Our Team & Services

Our Team

Stephanie Osborn, Accounting/Owner

Stephanie joined the team part time in 2009 assisting her mother, Sharon, with the bookkeeping. In 2013, she retired from nursing to join the agency full time and oversees the accounting and payroll. Stephanie is on the Shenandoah Chamber and Industry Association Board and Tannenbaum Tea Committee. She enjoys spending time with family and friends and her granddaughters, working outside in the yard, taking walks, cooking and traveling.

Contact Stephanie:
stephanie@wilsoninsurancestore.com

Kathy Lightfoot, Agent, Crop Specialist

Kathy joined Wilson Insurance in 1981 and became Bob’s first agent. Over the years, Kathy became the agency’s crop specialist and has a longstanding relationship with her many farming customers. Kathy also has her commercial and personal lines licenses. Kathy enjoys spending time with her family and grandchildren.

Contact Kathy:
kathy@wilsoninsurancestore.com

Luke Ditmars, Agent

Luke joined the Wilson team in 2013 and specializes in home, auto and commercial insurance. He also oversees our social media pages. Luke was born and raised in Shenandoah. He enjoys golfing, kayaking, hunting and fishing, cooking and video gaming.

Contact Luke:
luke@wilsoninsurancestore.com

Curtis Osborn, Agent/Owner

Curtis joined Wilson Insurance in 2015. He has prior experience as an insurance adjuster, inspector and agent and also in farming. He has all of his licenses, including commercial, home and auto, life and health and crop insurance. Curtis is a high school and middle school sports official and has coached various youth sports. He is a member of the Shenandoah Elks Club and an auctioneer.

Contact Curtis:
curtis.j.osborn@gmail.com

Ali McDonald, Agent

Ali joined the agency in 2020, became a licensed agent and also does payroll and accounting with her mother. Ali is a 3rd generation family member in the Wilson Agency. She enjoys spending time with friends, family and her daughters, Bria and Lennon. Her favorite activity is finding treasures at thrift and antique stores and garage sales.

Contact Ali:
ali@wilsoninsurancestore.com

Jaylee Miller, Customer Service Rep

Jaylee joined Wilson Insurance in August, 2025 as our customer service representative. She greets customers with a warm friendly smile. Jaylee grew up in Rockport, Missouri and lives with her husband in Shenandoah.