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Business Details
50 Years
experience
Your Trusted Insurance Partner in Shenandoah, IA
Wilson Insurance has served Shenandoah, Iowa since 1976, providing comprehensive insurance solutions rooted in personalized service. Founded by Bob Wilson through the acquisition of Wally Chesshire Agency, we expanded our reach by integrating Essex Insurance, Blackmon Insurance, and Teget Insurance while maintaining our core value of treating customers like family. Licensed across seven statesIowa, Missouri, Nebraska, South Dakota, Colorado, Arkansas, and Arizonawe offer commercial, home and auto, crop and farm, life and health insurance through partnerships with over a dozen carriers.

Our team of six professionals, including four licensed agents, combines decades of local expertise with industry-specific knowledge to deliver tailored coverage. As an independent agency, we prioritize customer needs by comparing multiple options to ensure optimal protection and affordability. Our commitment to community involvement and transparent communication has made us a trusted advisor for individuals and businesses alike.
Services
Home Insurance Auto Insurance Business Insurance Farm Insurance Life Insurance Health Insurance Crop Insurance Bonding Services Flood Insurance Renters Insurance
Details
  • Year established: 1976
Highlights and features
  • We offer access to over a dozen insurance carriers to find the best coverage
  • Our team has decades of combined experience in the insurance industry
  • We provide personalized insurance solutions tailored to individual needs
  • We are licensed in seven states to serve diverse insurance needs
  • We combine local knowledge with industry-specific expertise for better service
Services
Home Insurance
Our home insurance policies protect your property against damage from common perils while providing liability coverage. We offer customizable options for different home types including standard dwellings, mobile homes, and specialty properties. Our agents help clients understand policy details and select appropriate coverage limits based on individual needs.
Crop Insurance
Specialized crop insurance solutions protect farmers against yield losses and revenue declines caused by natural disasters or market fluctuations. Our experienced agents provide coverage options for various crops and farming operations across multiple states. We work closely with agricultural clients to develop risk management strategies tailored to their specific needs.
Business Insurance
Comprehensive business insurance packages protect commercial operations from potential risks including property damage, liability claims, and business interruption. We offer customizable policies for different industries and company sizes. Our agents help businesses identify potential risks and implement appropriate coverage solutions to ensure operational continuity.
Life Insurance
Life insurance policies provide financial protection for your loved ones in the event of your passing. We offer various policy types including term life and permanent life insurance options. Our agents work with clients to determine appropriate coverage amounts based on individual financial obligations and long-term planning goals.
Flood Insurance
Flood insurance coverage protects property owners against water damage from flooding events not typically covered by standard insurance policies. We provide policies through the National Flood Insurance Program and private carriers. Our agents help clients assess flood risk and select appropriate coverage for their specific property location.
People
Stephanie Osborn
Accounting/Owner
Stephanie manages accounting operations and joined full-time in 2013 after nursing career. Active in local chamber and community committees, she brings financial expertise and community commitment to the agency while balancing family time and outdoor activities.
Kathy Lightfoot
Agent, Crop Specialist
Kathy has specialized in crop insurance since 1981, building long-term relationships with farming clients. With commercial and personal lines licenses, she combines agricultural expertise with comprehensive insurance knowledge to serve clients across multiple states.
Luke Ditmars
Agent
Luke specializes in home, auto, and commercial insurance while managing agency social media. A Shenandoah native, he combines local knowledge with insurance expertise to serve clients' personal and business protection needs.
Curtis Osborn
Agent/Owner
Curtis brings diverse insurance experience including adjusting, inspection, and farming. Licensed in multiple insurance lines, he serves as sports official and community member while providing comprehensive insurance solutions to clients.
Ali McDonald
Agent
Ali represents the third generation of family involvement in the agency. Handling payroll and accounting with her mother, she combines generational knowledge with modern insurance practices to serve clients while maintaining family and antique-hunting interests.
Questions
What types of insurance do you offer?
We offer home, auto, business, farm, crop, life, health, bonding, flood, renters, and specialty insurance policies through multiple carrier partnerships.
Do you serve areas outside Iowa?
Yes, we're licensed in seven states including Missouri, Nebraska, South Dakota, Colorado, Arkansas, and Arizona while maintaining local Shenandoah roots.
How do you help find affordable rates?
As an independent agency, we compare coverage options from over a dozen insurance carriers to find competitive rates that meet your specific needs.
Can I make insurance payments online?
Yes, we offer convenient online payment options through our website for policyholders needing to manage their insurance accounts electronically.
What sets you apart from other agencies?
We combine decades of local experience with multi-state licensing and personalized service, maintaining family-owned values while offering access to multiple insurance markets.