Waterloo is home to the longest-tenured agent in all of State Farm history, as Roy J. May extended his record service this year when he celebrated 75 years of working with the insurance company.

May said he has enjoyed his career, noting that, as an agent, he is an independent contractor.

“As a business owner, you get to make all the decisions in your office — who you hire, how you handle your business, et cetera,” he said. “So no one can tell you what to do, but to succeed you need to be self-motivated, organized and professional. If you succeed or fail, it’s up to you. There is no safety net.”   

May added that he picked a great company to work for when he started his career and has worked every day since to “represent the company, contribute to (my) community and to insure and protect the many generations” that he has worked with over the years. 

May’s life’s work began when George J. Mecherle, founder of State Farm, had a hand in hiring him in 1945. 

May had recently returned from serving in the Army Air Corps in Texas during World War II that February when the local State Farm manager, E.A. “Mac” McLaughlin, came to Waterloo to speak to May’s father about becoming a state farm agent. 

May’s father had other ideas, looking at this 19-year-old veteran and saying “I think this is something you should do.” 

So, McLaughlin hired May, who started work on April 1, 1945. On his first day, he sold three automobile insurance policies: one for himself, one for the county sheriff at the time and one for a person whose great-grandchild now has insurance through May.

At first, May only worked one day a week and used his car as his office. 

When he got married to his wife of almost 73 years, Norma, she followed tradition and began working side-by-side with May out of their home office. 

“Mac and his wife ran a tight ship with their agency,” May said of those early years. “One life policy had to be written every week, and Mac would show up at unexpected times just to make sure you weren’t goofing off.” 

But McLaughlin was not merely a taskmaster. 

“Mac was a very hands-on manager with weekly meetings and in-agency competitions, with social events sprinkled in the mix,” May said before adding he misses that camaraderie between agents. 

May said he and Norma learned how to conduct themselves, run a successful business and maintain a desire to succeed from the McLaughlins. 

Over the years, May, who has worked during 13 U.S. presidencies, has witnessed myriad changes, perhaps most notably in the technological realm. 

He has files of handwritten notes, microfilm copies of those same files and must remain updated on computer skills. 

 Even as the particulars of doing business changed, May said State Farm is not very different from the way it was in 1945. 

“The mantra of always trying to do the best for the customer and the company has always been at the forefront,” May said. 

Throughout his career, May has done just that, receiving numerous honors and awards for his work. 

His favorite reward was an organization called the Millionaire Club, which provided agents who met certain benchmarks with annual exotic travel opportunities. 

Through the club, Roy and Norma – who Roy said “was as good a manager as Mac”– went to destinations like Hawaii, Europe, Mexico and Hong Kong, meeting agents from across the country who became their friends. 

May has visited all seven continents throughout his life and said he enjoys introducing his seven children, 11 grandchildren and five great-grandchildren to the world on family trips.  

Those benefits helped counterbalance the difficult parts of May’s job, like having to cancel someone’s policy for various issues. 

“The company can hide behind the paperwork, but as the face of the company I am charged with delivering the bad news,” said May. “As you can imagine, that is never easy.” 

As busy as he has stayed with State Farm, May has also managed to give back to the community in which he has insured four generations of people. 

He was a charter member of the Waterloo Optimist Club, the parade marshal for the Waterloo Homecoming parade for over 20 years and was instrumental in the construction of the Knights of Columbus Hall in Waterloo. May also served 26 years on the Bi-State Board and still serves as Commander of American Legion Post 747. 

A devout Catholic, May is a member and financial supporter of Ss. Peter & Paul Catholic Church in Waterloo and has ties to the Old Cathedral in St. Louis. 

With a plate that full, and the State Farm record his by three years, some might think May is ready to retire. 

But he said he has “no immediate plans” to do so.