Leading Change

Sandra Wilson has crafted a life filled with love, adventure and professional accomplishment.

After being appointed Ocala’s city manager in June, Sandra Wilson went into her spacious new City Hall office on a Saturday, alone, to hang her three framed college degrees and her certifications, put up photos of family members, and bring in a treasured orchid in full blossom.

It was a sweet moment of victory—and a chance to reflect on her journey and the sacrifices she made along the way.

In her 20 years with the city, Wilson has served as deputy city manager, assistant city manager for support services and human resources (HR) and risk management director. She is best known, she says, for her “hallmark” of fairness.

“I had to be fair, especially in HR,” she notes, “because people trust you more when they believe you are fair. They might not like your decision, but they respect you if you are fair.”

When asked to describe other personality traits, she erupts in laughter, playfully slaps her beautifully manicured hands on her desk, and declares, “I’m fun! And I’m a lover of people.”

Rise, Rise, Rise

Wilson was born in Dade City and spent her early childhood in Hernando County. When she was in seventh grade, her parents divorced and she and her older sister moved with their mother to Wildwood, where they had extended family. She says she was a “pretty good student,” but then lost interest in education.

She was keen, however, on something else.

“Ever since I was a little girl, I wanted to be like a secretary,” she says with a smile. “My mom bought me and my sister little typewriters and little desks. I always wanted to have an office.”

It was at Wildwood High School that she learned how difficult becoming a secretary might be.

“It was funny because I was like, ‘I’m never going to learn how to type. This is hard.’ But then you learn it.”

She graduated high school, then balked at going to college and joined the U.S. Navy instead.

“I left for boot camp on my 18th birthday,” she explains. “Even though you go through medical exams before you arrive, once you get there you go through additional exams. I have severe eczema and they determined that, with that skin condition, I wasn’t a good fit for military life. So, I came home and got a job at Maas Brothers in the mall in Ocala. My Mom said, ‘You have to go to college.’ I said, ‘OK, OK, OK.’”

She enrolled at Lake-Sumter Community College in Leesburg and got a job with Barnett Bank in Eustis.

“I was going to college part-time in the evenings and it took me five years to get a two-year degree because I was going part-time,” she notes with pride of her associate degree in office systems technology.

She soon took a job with the city of Eustis, as recording secretary.

“I put together all of the agenda packets, did the minutes, all of the handling of land use ordinances,” she notes. “I had to read everything. I had to go to the commission meetings, so I understood all of the decisions that were being made. You learn a lot in that position. I worked there for seven years.”

While in that job she would see interesting job openings and “look at the people around me that had higher level jobs. And I would think, ‘Oh, I could do that job,’ but I didn’t have the education,” she reflects. “I went to Saint Leo University and got my bachelor’s degree in business administration. Then I became eligible to apply for some of those other jobs.”

Before long, she became town clerk for the town of Lady Lake.

“It was basically what I was doing in Eustis, but when you work in a small town you wear a lot of hats. I was not only the town clerk, I was the purchasing officer, the personnel officer, risk management person. I told the gentleman who hired me that I knew how to do some parts really well, but there were other parts of the job I had no experience in. He said, ‘Well, it’s not rocket science, you can learn it.’ He gave me the opportunity, and I did, I learned it.”

As the job grew, the town split the duties and Wilson became the head of human resources and risk management.

And, once again, she pursued higher education.

“While I was in Lady Lake, they had a benefit where they covered the entire cost. I got my master’s degree in human resources development from Webster University,” she says. “And I did that in the evenings. I had to drive to Orlando a couple of evenings a week, but it was worth it.”

The Path Forward

Four years later, she went to work for the city of Lauderdale Lakes, as the HR director.

But South Florida wasn’t home. And she missed her mom and sister.

“Every chance I had to come home on weekends, I would do that. And on one of those trips home was when I met my husband, Jerome Wilson,” she recalls with a big smile. “That’s how God works our lives out. Because if I had still been living up here, I probably wouldn’t have been hanging out with them on the weekend…but I was. My sister had to go to the furniture store and I said to wait for me. And he was there. That was April 24th of 1999. And on August 9th of 1999 we got married. And the rest is history.”

The two have a daughter together, Kourtney, 20, who is enrolled in the law enforcement academy at the College of Central Florida, with a goal of becoming a police officer and possibly, long range, working for an agency such as the FBI.

Jerome Wilson owns a construction company in The Villages. He has a son from a prior relationship, as well as a granddaughter and grandson.

Wilson says that after she and Jerome were married, she was still living in South Florida and he was living in Bushnell when she became pregnant.

“And, just how fate would have it, I had an appointment with a gentleman with a company from out of Tallahassee and I didn’t go to work that day. I had forgotten about the appointment. I was just tired. I was newly pregnant,” she remembers. “When I went to work the following day, he called and said he was still in town and would like to talk to me. He’s the one who told me about an opportunity here in Ocala.”

Wilson interviewed with then City Manager Susan Miller on Veteran’s Day in 1999 and started with the City of Ocala on January 3rd of 2000, as head of the HR.

“Everything just lined up for me to come back to this area,” she offers. “And I was so happy to be given the opportunity and it seemed effortless. It’s been a real blessing. Even though, of course, a lot of effort went into getting prepared for the opportunity because getting your education is not easy. When my friends were sleeping in on weekends, I was on the interstate driving to school on Saturdays and Sundays. I just thank God I made it through. It took a lot of energy and sacrifice.

