven solutions, we remain dedicated to protecting our clients' interests through customized insurance programs.
Services
Risk Assessment
Employee Benefits
Risk Management
Property Insurance
Casualty Coverage
Group Benefits Review
Self Insurance Solutions
COBRA Administration
Healthcare Reform Compliance
Loss Control Services
Details
- Year established: 1984
Highlights and features
- We offer 40+ years of commercial insurance expertise since 1984
- Our team provides personalized risk management strategies for complex organizations
- We negotiate competitive rates through relationships with top-tier carriers
- We specialize in healthcare reform compliance and employee benefits administration
- Our local market knowledge serves Northwest Indiana and Chicago businesses
Services
Employee Benefits
We design and administer comprehensive employee benefits packages including health, dental, life, and disability insurance. Our services cover carrier negotiations, compliance management, and employee education programs. We help organizations optimize benefits while controlling costs through strategic risk assessment and market analysis.
Risk Management
Our risk management services identify organizational exposures and develop mitigation strategies. We conduct detailed risk assessments, implement insurance programs, and provide ongoing monitoring. Our approach combines industry expertise with customized solutions for commercial clients across multiple sectors.
Property & Casualty Insurance
We offer tailored property and casualty insurance solutions for businesses, including directors and officers liability, general liability, and workers' compensation. Our services encompass policy review, claims advocacy, and risk control strategies to protect commercial operations.
Group Benefits Review
Our group benefits review evaluates existing health, life, and disability programs to ensure optimal coverage and cost efficiency. We provide carrier comparisons, utilization analysis, and recommendations for improving benefit structures and employee satisfaction.
Self Insurance Solutions
We develop self-insurance programs with stop-loss coverage and high-risk retention strategies. Our services include financial risk assessment, claims management, and regulatory compliance support for organizations seeking alternative insurance structures.
People
Roosevelt Haywood III
Agency Principal/Team Leader
Second-generation insurance professional with 40+ years experience. Established Haywood & Fleming Associates in 1984. Specializes in commercial risk management and strategic insurance solutions for complex organizations.
Leslie Skinner-Leslie
Vice President of Marketing & Operations
Commercial lines expert with extensive marketing and operations management experience. Oversees client relations and service delivery for major accounts. Focuses on innovative insurance solutions and client education programs.
Roosevelt Haywood IV
Agency Service Representative
Provides specialized insurance services and client support. Assists with policy administration, claims processing, and risk assessment documentation. Maintains client communication and service coordination.
Teena Arrington
Executive Assistant
Administrative support specialist with expertise in office operations. Coordinates internal processes, client communications, and documentation management for the agency's insurance services.
Questions
What insurance services do you specialize in?
We specialize in commercial property/casualty coverage, employee benefits administration, risk management consulting, and healthcare reform compliance for businesses.
How do you help with employee benefits programs?
We provide group benefits reviews, carrier negotiations, COBRA administration, wellness program development, and compliance guidance for health, dental, and retirement plans.
What risk management approach do you use?
Our approach includes risk identification, severity assessment, customized insurance solutions, and ongoing program evaluation to minimize organizational exposures.
Do you serve businesses outside Indiana?
Yes, we serve clients in Chicago and surrounding suburbs in addition to our Northwest Indiana service area.
