Business Details
42 Years
experience
Trusted Insurance & Risk Management Services in Gary, Indiana
Haywood & Fleming Associates has been a trusted independent insurance agency since 1984, specializing in tailored insurance and risk management solutions for commercial clients. Founded by Roosevelt Haywood III, a second-generation insurance professional, we combine decades of industry expertise with personalized service to meet the complex needs of public and private sector clients across Northwest Indiana, Chicago, and surrounding suburbs. Our approach centers on building strategic partnerships with clients, industry professionals, and underwriters to deliver efficient, effective outcomes. We offer comprehensive services including risk assessment, employee benefits administration, and commercial insurance coverage negotiation. Our team provides hands-on support for healthcare reform compliance, claims analysis, and customized benefit plan design.With a focus on proactive risk management, we help clients identify exposures and implement insurance programs that align with their organizational goals. Our commitment to client education ensures businesses understand their coverage options and cost-saving opportunities. We leverage our industry relationships to secure competitive rates and additional value-added services for our clients. Our local presence allows us to maintain direct communication with insurance carriers on behalf of our clients. Through continuous policy review and market analysis, we ensure our clients maintain optimal coverage as their needs evolve.
Services
Risk Assessment
Employee Benefits
Risk Management
Commercial Insurance
Consulting Services
Details
- Year established: 1984
Highlights and features
- We have over 35 years of experience in commercial insurance and risk management.
- Our team maintains direct relationships with major insurance carriers for better client representation.
- We provide localized expertise for businesses in Northwest Indiana and Chicago.
- Our comprehensive approach covers risk assessment through policy implementation.
- We offer hands-on support for healthcare reform compliance and benefit administration.
Services
Risk Assessment
Our risk assessment service identifies potential threats to your organization through comprehensive exposure analysis. We evaluate probability and potential impact of risks while developing mitigation strategies tailored to your business objectives. Our team provides actionable recommendations to help protect your assets and operations.
Employee Benefits
We offer complete employee benefits administration including health insurance, retirement plans, and disability coverage. Our services include carrier research, competitive rate negotiation, and compliance support for evolving healthcare regulations. We help optimize benefit programs while controlling costs for employers.
Commercial Insurance
We provide comprehensive commercial insurance solutions including property, liability, and workers' compensation coverage. Our team assists with policy review, claims management, and risk transfer strategies. We help businesses secure appropriate protection against operational exposures.
Risk Management
Our risk management service develops customized programs to minimize organizational exposures. We implement loss control measures, safety protocols, and insurance placement strategies. Our approach combines proactive planning with ongoing program evaluation to maintain effective risk protection.
Consulting Services
We offer expert consultation on insurance program design and implementation. Our services include market analysis, policy evaluation, and claims process optimization. We work as your advocate in negotiations with carriers to ensure comprehensive coverage at competitive rates.
People
Roosevelt Haywood III
Agency Principal/Team Leader
Second-generation insurance professional with over 35 years of experience. Leads overall account administration and strategic direction for the agency.
Leslie Skinner-Leslie
Vice President of Marketing & Operations
Commercial lines expert managing marketing initiatives and operational processes. Coordinates client service delivery and team resource allocation.
Roosevelt Haywood IV
Agency Service Representative
Supports client service operations with policy administration and insurance program implementation. Provides technical assistance to commercial clients.
Teena Arrington
Executive Assistant
Manages administrative support functions and coordinates internal operations. Serves as key contact for day-to-day client communication.
Questions
What types of insurance do you specialize in?
We specialize in commercial insurance including property, liability, workers' compensation, and executive risk management solutions for businesses.
Do you work with both public and private sector clients?
Yes, we serve both public sector organizations and private businesses across Northwest Indiana and the Chicago metropolitan area.
How do you help control insurance costs?
We conduct competitive market analysis, negotiate rates with carriers, and implement cost-saving strategies through risk management programs.
What employee benefit services do you offer?
We provide complete benefits administration including health insurance, retirement plans, disability coverage, and compliance support services.
How do you support risk management efforts?
We identify business exposures, develop mitigation strategies, and implement insurance programs tailored to organizational risk management goals.
What areas do you serve?
We primarily serve Northwest Indiana, Chicago, and surrounding suburbs from our Gary, Indiana office location.
