By Patricia A. Scheyer
NKyTribune reporter
Fort Wright CAO Jill Cain Bailey has decided to call it quits and retire from the career she has built for the last 31 years.
“I realize that I am younger than the average retiree, young enough to have another career,” she said, laughing. “But the pension system kind of dictates the time to retire. I’ve been in the pension system for 31 years, and I just reached a point where it was time to exit the system. You reach a point in the system where your pension doesn’t earn any more money and while I’m not criticizing the pension system, I decided it is the right time to retire.”

A pioneer in her field, Jill is very proud that up until she became a Chief Administrative Officer at Taylor Mill at the tender age of 24, there were very few women in the profession in Kentucky.
“I have very much enjoyed seeing the change in CAO opportunities,” she recalled. “I am thrilled to have started my career at such a young age. There are so many men who are true professionals, some who have mentored me. I was told I could only do the job until I had kids, which was a common thought back then, one I didn’t take seriously, but I had to battle through that mentality. I can’t take credit, but I did feel that I led a small charge for women in the Commonwealth.”
Jill didn’t plan a career in city administration; she thought she would be a lawyer. Born and raised in the Erlanger/Elsmere area, she attended Lloyd High School and then went to NKU where she took classes in political science and speech communication and other classes suited to pre-law. She worked for Senator Wendell Ford and for Kenton County Fiscal Court Judge Executive Clyde Middleton. But when the job came open at Taylor Mill for a Chief Administrative officer, she liked the job and changed her mind about becoming a lawyer, staying at the city for 23 years.
“My mother was a council member in Erlanger for a few years, and that gave me a good understanding of city work,” she said. “My dad was a postal worker, my mom a social worker, and my sister was a teacher, and a principal. The thought I was brought up with was that you get a job and you keep it till you retire.”
There was a time at Taylor Mill when people were making life unpleasant, and Jill realized she would have to change jobs, even though she loved Taylor Mill and the people she worked with. At the time, Fort Wright was looking for a new CAO, but the deadline to apply had just passed, so she called Mayor Dave Hatter, and he told her it wasn’t too late and encouraged her to apply. Turns out, she was a perfect fit for the job, and even now she says she hates to leave.
“It is bittersweet,” she explained. “I am very sad to leave. But life is like that. I feel that I have had to re-invent myself a few times. I had to leave Taylor Mill and find another job, I had a divorce, and I had to figure out how to raise two kids as a single mom, and I had a major illness and had to figure out how to go on after surviving that.”
Jill found out that she was sick shortly after taking the job at Ft Wright. The doctors told her that her markers for cancer were high, so she had a partial hysterectomy, and felt better, but her markers didn’t improve.
“My sister had a mammogram and they found out she had stage one breast cancer, so I thought I should at least have a mammogram, although I had already had an MRI, and nothing showed up,” she remembered. “I hadn’t even gotten back to my office when they called me and told me to come back in. I hadn’t been good about regular checkups like mammograms, and I highly recommend that for anyone. They thought it was stage one non-hereditary cancer, like my sister’s, but after I had surgery, they changed that and said it was stage three. I had surgery at Christ Hospital and chemo and radiation at UC, the Barrett Center. I really like my medical care team – I can’t say enough good things about them.”
As hard as it was to go through surgery and cancer treatment, Jill said the city rallied around her and helped her through it.

“Everyone was so great, and really helped me, every single person on council and in the city stepped up to help me,” she said. “And I credit my sister with helping me through it too, she sat with me through every chemo appointment. But I have to say, having cancer changed the way I view life. I really appreciate life and people more now. It forces you to face the fact that life could end, right now. It is a bleak reality. But it also makes you want to enjoy every minute of what life you have.”
Jill has had some honors and responsibilities in her jobs.
She received the City Administrator of the Year in 2002, early careerist category, by the Greater Cincinnati Chapter of the American Society for Public Administration, and again in 2008, and in 2015, presented by the Northern Kentucky City/County Management Association. She also received the 2011 Outstanding Women of the Year Award.
Jill is the past president of the Kentucky City/County Management Association and the past president of the Northern Kentucky City/County Management Association.
Jill’s last day will be August 31, and the mayor is carefully wording the advertisement for her replacement. She said Fire Chief Steve Schewe will be filling in until the city can put a new CAO in place.
But Jill won’t let the grass grow under her feet.
Since she has been in remission, Jill has tasked herself with doing 54 new things a year that are out of her comfort zone, and it has encouraged her to try new things.
“I have had some great adventures,” she said. “This year, as a retirement gift to myself, I am flying out to Santa Monica and Los Angeles, and then driving back along Route 66. It is the 100th anniversary of Route 66. I am going with a friend, and it is a 2500-mile trip, through 8 states. We will end up in Chicago. I am also going to spend a week in Florida. We have some fun things planned, and we are going to hit some high notes.”
Her children, Trenton, 23, and Addison, 21, keep her busy too.
“Addison and I have started a home bakery, called Dipped Delights Bakery, LLC,” Jill announced. “We did it together. She makes the best banana bread, and I wanted to try to make cake-sicles. I have always liked baking.”
Addison will graduate next year with a bachelors in nursing, and Trenton, a police officer in Taylor Mill, as well as owner of a lawn care business called Total Turf, is engaged and due to be married next year, so life with the children is lively.

Looking back at her career, she remembered that she worked on the project of widening Pride Parkway, and working on economic development. In Fort Wright, she has loved working on the Wyler project along the highway. She is happy that she was part of helping council to lower taxes and helping get the city into higher interest investments, which has made money for the city.
“And of course there have been bumps in the road, which I look at as the learning curve of life,” she explained. “The thing I really love is that I have been able to make a difference to everyday citizens’ lives. That is a hallmark of the job. As I look back, I have no regrets. Life is too short not to be happy.”
Mayor Hatter has been in city government for 28 years, 16 as a council member and almost 12 as mayor, and he says unequivocally that Jill is the best city administrator they have had.
“I am happy for her and sad for us,” he said. “She has so much knowledge, and experience, but most of all she has been a trusted partner. I have so much stuff going on in my life, and I trust her to do everything. I understand, and she understands. There is no way I would have lasted this long without Jill. I don’t micro-manage things at the city. She has always kept things going so that I can do the stuff I need to do. She is a friend, and a great partner. I am so sorry to see her go, but I wish her the very best.”
It has been mutual, and Jill said Hatter has been amazing to work with, calling him a great leader and a great thinker, serving for all the right reasons.
Jill looks back at the working relationships and all the positive changes and knows that although she hates to leave Fort Wright, she understands that the next CAO will be someone who fits well with council members and the city. She said a CAO has to be able to multi-task, and they should be empathetic, qualities that women tend to have, to add to the qualifications that candidates show on their resumes.
“I am happy to be part of Fort Wright’s legacy,” Jill said. “Cancer may limit my days on earth, I will never say that I beat it. It could come back. But I believe in being happy and positive, and though I have always lived my life authentically, I want to appreciate life even more. I have had an amazing career, great kids and a great life. I feel blessed!”




