Women on the Move in Oxford: From Rebelette to Roofer

Cindy Hale

Cindy Hale has had some rather fascinating life experiences, which is why the Oxford entrepreneur was chosen to lead off a new series, “Women on the Move in Oxford.”

Hale’s life has been anything but dull as the Ole Miss grad has taken a line from Frank Sinatra, “My Way.” HottyToddy.com’s Steve Vassallo caught up with the young lady as she was on her way down from the roof of a recent job.

Vassallo: Cindy, where do we start? How about your childhood, as that’s typically a logical place.

Hale: I grew up in Oxford, having arrived here at age 10 from Kentucky. My childhood experiences have continued to influence me as I learned so much from hanging around with my father. While in the eighth grade, I was contemplating cheerleader tryouts. My dad assured me that if others could do it, then I could. I have never forgotten that logic, applying it to all other aspects of my life.

Vassallo: Apparently, you did quite well in high school as you earned an academic scholarship to Ole Miss.

Hale: The scholarship covered just about all of my college costs. I majored in mechanical engineering initially until switching to accounting. I still had time for four jobs including serving at the “Gin.” One of the hardest things I did while at Ole Miss was being a Rebelette my senior year. I tried out every year of college, but not having any cheer or dance training/experience, it was challenging, to say the least. But the memories are some of the best, and I’ll never forget.

Vassallo: You seem to possess the ability to master just anything you pursue. Share with us what happened following Ole Miss.

Hale: I had a range of jobs/careers including accounting and finance, (director of accounting for the City of Oxford), Parker Hannifin, the Batesville Casket Company, then a stint in the hospitality industry as a financial analyst. The many jobs and knowledge gained lead me to my opening the roofing company.

Vassallo: Your roofing company (Hale Roofing and Restoration) appears to have taken off. Is this a fair assessment?

Hale: I’m now in my fifth year, having completed 120 roofing jobs and about the same number of repair. When I returned to Oxford in 2014 (from Memphis), I made the decision to launch my own solo career and have never looked back. I bring an elevated level of customer service and involvement to each project. People like to understand what they are spending their money on, and I enjoy explaining that.

Vassallo: What about siblings?

Hale: I have a sister who lives in North Carolina and a brother in Nashville. I am likely in Oxford permanently as my father still lives here and my business has continued to grow each year.

Vassallo: Business Network International (BNI) has played an important role in your career in addition to your other experiences.

Hale: I was involved in BNI in both Collierville and here in Oxford.

Vassallo: Any time for hobbies?

Hale: Most of my free time is devoted to my family, raising two teenagers. They are definitely my priority. But, I enjoy fast cars and big trucks. With my eastern Kentucky roots, this is definitely part of my DNA.

Hale has become a role model for many young women and for that matter, anyone who has ever had any self doubts. The highly successful entrepreneur has definitely made an impact in this world, leading her to the “top of the roof” and 100 other places along the way. Like the little engine who said, “I think I can, I think I can,” Hale has proved that she can and continues to do so one client at a time. 


Steve VassalloSteve Vassallo is a HottyToddy.com contributor. Steve writes on Ole Miss athletics, Oxford business, politics and other subjects. He is an Ole Miss grad and former radio announcer for the basketball team. Currently, Steve is a highly successful leader in the real estate business who lives in Oxford with his wife Rosie. You can contact Steve at sovassallo@gmail.com or call him at 985-852-7745.

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