Meet the Team

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John C. Osborn

I pride myself on my ability to share with independent insurance agents vital sales experience, marketing strategies, technical advice, legislative updates, stellar support, and a common sense approach to the insurance industry. Our agency provides exemplary service to exceptional agents, and we are known for building lasting, trusting, and loyal relationships. We find that our approach benefits independent agents, our clients, and the companies we represent. Our local in-house expertise, knowledge, and vision continue to allow us to maintain an extremely competitive portfolio of carriers and support to you or your agency. Working with our team lets you focus more on growing your business and serving your clients’ needs.

President  |  Licensed 08/20/2002  |  Extension #602

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Gary J. Osborn RHU LUTCF

My career began in 1972 as an agent going door-to-door selling accident plans. Twenty-three years after a successful career as a sales agent, field trainer, and branch sales manager for three different sales organizations, I decided to open an independent agency in Springfield, MO. I founded Osborn and Associates in April of 1993 and was fortunate enough to attract a core sales force of exceptional agents to help get us off the ground. Many of these agents are still our partners today.  We take pride in the relationships we build and the support we provide.

Founder |  Licensed 12/29/1972  |  Extension #603

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Tiffany A. Williams

I began my career with Osborn and Associates in December of 2008 as a receptionist. As I began to service agents, I started developing the necessary skills and insurance understanding to service clients as well as agents. In September of 2009, I became a licensed agent myself. I grew out of the receptionist position and into an agent role that specializes in Medicare. Since this market is always changing, I understand the significance of knowing the very latest compliance, rules, and regulations. I have the heart and passion to see that each client of mine and each agent I service is taken care of 100%. I love what I do and I love helping people, whether they are clients or agents.

Licensed Agent  |  Licensed 09/29/2009  |  Extension #601

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Terri J. Weaver

Throughout my career in the insurance industry, I have worn many hats. I started as a receptionist for a brokerage with in-and out-of-house agents here in Springfield, and then earned my Life & Health license in 2001. From there, I advanced to the Group Renewal Department where I was privileged to assist the agents in maintaining their employer group health. In 2011, I became a career agent with Mutual of Omaha. There I was able to spread my wings to learn about senior, life, and financial products and to get a sense of the sales perspective. Through the years, I have learned that I enjoy working with both agents and customers, and Osborn and Associates allows me that opportunity. Our agents are fantastic to work with, and I enjoy meeting and working with so many great people. I enjoy the challenge of learning new things, and I look forward to many more years of working with this fantastic team of people who have the same focus I do.

Licensed Agent  |  Licensed 03/19/2001  |  Extension #605

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Betty L. Johnson

I am a client focused and service oriented professional that has spent over 20 years in sales, contracting and customer service.  As a native of Bolivar, my early years were here in Springfield where I worked for MCI as a sales consultant and supervisor. My husband and I moved to Fort Worth, Texas and spent 10 years in the Metroplex working as a customer service representative, mortgage loan officer and Underwriter for Countrywide Home Loans and Bank of America.  My family moved back to the Springfield area to be closer to our immediate family and this path has led me to the wonderful Osborn and Associates.

Receptionist and Licensed Agent  |  Licensed 03/23/2018  |  Extension #606

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Haley N. Schroff

I am the person who will coordinate and manage all the events here at Osborn and Associates. From conferences to community and social events, I plan and facilitate each one. I studied Event and Meeting Planning at St. Louis Community College and Ashworth College, and am currently working to become a Certified Meeting Planner. I have had the chance to put my skills to work for small businesses and non-profit organizations for the past three years. I consistently work towards making each event more memorable and exciting than the last to show that Osborn and Associates is the best place for our clients and agents.

Events and Social Media | Extension #604

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Dean L. Carpenter

I am excited to be the new contract specialist at Osborn Insurance Group.  After completing my naval career I launched into real estate sales and investing, where I learned the importance of understanding contract language, compliance, documentation, and follow-up.  The impact of these on each party and agency, however, cannot be compared to that of our relationship in creating a smooth transaction.  I love getting to know agents, investors, and clients, as it makes the experience very rewarding. I am moving from Mountain Home, AR, where I worked for the local hospital with a fantastic team of professionals. I look forward to getting to know our agents and serving their contracting needs.  Please come by and let me know how I can help you in your business.



R. Boyd Field

Over the years, I have worked in various roles within the insurance industry.  I assisted a local agency with everything from submitting applications to answering the phones.  I learned to adjust claims and resolve provider issues for a major carrier.  Most recently, I worked for a local hospital managing provider contracts with multiple carrier networks.  Now, working here at Osborn Insurance Group, I am excited to return to the local agency side to manage commissions, licenses and contracts. Through it all, I have acquired an eye for the details and a mind for numbers.  However, the most important lesson I have learned is to remember the people behind the numbers. I look forward to meeting all of our agents and ensure the accuracy of all their financial transactions.

Commissions and Licensing

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Preston M. Tate

I am a web designer and developer with a passion for creating beautiful and easy to use websites. I have degrees in Computer Science and Mathematics. My goal is to use my technical expertise and eye for design to make our websites clean and organized in a way that allows our clients to find what they are looking for without having to search. I have designed and built a number of websites for churches, small businesses, and non-profits and will use my experience to constantly be looking for ways to improve our customer experience online. I will consistently work towards making Osborn Insurance Group be one of the best online experiences possible.

Website and Marketing