“I tell people, whatever you decide to do, it’s a sacrifice,” she continues. “If you decide to have your kids and that’s where you’re going to devote your energy, then you sacrifice your education and your opportunities in the workplace. If you decide to pursue your education, it’s a sacrifice of time and energy and you may put off having a family or doing something else. Anything you do, there is a sacrifice somewhere.”

She says she tells new hires with the city that if they aspire to do something more with their career, they should “determine what it takes and see what they need to do to be ready for that opportunity because when it presents itself, that’s not the time to get ready, you have to already be ready so you can apply and say this is how I’m qualified for it.”

In 2011, Wilson was named by then City Manager Matt Brower as chief of staff for support services. She also obtained certification through the International City/County Management Association. Under City Manager John Zobler, Wilson was named deputy city manager. When he retired in late 2019, she became interim city manager.

“I have professionally known Sandra prior to working with the city of Ocala, when I worked with Marion County as an assistant county administrator and interim county administrator,” notes Ocala Assistant City Manager Bill Kauffman. “I always found her to be professional and she demonstrated a desire to serve the citizens of the city. In August of 2015, I had the privilege to work for the city of Ocala as an assistant city manager, where I worked directly with Sandra in her role as deputy city manager. Again, I found her to be professional in her work and desire to make the city a better place for all the citizens. We have a great leadership team here at the city, where each of us brings a unique skill set that works together to make the city great. I am looking forward to seeing Sandra lead the city to its next level of greatness as we come out of this pandemic. The future for the city of Ocala has endless possibilities and I am sure Sandra will lead it with integrity and a steady hand to make it a great place to live, work and prosper.”   

Ken Whitehead, also an assistant city manager, has been there for five years.

“What I have appreciated most about Sandra has been her honesty and integrity as a public servant,” he offers. “She is a proven leader that I trust and respect because of her core values. I learned a long time ago that who you work for has as much to do with your job satisfaction as what you do in that job. I am delighted to work with the city largely because of the caliber of people I work with in the organization and in the community. It will be fun watching the city continue to grow and prosper in the years to come, especially with Sandra at the helm of city management.”

The Travel Bug

One of the joys of life for Wilson is traveling with family members and friends, including on couple’s getaways each Super Bowl weekend, to the mountains of Tennessee.

“We get this huge 12-bed, 12-bath cabin,” she notes. “And we’ve gotten to know each other very well and we support each other.”

She says she and Jerome really enjoy visiting New York City.

“We love going to the Broadway shows, Central Park, going to Macy’s, just walking around, going to comedy shows. We just love the city,” she says. “I don’t know if it will ever be the same. But that’s our favorite place to go. We went last year for our anniversary.”

She says they also “loved Canada. We went to Toronto when our daughter graduated.”

They had trips lined up this year for Jamaica, Charleston and Myrtle Beach, which were all cancelled because of the pandemic. A planned journey to Dubai is in jeopardy.

“And I just got inducted as president of the Rotary Club of Ocala. I was supposed to go to the Rotary International convention in Honolulu, Hawaii, but that got cancelled,” she notes with a sigh.

“I like spending time with my mom and my sister. I have other siblings, too. My dad had nine children,” she adds. “My mother only had two of those, me and my sister. We are close. She is a nurse at Ocala Regional. My mom will be 80 this year and we have a cruise planned for her 80th birthday in October, if we can go.”

Making Connections

In her precious spare time, Wilson enjoys reading and recently found a connection between Ocala and New Orleans in a book loaned to her by Ocala Mayor Kent Guinn.

“I’ve read a couple of books out of the mayor’s office. The titles catch me, and they’ve been some really good books. Mitch Landrieu, former mayor of New Orleans, sent the mayor a copy of In the Shadow of Statues,” she recalls. “He’s talking about his awakening, his awareness to how a lot of the Confederate monuments impacted his community and his friends who were African Americans. And it had never dawned on him that their presence was so oppressive until he finally asked and they told him and he felt like, ‘How can I be so insensitive to that, how could I not see that this was a problem?’”

The book outlines Landrieu’s mission to remove a statue of Gen. Robert E. Lee and Wilson says the original contractor for the job received death threats and the subsequent contractor worked anonymously.

“They had to change their whole way of doing business because of what happened. Just to get these statues removed,” she explains. “And you know what’s going on right now. It’s a topic of discussion everywhere.”

“I talk to people on both sides and it’s like both sides want to come together and we do for a little bit, but it doesn’t seem like it’s lasting,” she offers. “I’m hopeful that as we continue to promote unity that we will get better at it, better at conversing with each other. Because once you get to talk to people, you find out that you have many things in common. I’m sure there are many, many things we could connect on if we just take the time to do it. When I’m at different places, I try to listen to what other people are chattering about and I often think ‘I can be part of that conversation easily.’ But if you’re not invited into a conversation, you just get left out. We should work on being more inclusive, bringing everybody to the table. I participated in the last REACH (Racial Equity and Cultural Harmony) event (Reach Across the Table). That was a great event and I think we need to do more of that. You have a topic you talk about and you get to hear everybody’s perspective and everybody is open and honest about how they feel.”

She says during that event, she talked about working for the city for 20 years and being introduced to a lot of people, but coming away feeling “invisible.”

“I’ve met people at different meetings and at different places and I would know who they are, but they would reintroduce themselves to me over and over. And I was like, OK, we’ve met like four times,” she explains. “I shared that at the REACH event and others had the same experience.”

“Hopefully, people will recognize who I am going forward,” she remarks. “And I’m hopeful that I will be given the opportunity to do the things I need to do for this community. I look forward to working with everybody, and hopefully everyone will get a chance to see my personality. I want them to see my authentic self—who I am, how I am.”

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